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Key West, Florida
November 29, 2008 - January 23, 2009

As we wrapped up the last trip report, we had just finished a two day passage from Isla Mujeres, Mexico and were moored in the City Marina’s Garrison Bight City Mooring Field off Key West, one of the most famous islands in the USA.

Melissa and I have always unconditionally loved Key West. Before we met each other, both of us had been there and were already in love with the southernmost place in the USA. Key West is remote and tiny, but its physical limits belie its immense historical significance. Most folks think of Key West as a tropical vacation destination, but in fact Key West is one of the most important wartime assets in the USA and it has, time and again, been the lynchpin of successful military strategy.

As such, Key West is a study in juxtapositions and it makes for strange bedfellows: Bombs and Buffett (Jimmy); Gold Doubloons and Reconnaissance Balloons; tourist fishin’ and wartime missions; and, Hemingway and homosexuality.

I find today’s Key West to be much like a flamboyant, crazy, beautiful, delightful, suntanned, leopard-bikini-clad bi-sexual Aunt in cat-eyed sunglasses and black lacquer stilettos who is devilishly misbehaved at all times yet simultaneously perfectly refined as she makes ridiculously exaggerated gestures with a cigarette holder and speaks with genuine eloquence about everything and nothing, all while lounging outdoors all day in the topical shade next to a weathered end-table littered with cocktails in various stages of consumption, an overflowing ashtray, several dog-eared classic novels, an array of skin lotions, and a loaded 45 caliber pistol “just in case” . . . while the wild roosters strutting about the streets and yards give her a wide berth.

Basically, she’s “totally mad,” “packing heat,” and very “conflicted” – and you can’t help but adore her.

Long before we bought Indigo Moon, Melissa and I often snuck away from the cold Christmas weather of Baton Rouge for a summerlike Holiday respite in Key West. It is the single-most genuinely “Caribbean”-like place in the U.S. Mainland due to its southern latitude and resulting climate.

There is much more to Key West than most people know. So let’s take a look at some history.

The first Europeans to arrive at Key West were the Spanish. It was 1521 when Ponce de Leon first landed on Key West. It was named “Cayo Hueso” the pronunciation of which sounds sort of like Key West, resulting in the Anglicization of the name into what we know as Key West.

In fact, the original Spanish name of Cayo Hueso means “Bone Key.” The island was named that because it was littered with Native American bones. The island served as both battle and burial ground for American Indians. As we will see, this is sharply-focused foreshadowing of Key West’s modern day legacy as well.

Great Britain took control of Florida in 1761 and the Spaniards and Indians fled to Havana, Cuba. The Spanish again took control of Florida twenty years later, but no nation was able to exercise de facto control over Key West. It was used by fishermen from Cuba and the Bahamas and the United States after it was settled.

In 1816, the Spanish Governor of Havana, Cuba, deeded Key West to Juan Pablo Salas, a Spanish Naval Officer who was stationed to the north at St. Augustine, Florida. After Florida was transferred to the United States, Salas feared his title to Key West might be in peril. So, he sold the island twice! He traded the island for a sailing sloop worth $575. Then he also sold the island for $2,000 to U.S. businessman John Simonton.

The sloop trader quickly sold the island to John Geddes, a former governor of South Carolina.

In the end, Simonton had greater influence in Washington D.C. and beat out Geddes. Simonton came away with clear title to Key West. Simonton was the original “snowbird” and he spent winters in Key West and summers in Washington, D.C., lobbying for the development of Key West as a strategic military base (such a development would also, by default, bring law and order to the town of Key West). Simonton died in 1854.

And just what the "recipe" of Key West's history needed was to add some Bahamian conch to the pot. Pronounced “conk,” this was the slang name adopted by immigrants from the Bahamas where the actual shellfish known as conch is a basic food staple. The self-proclaimed “conchs” coming to Key West were British Colonialists from the Bahamas who fled British Rule and became Loyalists in the American Revolution.

This is the origin of Key West proclaiming itself to be the “Conch Republic.” These days, the locals consider someone a “Conch” if born in Key West, and a mere “Freshwater Conch” if the person has lived in Key West seven or more years. The truth is that most are not Conchs at all in that to truly be one you had to be of European ancestry and immigrate directly to Key West from the Bahamas.

The Key West Flag: The Conch Republic

Key West was very isolated until 1912 when the overseas railroad was completed by Henry M. Flagler who also created a huge landfill at Key West’s Trumbo Point to serve as railway yards for the “Overseas Railway.”

Soon thereafter, in 1935, what was known as The Labor Day Hurricane destroyed much of the railroad facilities on Key West and killed hundreds of residents, including four hundred WW I veterans.

Flagler could not afford to rebuild the railway, so the U.S. government rebuilt the rail route as a highway in 1938 as an extension of US Highway 1. The start of Highway 1 is in the City of Key West where the famous mile marker zero is located.

Key West is what I personally call the end, bottom chute of the “Plinko Game of Life”, where mentally ill street people and the wildest of the “crazies” on the entire Eastern Seaboard slide and bounce down through the “pegs” of life, and, unable to get a firm hold in society, they finally bounce to the very bottom and come to rest at the end of a road where it is impossible to go further. Key West is as far as one can walk (literally) away from both life and the brutal winters that torture the homeless.

You would probably NOT be surprised that many a person's story begins with (fill in the blank with any horrific personal tragedy or break with society) and the tagline is always: "So I said to Hell with everything and headed for South Florida and the Keys".

Thus, Key West is a natural landing place for the hopeless, homeless, wild, wacky, and eccentric.

Predictably, it is also a natural landing place for the very rich. Just as many stories revolve around "We have done really well financially and wanted a beautiful place to live close to the the tropics, so Key West is a natural."

By its very nature and influx of a tremendously diverse and colorful society, it's not a surprise that Key West has a large gay and lesbian population. The annual Fantasy Fest is a wild Mardi Gras-like street party that takes place in October. Unlike Mardi Gras which has a religious reason for its timing and existence (a last huge party before the Roman Catholic Lenten Season) Fantasy Fest was created for no other reason than to have a huge party and stimulate business. Locals Tony Falcone and Bill Conkle, two Key West businessmen organized the first Fantasy Fest in 1979.

The celebration has grown to be one of the most flamboyant gay and lesbian celebrations in the nation and it includes parades, costume contests, drag queen contests, AIDS fundraisers, body painting and DRINKING . . . lots and lots of drinking. Annually elected, the Conch King and Queen of the Fantasy Fest are chosen from candidates that participate in an AIDS and HIV fundraising competition. The winners ride on the King’s and Queen’s float in the Parade and preside over the Festival. I would imagine, however, that this sometimes results in two Queens presiding over the Festival.

We have never been to Fantasy Fest. Considering we quit drinking and became teetotalers decades ago, those types of street parties hold much less allure for us in our sober old age. The old saying is that "there are only two things you can do with a bad drunk: get drunk with them or get the Hell away from them until they sober up." That said, Fantasy Fest still looks like a blast for those in the hunt for a wild party the likes of Fat Tuesday. Elaborate body paint is an art form unto itself and Key West's Fantasy Fest seems the epicenter for it.

On yet another front, most people know that Earnest Hemingway lived in Key West. Six-toed house cats still lounge around Hemingway’s House in Key West, now a tourist attraction. And you all know who "Poppa" is.

Also, Mel Fisher, the famous treasure hunter (now deceased), found the wreck of the Atocha and made hundreds of millions in Spanish gold and jewels, all out of his home port of Key West. In fact, if you look at a nautical chart and study where the Atocha was found, it will drive you crazy because it is so ludicrously close to Key West. It gives you the sensation that you could have waded out there and scooped of all that gold with a dip net. And it lures you with the real truth that there is a lot of gold still out there waiting to be found.

Last, and not least as to his fans and followers known as "Parrotheads," Jimmy Buffett’s corporate musical empire started in Key West where he honed his brand of what is really country music with a steel drum and harmonica thrown in to sound "islandy" and then with a sprinkle of soft rock-n-roll on top. It's a simple concept and Buffett is a mediocre singer and musician at best, but his product found a niche amongst boaters, beachbums, and those who dream of the tropics. His business savvy turned his tunes about everything "Margaritaville" into a multi-million dollar industry all its own.

Literature, treasure and music all come to mind when we think of Key West . . . such a romantic vision of a topical paradise: adventure, fame, culture, music and fortune all come instantly to mind.

But, the truth is all of that is totally secondary.

Key West’s biggest legacy by far is that of WAR. From its ancient history as a battleground so covered in native Indian bones that the Spanish named it “Bone Island” Key West has continually been the focal point of wars and war efforts on a scale that spectacularly exceeds its tiny physical size.

Here's a review:

1815: Major Outbreak of Piracy

As the War of 1812 waned, Piracy in the Caribbean and South Florida waters was surging. By 1820 the Piracy epidemic was chronic and in that year alone twenty-seven American vessels were robbed, their crews either brutalized or murdered.

By 1822, Congress appointed Capt. David Porter, an 1812 War Hero, to establish headquarters in Key West and command a squadron of shallow draft vessels capable of pursing and eradicating Pirates at their “inshore lairs.” The vessels chosen were eight fast-sailing shoal-draft Chesapeake schooners, five gun barges, and a sidewheel steamer.

From their base at Key West, Porter’s forces patrolled the entire Caribbean and within two years they had virtually eradicated Piracy in southern waters. Porter compared Key West and the Gulf of Mexico as the equivalent of Gibraltar and the Mediterranean.

1835 Second Seminole War

Florida Indians launched attacks on military units and plantations in protest of being removed to western reservations. Key West was in peril and the frigate Constellation was dispatched to protect the island and its citizens.

The Indians had burned a schooner at Tavernier Key and also attacked Indian Key, burning the village and killing five inhabitants.

The Navy forces also controlled arms smuggling to the Indians from Cuba and the Bahamas.

Eventually, the Seminoles retreated after the Navy utilized 600 personnel in dugout canoes (known as the Mosquito Fleet) to pursue the elusive Seminoles, few of which were captured.

1861 Civil War

Only three days after Florida seceded from the Union, in the middle of the night Capt. James Brannan of the Union Army marched his troops from their barracks in the northeastern side of the island to Fort Taylor on Key West’s southern shores so as to prevent Confederate sympathizers in the City from taking the fort.

Key West was the only Union occupied southern port and provided a tremendous strategic advantage and it became the stronghold for the Union’s Gulf Blockading Squadron, patrolling the Gulf and the East Coast all the way up to the Indian River.

The Union Army sent additional troops to finish construction of Fort Taylor on Key West and Fort Jefferson in the Dry Tortugas Islands 80 miles off of Key West. By 1862 there were 900 soldiers at Key West and 200 at Fort Jefferson. The blockade efforts snagged 199 smugglers and blockade runners” during the War and Key West is noted as playing a critical role in the Union Army’s defeat of the Confederacy.

The troops at Key West suffered tremendous casualties, not from bullets but from yellow fever epidemics in 1862, 1864 and 1865.

1898 Spanish American War

In January of 1898 the battleship USS Maine sailed from Key West to Havana to protect American citizens threatened by riots in Spanish-held Cuba. On February 15, 1898, a mysterious explosion sunk the Maine in Havana harbor, killing 261 men.

An inquiry was initiated in Havana and concluded in Key West’s Customs House with a finding that a submarine mine most likely sunk the Maine but was not able to determine who was responsible.

Key West’s harbor was mined and all efforts were made for War. The USS Nashville fired the first shot upon an unsuspecting Spanish merchant ship that had no word that War had been declared and blundered into Key West.

It was a brief, three-month War, but at its end the USA emerged as a major world power.

1914 World War I

Key West served as a major naval training base during World War I.

By 1915, the Naval Station included 101 acres, 55 buildings, 50,000 ton capacity coal sheds, machine shops, a 750 ton marine railway, a hospital, and hundreds of personnel.

Development continued and a Naval Air Station was added, with a Curtiss N-9 seaplane taking off from the near-completed facility on September 22, 1917. The Air Station included a large blimp hangar, seven seaplane hangars, three seaplane ramps, barracks, mess halls and shops.

During World War I, 500 naval aviators were trained there and it was the largest seaplane training center in the USA with almost 1,000 men stationed there.

Navy surface ships patrolled the Straits of Florida to block enemy submarines and surface ships. From the foot of Duval Street, destroyers, sub chasers, and patrol craft conducted operations.

By 1920, a submarine basin was in place as well.

As if that is not enough, Thomas Edison resided at the Naval Air Station while developing underwater weapons for the U.S. Military.

Once again, Key West was strategic in waging successful warfare, this time a World War.

1939 World War Two

Soon after War broke out in Europe, President Roosevelt visited Key West and ordered it reopened to keep German warships and subs out of the Caribbean. The Navy expanded to 3,200 acres of developments and added a new Fleet Sonar School.

An ammunition base was built on nearby Fleming Key and the military and civil-service personnel grew to number in the thousands.

Despite U.S. efforts, German “U-Boats” managed to damage/sink 102 ships by 1942, two of them just 12 miles from Key West. A convoy center and control method was successful in reducing the sinkings to only four in 1943 and none thereafter. 15,000 personnel routed 8,000 ships and 18,000 trained sonar operators worked to detect and track submarines.

Again, the strategic location of Key West and the training and development that occurred there is credited for playing a major role in the USA winning the Battle of the Atlantic in WW II.

1948 The Cold War

After WW II, Key West was maintained as a military stronghold in light of the deteriorating relations with the Soviet Union. Key West became the largest anti-submarine warfare training center on the East Coast and by 1948 Key West’s military operations were so large that a rear-admiral commanded the naval base.

Advanced Underwater Weapons schools, Underwater Swimmers Schools, Ordinance Units, and the most cutting edge methods of naval warfare were developed and refined. Also, Navy and Marine Corps fighter squadrons trained at the Boca Chica Naval Air Station where an “aggressor squadron” simulated air-combat tactics that would be employed by the enemy.

Over 20,000 personnel participated in all these efforts during the 1950’s and 60’s, far outnumbering the civilian population.

President Truman spent eleven working vacations in Key West during the Cold War, spending so much time there his accommodations were dubbed the “Little White House” and during a meeting with all the Chiefs of the Armed Forces the Department of Defense was created to unify our military branches. Known as the Key West Accords, once again, the little island of Key West had a big impact on our military history.

1962 The Cuban Missile Crisis

On October 15, 1962, Key West was swarming with activity following the discovery of nuclear missile installations in Cuba. Troops flooded into Key West and its fleet of destroyers and submarines went to sea.

By October 22, President Kennedy ordered a quarantine of Cuba surrounding it with U.S. ships, subs and aircraft all while Key West was fortified with barbed wire and bunkers on the shores that included machine gun and anti-aircraft batteries. Troops guarded bridges and pipelines connecting all of the Keys to prevent sabotage. Planes flew hundreds of patrol missions.

On November 20, 1962, President Kennedy and the Joint Chiefs of Staff met at the Key West Naval Station and lifted the quarantine.

Yet again, Key West’s facilities and military presence was instrumental in our survival during extremely serious world conflict.

1980 Mariel Boat Lift

On April 21, 1980, the first boatloads of Cuban refugees arrived in Key West. Hundreds of persons were overloaded on unseaworthy vessels and the Coast Guard only had 140 personnel and one cutter. Within two weeks, the Coast Guard had 600 personnel, nine cutters, numerous 40 foot utility boats and several helicopters working the situation.

Navy ships and aircraft conducted patrols and all parties assisted in scores of search and rescue missions to save lives of refugees in peril. In the end, over 125,000 Cuban refugees arrived in Key West and due to the heroic efforts of the Coast Guard and Navy, only 27 refugees perished at sea.

1989 War on Drugs

Key West’s location on the Straits of Florida, situated between the Caribbean Sea, Gulf of Mexico, and Atlantic Ocean makes it a critical gateway for drug trafficking and, therefore, a vital location to wage war on drug smuggling from South and Central America.

Efforts to reduce drug trafficking through the region began as early as the 1970’s. Much success was made in eradicating marijuana smuggling, but just as that problem was under control, cocaine smuggling began to increase and much of it shipped by sea.

In order to address the problem, the official War on Drugs resulted in President Bush’s Joint Task Force 4 wherein the Army, Navy, Air Force, and Coast Guard worked in unison. Soon the DEA, Customs, and FBI joined in as well as warships from Great Britain, France, and the Netherlands participated too.

These efforts have been very effective, so much so that the cocaine smugglers have shifted their routes from Colombia to countries in Central America such as Guatemala and into the United States through Mexico, and thus the current, bloody drug wars in Juarez near the U.S. Border have resulted.

The message is clear: for almost two centuries, this tiny little island named Key West has had a phenomenally profound military impact on the world.

During our stay, the peace of our quiet mooring field was often jarred by the explosive sound of fighter jets roaring out of nearby Boca Chica on training missions. Key West is still home to one of the U.S. Navy Top Gun fighter pilot schools and the Coast Guard has a powerful presence and fleet of ships and boats that patrol the Straits of Florida.

And so, while Cruise Ships and tourists come and go, and the T-shirt shops and bars on Duval Street cater to the partiers on vacation, Key West is still a military stronghold and will always remain so.

Now that you know more about Key West’s history and personality, let’s put on our tourists’ hats and take a look around! The best place to start is with both an aerial photo and map of the island so you that you can understand the lay of the land and the locations of the various bays, cuts and waterways we’ll be referring to in the report.

Map of Key West (see a larger image of the map with explanation here)

KEY WEST MAP (see a larger image of the map with explanation here): Starting at the lower left corner of the island, you see:

1. Fort Zachary Taylor and the Naval Reservation. We’ll start there and begin working clockwise around the island. The Florida Keys Eco-Discovery Center is located in the area where you see the words “U.S. Naval” located on the map. There are also some Navy vessels on display moored to the seawall;

2. Just north of the Naval Reservation is a large basin. The outer seawall of the basin that is used as cruise ship docks; the basin itself is too small for cruise ships, but there is a marina there. That marina is not popular at all because it is too open to the seas and to the wakes of large vessels, and the seawalls and docks are too commercial;

3. The Truman Annex neighborhood and The Little White House is located in the long rectangle (would be a rectangle but for the one angled end to the northeast) of streets that boarder the south end of that big basin;

4. The Custom House as indicated;

5. A small area of seawall that juts out into the sea north of the Custom House and south of the Aquarium; this is where the Crazy Cat Man does his sunset circus act with trained housecats;

6. The Aquarium and several small malls with trinket and seashell shops for the tourists;

7. Just above the Aquarium is Mallory Square, the small green patch bordered by the Aquarium, Wall Street and the annotation “Chamber of Commerce”; when the cruise ship dock/seawall to the south is full with two ships, then a third might just be docked at Mallory Square and this can interfere with the sunset celebrations;

8. Mallory Square does not look directly west. As you can see, it faces slightly north of west. As such, the setting sun is visible all the way to the horizon from Mallory Square (or anywhere along the promenade that runs from the Truman Annex all the way to Mallory Square;

9. The islands to the northwest are as follows: 1) Wisteria Island is now re-named Sunset Key and it is a super exclusive, MEGA expensive residential island now. There is a ferry that runs from the basin to the island, and you can go have lunch there and wonder what it would be like to have enough millions to buy a mansion on one of the most exclusive islands imaginable and then try and insure it against hurricanes; and 2) Christmas Tree Island, which is not named on the map. It remains an undeveloped, low lying, scrub tree island.

10. Back on shore, directly to the west of Mallory Square is the Key West Bight. It is THE premier marina and recreational boating area. It is beautifully protected and all things nautical happen from the Bight: fishing charters, sunset sails on all sorts of vessels including authentic wooden schooners, ferries to the offshore Dry Tortuga National Park, ferries to Fort Myers, Scuba diving, the Annual Sailing Regatta, and all sorts of action is going on. And of course, the perimeter of the Bight is lined with famous watering holes like the Schooner Bar and famous restaurants like the A&B Lobster House and Turtle Krawls;

11. Following the shore northeast of the Bight, you see three fingers pointing west northwest. That area is the US Coast Guard base and there are BIG vessels like Cutters, sometimes even a submarine, and all sorts of military action going on. As you can see the, larger annotation for the whole adjacent area to the south east is “US Naval Air Station Annex” and in fact all of the areas above Whiting Ave and Palm Ave are restricted Navy Base areas, including the entirety of Fleming Key which is, among other things a HUGE ammunitions reserve;

12. The waters surrounding Fleming Key;

A. The West Side: is controversial because locals who used to be, or maybe never were, cruisers like to anchor off the west side of the island and get in close. The NAVY does not like that and considers it a security risk. The area is a very poor anchorage anyway. For one thing, the bottom has a lot of turtle grass and anchors do not hold well. Many locals have made moorings, and sometimes you can rent one if you get to know the locals. But, because this area is totally exposed to the north and east, the little indentations provide little real cover from the fierce cold fronts that blow hard from the northwest all winter. And the current RIPS through the area between Fleming Key and Sunset Key and reverses with the tide, challenging anchoring conditions even more so. There was a rift heating up between the NAVY and local boaters during our stay. There is ONLY ONE reason anyone in their right mind would anchor/moor there anyway: location, location, location: it is one of the few places you can anchor within a short dinghy ride to the Bight;

B. The East Side: this is where we stayed and it can only be reached by following a channel up the west side and around the top of Fleming Key and then down the East side where the shallows give way to a larger navigable area. It is here that the City of Key West installed 250 moorings . . . a GIANT mooring field that is totally exposed to the north and can be ROUGH. And that also means long dingy rides in rough conditions. It is called the Garrison Bight Mooring Field, but it is NOT in the Garrison Bight (that you see on the main island and below Trumbo Point). In fact, there is no clear view of the Garrison Bight Mooring field from any public property. The northern border of the actual Garrison Bight is all NAVY base. As you might imagine, the mooring to the very lower left corner were the most sought after because they make for a shorter dinghy ride and are the most protected from north and northwest winds in cold fronts. To get to land from your boat you get in the dinghy and; 1) go east and under the bridge to Fleming Key (not tall enough for any sailboats . . . just fishing boats can pass) and go all the way around the USCG base and into the Bight and pay $5 to tie up at a marina dinghy dock; or 2) go south into the Garrison Bight and to the dinghy dock all the way to the southwestern corner of the bight and on Palm Ave, or go under the Palm Ave, bridge and into the “yacht basin” and to a dinghy dock at the far eastern corner where the Marina/Mooring Filed Office is also located. This dinghy dock fee is included in the mooring rent, but it puts you nowhere . . . it’s a long walk to Duval Street, Mallory Square, the Key West Bight and the touristy areas, and also a LONG walk east to the modern areas of Key West like the supermarket, Home Depot and Walgreens. The bottom line: Key West is a very inconvenient place to access by dinghy. We did some LONG WALKS for months, sometimes as “pack mules” with tons of groceries etc. and in many ways Key West is a bitch to visit on the boat. Nonetheless, we loved it and it was worth the trouble.

Many of the boats in Key West (and in the Mooring Field) are totally BUM BOATS that have no masts, are is terrible disrepair and are used as cheap housing for those who work low paying jobs in Key West. Some are just homeless people on derelict boats. In fact, I would say that derelict boats and homeless people in general are a significant part of the fabric of Key West. NOT depicted on the map are some small keys just north of the cut in to the Garrison Bight . . . these little islands are not developed, but homeless folks bums have set up shop and have tent camps and such on them. It’s the homeless folks version of Sunset Key. It seems there really is room for everyone in Key West;

13. Garrison Bight: this bay has a LOT of skinny water. There are some docks to the south east of the Bight where it says Yacht Basin. And the south shore east of the Palm Ave bridge has huge houseboats (camps on barges);

14. The inner yacht basin at Garrison Bight: this is where much of the offshore charter fishing fleet had set up shop. There are about 20 large sportfishing boats backed in stern-to Palm Ave on the seawall and as you walk by, they “hawk you” with “wanna catch a big fish today?” or “the Mahi Mahi are tearing it up out there today . . .”;

15. Continuing along clockwise, there is a large island accessed by Byrd Road and it is all restricted NAVY base;

16. Moving along to the area where you see a number “5” on the street, this is the “modern” area of Key West: shopping centers, PUBLIX, Walgreens, Searstown, Outback, Big John’s Pizza, Cinema, Home Depot, Radio Shack, doctors’ and professional offices, etc.;

17. The bridge to Stock Island: this is the only way onto and off of Key West by land. This is significant when hurricane season arrives;

18. Stock Island: this island is a mix of commercial fishing and resort communities and marinas . . . just one little bridge and one little Key away and ALL of the charm of Key West is gone. Stock Island is just another Florida Key in its character (or lack thereof). I have always found all the Keys (except Key West) to be of little real interest themselves and with very little to offer except the emerald water surrounding them. History agrees. Everything of true moment historically happened on Key West;

19. South of the bridge to Stock Island is Cow Key Channel. Shallow but very well protected from the north and from cold fronts, this used to be called houseboat row and was a huge shanty town of terribly unsightly houseboats. It has been significantly cleaned up nowadays;

20. At the southeast corner of Key West, just past the Salt Pond and directly inland of the street, is an old fort that is not depicted on the map;

21. The airport where commercial flights come and go (all small puddle-jumper turbo props like American Advantage) and also where you can take a ride in the venerable old Orange Bi-plane that has room for two up front and the pilot in the back. Also, a local pilot maintains a very small and fast stunt plane here, and he sometimes shows up over Mallory Square and puts on a free show of amazing aerial stunts . . . just for the fun of it;

22. Along the southern shore, there are some beaches, but none natural. Sand has been pumped in. Key West is coral, not sand. And the shores off the south are situated on what is known as Hawk Channel, not the Sea. There is actually an offshore reef that separates Key West from the deep blue sea. Unfortunately, what this means is that the beaches are second rate at best. The shallows run for a long way. There is no surf and the water is not very clear as the bottom is covered with grass and weeds. That did not stop development, however. There are resorts and mansions on the shore, but there are no marinas, the area is too shallow for any recreational boating, and it is not the most popular area of Key West;

23. At Monroe Beach there is the stunning Casa Marina Hotel built by the Railroad Barron Flagler. The resort has extensive grounds and swimming pools and offers a fabulous Christmas Buffet Dinner that Melissa and I have enjoyed in several different years . . . as fly-in tourists and now as folks passing through on a yacht;

24. City beach at the corner of South Street and Whitehead Street is also where the famous Southernmost Point marker is located; and,

25. Finally, Duval Street runs from near Mallory Square all the way across the island to South Street, just one block east of the Southernmost Point marker. Duval to the north hosts famous bars like Hemingway’s favorite Sloppy Joe’s and The Bull. You'll also find restaurants and other tourist attractions like Ripley’s Believe it or Not and Hard Rock Café. And then midway down Duval it’s Gay! In the center of the island on Duval St. clubs like “Q” and all make guest houses and such are open for business. Toward the south end of Duval the art shops take over and also, further south you can visit the Key West Butterfly and Nature Conservatory, just one block up from South Street.

That is a very nice introduction that will help you get your bearings.

Also, here is an actual photo of Key West:

The shallow water of the Florida Keys can be appreciated here: the saying is "Brown Brown - go around: Blue Blue - go on through." Only the Deep Blue channels are navigable.

Pay particular attention to the color of the water. Any area that is NOT DEEP BLUE is very shallow. You will see the extensive shallows of the south shore, the shallows off of the cruise ship docks and Mallory Square, the Tidal Channels that funnel FAST currents through the area, a Cruise ship on the seawall of the large harbor, Sunset Key fully developed and Christmas Tree Island still green, the dark green channel that rounds the top of Fleming Key allowing access to the Mooring Field on the east side, and that the extensive shallows that helped make salvage and wrecking companies very rich. Finally, look closely at the deep blue water that rims the western end of Key West and you will see three boat wakes of vessels headed south out of the channel to avoid the brown shallows directly to the west. You’ll also notice a boat wake following a very thin blue channel and headed southwest, just at the edge of the photo. Make a mistake in the Keys and drift ever so slightly out of these narrow channels, some natural and some manmade, and you’ll be hard aground and sometimes on coral! Fines are very STEEP for doing any damage to the bottom, even grass. So, the Keys, including Key West, mandate a careful touch on the helm and total orientation and planning before getting underway.

OKAY! Whew! That’s a lot to digest!

No better place to begin a tour of Key West than with the "dog and pony show" of Duval Street. At the west end of Duval, tourists from cruise ships at the nearby docks fill the street on their way to see everything from T-shirt shops, to clothing optional barrooms, to Hemingway’s famous haunt Sloppy Joes Bar, to very pricey art and antique shops.

It’s quite an intoxicating mix for the senses, and perhaps one of the most powerful ingredients is the subtropical climate itself. I have always loved the tropical sun’s resulting patina upon life, not only the way the weathered buildings and the tropical plants are set against brilliant sun and black shade, but the tropical pace of life itself. There is a natural “metronome” adjustment that slows the cadence of life in Key West, and there is a synergy of architecture, climate, eclectic personality, and unusual history that makes Key West one of our favorite places.

There is a lot of wonderful history, architecture, and beauty to behold in Key West that has nothing to do with night clubs and restaurants, but as to Duval Street, it’s all about the party in the same fashion that Bourbon Street serves one singular purpose in New Orleans. The challenge is set forth as the “Duval Crawl” for those willing to work their way all the way down Duval and have a drink at every bar on the street so as to eventually no longer be able to walk and have to crawl from severe intoxication. Of course, Melissa and I stayed sober and we didn’t do any crawling, thank God! We did enjoy the scene though.

At the west end of Duval, one of the many “conch train” tour rides enters the intersection with its P.A. system blaring historical facts about Key West while tourists ride along.

Sloppy Joe’s Bar, where T-shirts are adorned with a portrait of Hemingway.

Another famous watering hole is The Bull, and we always laugh at the hokey, funky bull with glowing red eyes.

We were too chicken to go upstairs to the Garden of Eden.

Some bars are pretty small. Here is “The Smallest Bar in Key West” and you are seeing ALL of it . . . it is a totally open air bar in a tiny alley with nothing but what you see here. Even though the bar is small there is a pretty big party going on!

The heartbreak of homelessness, addiction, and mental illness is a permanent fixture of Key West and Duval Street and its side alleys in particular. Here there is a disturbing and illuminating juxtaposition of happy party slogans for sale in the window, but a harsh reality of misfortune for some out on the streets.

There is a noticeable society of homeless people in Key West. And we interacted with that society often during our stay. As cruisers, and never having a car, over the years we walked long distances (anything less than ten miles is a stroll to us now), rode buses, and mingled with those along the way who are in the same lack-of-transportation situation, not as a choice but because they are destitute.

So, conversations spring up and over the years I had a wonderful change in my tolerance for taking time to converse with the mentally ill. One time, while waiting on a prescription to be filled at Walgreens and sitting in the little waiting area, a clearly mentally ill lady sat down next to me and struck up a conversation. Melissa was browsing the nearby aisles and could hear part of the conversation that went on for a good fifteen minutes. I got my prescription and wished the lady well and headed for the front of the store. Soon Melissa was in tow and she said “I can’t believe how you sat there and talked to that lady. You never would have had the patience for that before we went cruising.” Indeed.

We had many interactions with the homeless and down-and-out, but one sticks out as the funniest. Melissa and I had walked all the way to the Searstown shopping center and gone to the movies. When we got out of the show it was dark. We decided to splurge and catch the bus back to the dinghy dock, so we went to the bus stop to wait for the next bus.

There were two homeless guys there, one a very young long-haired kid who was a newbie in Florida . . . you can tell . . . they are too jittery and have not relaxed yet. He was too white and too fresh to have cooked in Key West for a whole season. He was very distressed and could not talk very well because his jaw was broken. Apparently, he had been beat up near the Bahamas Village section of Old Town the night before. The other guy was older and a weathered Key West resident of the streets and was trying to give street savvy advice to the young guy.

We were all at the bus stop. My cell phone rang. I had a quick conversation with a friend and hung up. About that time I made eye contact with the kid and said “Hi.” He immediately struck up a conversation and through a clenched jaw, explained he had no money, was stranded, need to call his family and wanted to use my cell phone to call home. He began to explain why he could not move his jaw. As I began to actually have a conversation with the young man, that instantly broke the ice and the other guy chimed in too, both of them eager to tell their stories to Melissa and me, even though we were clearly not members of their homeless society.

I let the kid use my phone, but must admit I was doing some stretching of my ham strings and getting ready to sprint after him if he bolted with it. He did not. He was just a really scared kid: terrified, homeless and now beat up in Key West. The other gentleman continued to chime in and tell his story too, all while we waited for the bus.

Things were going well with our bus stop party, and then the fresh kid asked for money. The seasoned homeless guy instantly turned and glared at the kid and said “DON’T PUSH IT KID!” and then in a millisecond turned back to us smiling and continued talking as if nothing happened. Melissa and I still use that line for shorthand “DON’T PUSH IT KID!” when we think either of us, or someone else is Gilding the Lily.

Taxi drivers are also a hoot in Key West. If you want to hear the tallest tales on earth, just get in a cab. Chances are you'll hear a tale of how the cabbie got there and where he or she plans to go next in life, and it is always stunningly unpredictable and akin to "back when I was CEO of General Motors . . . . blah blah blah . . . and I am only doing this to take a break . . . next year I will be President of Brazil . . . blah blah blah . . ." It is very entertaining if you just relax and have a conversation despite a total suspicion that nothing could possibly be true about what you are hearing.

I can’t really explain why, but there is just something in the ether in Key West that fosters acceptance and tolerance. Surely the extremely diverse fabric of society has to play a part, in and of itself, but there is in my estimation some type of unique magic in Key West that you can’t see but can readily feel, just like the tropical breezes there.

And so, back to Duval Street!

Just like New Orleans’ French Quarter, but on a much smaller scale, bars and junk shops and other tourist trap businesses are mixed-in with some great places to eat, some old and some new. The nice thing is that the architecture has been kept tasteful and it makes for a nice atmosphere.

Places like Bagatelle have dining on the upstairs porch, providing a bird’s eye view of Duval Street and all its goings on, all while enjoying very fine food. And there is much to see.

Bagatelle restaurant on Duval has fine food and a great view of Duval Street.

Even the Hard Rock is pleasing to the eye.

This is the most unusual Walgreens we’ve ever seen

How about a motorcycle with a V-8 engine?

T-shirts of all kinds . . .

Street performers earning their dinner

Now, as for the gay thing . . . yes, Key West has developed a reputation as a popular destination for gays and it’s clear that the gay population is accepted and has a comfortable place in Key West society. There are all male guest houses, gay nightclubs, and drag queens are a common sight on Duval street at night. Some are better at walking in high heels than others, and watching that is a sport in-and-of-itself.

New Orleans House, an all male hotel

With the Rainbow Flag and a capitol “Q” serving as its name, a stop in this club would probably make the Duval Crawl that much more interesting!

It's true that the gay scene in Key West is off-putting to the homophobic, and I have even had some folks malign me when I profess a deep love for Key West: “Key West?! You like that place? What, are you queer?

No, I’m not gay and yes, I love Key West . . . ALL of it. So what? Everybody gets along in Key West and it is a “live and let live” atmosphere where people appreciate diversity and do not fear it.

The fact is that one of Key West’s most wonderful attributes is that while it's a tiny little island, nonetheless it has room for everybody from all walks of life. Melissa and I love that about the island. It is packed with unconventional diversity and a seemingly effortless acceptance of it.

That said, there is so much more to Key West than Duval Street. Let’s venture out and look further.

We love the architecture of Old Key West. Its Spanish period resulted in the customary Forts and designs we found throughout the Caribbean and New Orleans.

Much of the residential architecture is akin to Acadian and plantation type structures we love in Louisiana.

On top of that, there is a twist of architecture known as “eyebrow” houses. The term denotes that the second story windows on the front of the house are totally protected and set up under the front porch ceiling that extends out and then drops down several feet like a big eyebrow that protects the windows from rain and winds. This style allowed the windows to stay open and the house to stay well ventilated in the tropical heat, even if it was blowing a gale and raining cats and dogs.

Here's a look:

With the upstairs windows shielded from weather, this Eyebrow style house can be well ventilated even if its raining.

Beautiful southern styling

Stately tropical living at its best

One of the most beautiful residential areas in Key West is situated in the Truman Annex. How did it get that name? Well, there is a famous house on the island that has quite a history. Today it is known as “The Little White House” as a result of President Harry Truman’s extensive use of the house during his term from 1945-1953.

President Truman spent eleven working vacations there, and many important decisions about our nation were made here in Key West. President Taft was a visitor in 1912. Eisenhower used the house in 1955. JFK used it for a summit meeting with the British Prime Minister just 23 days prior to the Bay of Pigs. The base was named the Truman Annex after Truman’s death in 1973. It was closed by the Navy soon thereafter and remained abandoned until 1987 when it was transferred to the State of Florida and a restoration was undertaken to reflect the Truman era.

It is, quite frankly, one of the coolest neighborhoods in the world as far as we are concerned.

The Little White House has hosted a lot of Presidential visits

How can this possibly be improved upon? What a wonderful home under the palms.

The Truman Annex: one of the most desirable neighborhoods in the world if you ask me.

And while the prefect restorations and new constructions in the Truman Annex are awesome, there is also the charm and history of true historical structures in Old Key West. Like most places this spectacular, the prices are through the roof. It takes a million dollars to get something modest and more millions to get a really fine home. We still buy a one dollar lottery ticket now and then . . . and if we hit the jackpot, a vacation home in Key West would do quite nicely!

Decked out for the Holidays, this circa 1800’s house is nice

The cat caught the rat

LOOK how cool this is: totally tropical landscaping year round, no freezing weather, and one hundred percent of the charm of architecture found in the antebellum deep south; this is pretty close to heaven

Some mansions are of a design all their own, like this pastel castle of a home located on the shore near the Southernmost Marker

The Holiday Season is laid back in Key West

There are also many old structures that have a category all their own

It’s Christmas, but the Bougainvillea don’t seem too worried about it

The Curry Mansion Inn is huge and at the very top you see a small rectangular, railed porch called a “widow’s walk” and legend has it that wives would use these platforms to scan the horizon for ships that were overdue and carrying loved ones. Here, the whimsical owner actually has a mannequin up there and with a spy glass she searches the sea.

And, of course, perhaps the most notable and well known house on the whole island: Hemingway’s home where he lived in Key West. People pay to tour the home and see where “Poppa” lived. And descendents of his six-toed cats still remain, still lounging around the tropical grounds of the mansion. It is easy to see how this lush, tropical setting helped “Poppa” spin tropical tales.

Open 9 to 5, for 12 bucks you can tour Poppa’s house

Lush grounds of Hemingway’s Key West Home

Through the gardens, you can see the wrought-iron porches of the home

Here Kitty Kitty! Let me see those six toes on each paw! Hemingway’s home is famous for the population of cats that do actually have six toes!

The entirety of Key West has that fabulous patina of the tropics, where the sun blazes and bleaches the buildings and structures as if finishing off the top of Crème Brule, all while feeding the exotic vegetation that makes Key West one of the most tropically alluring destinations in the USA.

But so what? That does not in and of itself make Key West unique at all. The tropics proper make up a large portion of Earth and spans oceans and continents. Thus, while Key West’s architecture and climate form a very attractive backdrop, it is the mix of people of Key West that set it apart.

There is no better place to start than the Sunset Celebration at Mallory Square. Facing west to the horizon on the sea, it is the perfect place to join the crowds and watch the sun dip below the horizon. The hope is to see the phenomenon known as the “green flash” wherein the air is so clear and the dust level so low near the surface of the earth between you and the setting sun that when that last tip of sun disappears it looks like it leaves a yellow-green flash directly on the horizon for a second or two.

And hey, since there is a crowd in Mallory Square already, why not make it a celebration. Put another way, if you are a street performer, artist, musician, food vendor, jewelry craftsman or whatever . . . Mallory Square’s sunset popularity produces a dependable stream of potential customers and that is one of the windows into the uniqueness of Key West. For example, I have never heard of nor seen a circus act of trained housecats. Add in a barmy French trainer who is unpredictable in the extreme and it is one little element of true uniqueness that makes Key West one of a kind.

There is a lot going on in Mallory Square in the late afternoon. Old wooden sailing schooners sail by on their sunset sails. For the aware (aka sober enough to realize what they are looking at), gazing upon a horizon with only old sailing schooners upon it is delightful and one instantly realizes that this was the exact view over 200 years ago.

But then, in routine Key West juxtaposition, just as I decided that I was an 1800’s salvage “wrecker” gazing out to sea (more on them in a minute), watching these sailing schooners to see if they would hit the reef and bring me a big payday, my thoughts of the old days were totally shattered by a Coast Guard vessel coming into view and doing about ten knots in reverse . . . and it kept going in reverse all the way past Mallory Square all the way to the Coast Guard’s docks a mile past the square . . . just like a five-year-old running naked through the living room at her big sister’s piano rehearsal, it was just plain wacky.

There is an Aquarium adjacent to the Square, there are seashell shops, gift shops, restaurants (including a pretty good Cuban one), bars, and the Key West Shipwreck Historium that has live shows. During our stay, they were looking for an actor and I resisted applying despite Melissa’s goading for me to join the ranks of the “hokey fake pirates with pontificating, exaggerated accents.”

The seawall gets crowded as tourists hope to see the Green Flash when the sun dips below the horizon; in the distance is Christmas Tree Island.

One of many wooden schooners out for the sunset sail

Okay, this Dude is totally freekin' whacked! His show is over the top and he actually gets housecats to put on a circus show!

With a French accent, he has the affect of a Mad Man while he coaxes his cats and mercilessly taunts the crowd.

HOORAY! The leap is successful!

You’d probably bet that a housecat would never jump through a burning hoop on command; you’d lose . . . I saw it with my own eyes and still don’t believe it!

I see you! One of the cats watches from inside the cat carrier . . . the equivalent of a tour bus for this performing artist

Of course, there are many street musicians around Mallory Square

And just when you think you have seen it all, a Coast Guard vessel goes by in reverse at about ten knots and keeps going . . .

Looking inland, just south of Mallory Square, is the Key West Aquarium

One of the oldest landmarks on the shore near Mallory Square is the old red brick Customs House. It’s been a landmark for a long time and is now a museum, complete with art sculpture displays on the lawns that change often. One day it’s nude nymphs dancing, the next a construction worker.

The only bigger landmarks are often tied to the docks: cruise ships! Disney, Royal Caribbean, Carnival . . . they all come and go. When three ships are in, they BLOCK the view of the sunset at Mallory Square, which makes the tourists VERY upset, as you might imagine.

There is no doubt about it, the advent of cruise ships changed the vibe of Key West and resulted at least to some degree in the development of chain restaurants like Planet Hollywood and Hard Rock, and all the other junk shops that cater to the cruise ship crowds.

Luckily for Melissa and me, we were there for months. And many days there were no cruise ships in and we had the place “all to ourselves” so to speak. And that was so cool!

Old Custom House of Key West

On the cruise ship dock today: Disney is in town

Now, let’s shift gears and talk about the wreckers of Key West. Wrecking (known today as salvage) was the first real economy for the island. By the mid 1800’s Key West had the highest per capita income in the entire United States as a result of the lucrative salvage business.

Even modern day mariners with precise charts, electronic depth sounders, and GPS plotters still manage to run aground, hit reefs, and sink vessels in the “skinny” water of the Florida Keys. The waters of the Keys were, and are, treacherous and command great respect.

There is quite a tribute to the wrecking history of Key West. There is a fabulous metal sculpture near Mallory Square by Miami sculptor James Mastin that depicts wreckers in action saving both lives and goods awash after a shipwreck.

Wreckers monument near Mallory Square

A closer look at the quality of the monument

And then there is the Shipwreck Historium that offers live performances about wrecking . . . fun for the whole family.

Hokey Shipwreck Historium where Melissa wanted me to apply for an acting job

And if all that is not enough, there is an actual wrecker’s sloop on display, providing tourists with a firsthand look at what a working salvage vessel looked like. MARY sits on her keel outside the seashell shops and the Shipwreck Historium and is interesting to see.

According to the placard “almost every seaworthy vessel at Key West quickly responded to the exciting cry of “wreck ashore” to earn whatever share they could in the great wealth of the Golden Age of Wrecking . . ."

MARY, a wrecking sloop is . . . well . . . now a wreck itself

MARY, another view

While strolling between the various displays and attractions, there is no shortage of souvenir shops, and there are some of the most extensive seashell shops you’ll find anywhere.

She sells LOTS of seashells by the seashore

Nice Conch shells for sale in the Conch Republic

Key West is a favorite haven during the Christmas Holidays and New Years, and the tourist season kicks off for real in January. We were there from November 29th to January 24th and that allowed us a long enough period to get a quasi-resident feel for the place.

If I had to list the top five advantages of a cruising adventure such as the one we undertook on Indigo Moon, one would certainly be the ability to stay for months in places you love. Bonaire, Cartagena, Colombia, Washington DC, Key West, the Virgin Islands . . . these are all amazing places we have actually lived in for a time, not just visited. It is a different dimension. After you are cruising a while, you can’t even imagine going somewhere for just one week, or a long weekend, God forbid.

You get spoiled. While those on quick vacations and cruise ships make fast passes through the souvenir shops and select T-shirts and trinkets with the slogan of the day, we were afforded the most precious commodity that can’t be purchased: more time . . . time to really become totally familiar with destinations that we loved and experience a true feel for the societies and people of the places that struck a chord with us.

Key West is fun to get to know over the Holidays. For one thing, it is just so cool to see Christmas lights on palm trees and know it's Christmas while wearing shorts in the balmy tropical weather. Add to that the arty, diverse, and eccentric participation of the locals in the Holidays and it makes for a fun time. Also, Key West’s Annual Regatta takes place during this time as well.

Let’s make a pass through the streets and surrounding waters of Key West and get a total feel for the place.

Let’s start out with the streets. And what more famous street landmark than mile zero of US Highway 1. Yep, the end of the line, or is it the beginning? Well like all things in life, it merely depends on how you look at it and what you decide to do. Go south and it’s the end for you, But go north and it’s the beginning.

Melissa said it was the end.

I said “No, Dear! It's the beginning!"

There is a lot to see in Key West and a lot of history to appreciate. One of the most effective ways to get acclimated quickly is to take the Conch Train Tour. This open air excursion sort of resembles the baggage carts and the tugs that service airliners, but jazzed up in appearance. The tug pulls the carts hooked together. It's one of those miracles that when the whole giddy-up makes a turn somehow the cars all follow one another perfectly and the last car doesn't jump curbs and such.

The Engine of one of the Conch Trains . . . they have several units chugging about town

Here are photos of random scenes taken over the course of our hikes around the streets of Key West:

Blue Heaven . . . the food is great and the dining is al fresco in a back courtyard that has sand for a floor and old sails strung amongst the trees for a canopy; the wild chickens of Key West scurry about looking for table scraps, and it is a very laid back experience that represents the slow tempo and casual way of life in Key West.

Not all residents are so keen on the chickens and roosters running wild around Key West

Any mention of Key West must include reference to Mel Fisher and the museum that displays one of the most valuable sunken-ship treasure finds in US history, This museum, located just across the street from the Custom House, is where you can learn about the late Mel Fisher, his expeditions, and see actual treasure from the wreck of the Atocha.

One of the best music clubs in town is not on Duval; the Green Parrot Bar on Whitehead St. hosts an eclectic lineup of very good musical groups from all over.

Located in midtown and away from the touristy areas, Jose’s Cantina serves up the real thing: authentic Cuban cuisine

Just a half block off Duval, the Cinema Tropic is a charming independent film theater that is quite well funded by the local art scene; on weekday afternoons it hosts educational programs for local school kids and in the evenings and weekends it runs the top Indy films of the day; we watched Slumdog Millionaire there and loved the ambiance of the theater.

I’ll say it again. Key West is compact geographically but offers so many sights and sounds that it takes a while for it all to sink in. As one walks around the senses can be easily overloaded. Every other block seems to have some historical placard or information about the history of Key West, or some eccentric sign by a resident. Look left and there is a modern advertisement; look right and there is a travelers palm that is massive. Walk a little further and look down to see a kitty cat expecting to be petted . . . while an iron Pirate Gate looms above. And all of it adorned with tropical beauty.

One of countless placards around Key West, this one explains the US formation of an anti-piracy fleet in 1822

The birthplace of Pan American Airways, just off Duval St.

A Travelers Palm towers over two stories

Bougainvillea are ablaze even in January!

Modern advertisements mixed in

A good kitty cat life in Key West

There be Pirates here!

This resident is apparently tired of putting up with inconsiderate dog walkers.

Christmas time at the Southernmost Point Marker (being refurbished and missing its lettering) folks are posing for photos in shorts and T shirts; note the Christmas Tree's topping is a tilting quite a bit and nobody cares; that’s “Key West!”

And that brings up another thing: the Holidays. We have been to Key West for the Holidays a couple of years before we owned Indigo Moon. Migrating to the tropics for the Holidays and leaving overcoats and winter locales behind for a week’s vacation in the sun is obscenely enjoyable.

For most of us, being in balmy weather and amongst blooming tropical flora during Christmas is very unusual and dreamlike. Our first visits to Key West were so very unique in that respect. After three years in the southern Caribbean, however, Key West was not so unique in that regard. I only need to recall walking past illuminated, outdoor Christmas Decorations in Cartagena, Colombia, in 95 degree weather and thinking how it was so funny to see snow depicted. In fact, after life near the equator, Key West was a little “chilly” at night and not so tropical after all. But that is good. That meant it wasn't too hot and we didn't need any air conditioning, and it was a very comfortable climate overall.

Nonetheless, I still LOVE seeing Christmas decorations in the topics. There’s nothing like Christmas lights on palm trees and Santa lounging in a hammock. I do think that someone needs to manufacture a plastic Santa in swimming trunks and a Hawaiian shirt, though. He always looks so hot with that red coat on.

As for dinner on Christmas Day we have always enjoyed the Christmas Buffet at the Casa Marina Hotel on the south shore of the island. The first time we attended, as fly-in tourists, the buffet was stupendously grand, with food displays spilling out onto the adjacent porches and the place was packed. Each time we have returned, it has waned. This year, due to the Great Recession being in full swing, the buffet itself did not even rate an honorable mention and the crowd was clearly less one-fourth what it was in the late nineties when we first began enjoying Christmas at Casa Marina.

That was a depressing feature of this year’s Christmas in Key West and no matter how we spun it, our experiences were impacted by comments like “remember the old days when they had that big seafood buffet?” Even though our Christmas in Key West was less festive due to the Great Recession, we were so very thankful and extremely cognizant of how lucky we were to be there under any circumstances in the broken economy.

We had a nice lunch in a half-full dining room and then enjoyed the pool and shore areas while our lunch settled. I made Christmas Greetings calls to family while lounging on the back porch of Casa Marina, all as I watched he old orange biplane go by with tourists on a sightseeing flight, and appreciated watching families frolic in the swimming pools while much of the rest of the country was shoveling snow. It’s a great way to spend Christmas. I highly recommend it!

As for New Years, of course Key West does its own thing there too. The Gay crowd had a big red stiletto shoe that dropped at midnight, and Sloppy Joe’s had a big Conch shell that dropped . . . after all, what else would do in the “The Conch Republic.”

As cruisers, we never make it to anything that happens after nine p.m. it seems. Midnight? Forget it! When the Conch Shell and Red Shoe dropped we were fast asleep on The Moon. We did stay out after dark a few times in Key West, and I bought running lights for the dinghy, but it is a big deal and a LONG run in the dark in the dinghy to the mooring field, often in pretty rough seas. So, we didn't stay out at night very often.

Here's a look at the Christmas Holidays:

As the sun sets, the Holiday lights come on, transforming palms and channel markers into Holiday cheer.

As is customary, the salon of Indigo Moon is lit up and decorated for the Holidays too!

Melissa at Casa Marina for the Christmas Buffet

This year, with the Great Recession and the down economy, the buffet is scaled back and the lines are short . . . but at least we are still in short pants!

Christmas Day on the south shore of Casa Marina: napping after Christmas Dinner in a hammock in 75 degree weather is pretty hard to beat.

After making a “big run” on the luncheon buffet, Buddy catches his breath and calls family to wish them a Merry Christmas and explain how AWESOME it is to be back in the USA for the Holidays.

Buddy’s view while he lounges after lunch.

At Sloppy Joe’s they are all set up to have a huge Conch Shell drop at midnight to celebrate the New Year.

Several blocks down Duval from Sloppy Joe’s is the Bourbon St. Pub and all Male Guest House and it has a different plan: a Huge Red Pump will drop for the New Year.

As mentioned earlier, being somewhere for several months as a cruiser allows you to genuinely get to know places like Key West. It also allows you to enjoy stretches of perfect weather and plan activities accordingly.

For example, one Christmas several years before we ever went cruising, we flew into Key West for a quick, four day respite to enjoy a warm Christmas in the tropics. A bitter cold front blew in right along with us and we spent four days in sweatshirts and jackets and listened to the locals say how “it was eighty-five degrees just yesterday” and how glad they would be when the weather warmed back up. Of course, that would be the day after we flew out. It was too cold to swim, too rough and windy to go boating, and too cold to really enjoy Key West as it should be enjoyed.

When you're a cruiser, you experience one of the most obscene pleasures imaginable: those perfect weather days are all yours, all of them and all the time, and you get the luxury of "befriending" a locale on the days when it is “on its best behavior.”

As cruisers, we could do things like look out across the mooring field from our boat and over the top of Key West and see if a cruise ship was in. If it was perfect shirtsleeve weather and there were no ships in, we knew we had Key West all to ourselves and would head in for a day of exploration.

If there was a cruise ship in and the weather was nice we would head in, but instead of sightseeing and exploring we would do laundry and go grocery shopping and take care of chores.

And if a cold front was coming through and it was cold, windy, rainy, and less than perfect weather, we’d just stay on the boat and wait for better weather. And I never took that for granted. When I would hear those cruise ship horns blasting to announce their departure on a terribly nasty weather day, I always sympathized with the vacationers and how they worked so hard for a week off and got totally shafted on the weather. Melissa and I never took cruising for granted.

All that said, Key West is windy and rough in the winter as the cold fronts keep barreling through. In the summer, the winds go calm and Key West turns into a pressure cooker of sweltering heat and epic afternoon thunderstorms. In between cold fronts in the winter, however, the weather is perfect. Calm seas, temperatures in the low eighties and low humidity. If you are there for even just one those perfect weather interludes, you will fall totally and unconditionally in love with Key West. Be there for several of those perfect weeks over a period of three months in the dead of winter and Key West becomes one of the most alluring places on earth. The hyper-high real estate prices almost start to make sense.

On one of the rare, super-calm days, we took the opportunity to cover a lot of open water around Key West in the dinghy. There are so many VERY shallow areas that are HUGE, one must use extreme care to study up on the charts and go slow if the sun is in your eyes. The skill of gauging the water depth visually by the color of the water is not optional in the Florida Keys. If you do not have those skills and use them at all times, you will be hard aground very quickly in the Keys.

Okay! I’m ready! I’ve looked at all the charts again, it is a flat-calm, warm, and a stunningly perfect day in Key West and we are going on a dinghy tour around Sunset Key, the shallows to the northwest off Mallory Square, and the Bight. Get your hat and sunglasses and let’s go!

A little hard to see against the grass on the bottom, a spotted eagle ray cruises the shallows off Sunset Key

Wow, this is what the western side of Sunset Key looks like; no cruise ship will ever block your view of the Green Flash if you own one of the beauties! All you need is 5.5 MILLION dollars to own one on the beach . . . but don’t worry, they have bargains located on the inland part of the little island for only 1.5 million!

A closer look at a mansion on the west side of Sunset Key: this is easily a 6 to 8 million dollar home and would also serve as a welcoming center for any Hurricane. One has to wonder what costs more: the home or the insurance.

Looking to the north of Sunset Key, I see a HUGE sailing yacht with no mast. So let’s go see what is up with that!

Wow, this thing is chained to a mooring of some sorts, out in the open waters northwest of the Bight and Mallory square.

Whoa, the starboard side is all torn to pieces and there is a huge block chained amidships and a cable is running out the hawse pipe in the rail and down through the block and under the boat.

Hmmm . . . the name of this yacht is Legacy and it is British flagged in Georgetown; also NOTE where we are: in the distance on the horizon far right are cruise ships at the Key West docks and we are a couple of miles out in open water on the fine calm day.

Hooo weee! Look at the cables and blocks on the port side of the yacht; it is clear now: the keel is in danger of falling off and these cables are holding the bottom of the boat together!

We inquired about this vessel after seeing it and found out it's a hurricane damaged yacht that is just hanging around now. It has become, hands down, I am sure the most opulently appointed bum boat in the Keys. A yacht like this has a multimillion dollar interior and one has to wonder how much of it is still intact and how strange it must be to live on a wrecked vessel of that grandeur.

Hey, let’s head to the Bight! As we head in, the waters get choppy . . . not from the wind but from the current. The natural tidal channel that runs between Key West and Sunset Key experiences very swift currents and that cause turbulence at the surface. Even the slightest puff of wind will kick up.

Heading toward the Bight, it’s a very calm day

It gets "slightly shallow" alright! Better be careful!

An old water taxi is moored off Sunset Key

A quick pass by the cruise ship docks: Holy Mackerel! This is what it would look like if Mickey Mouse decided to run over you at sea: this Disney Cruise Ship is in for the day.

Okay, let’s go into the Bight. Two of the main landmarks are the wooden schooners that offer snorkel trips and sunset sails, and Jimmy Buffett’s recording studio.

Standing up in the dinghy and idling around the Bight: schooners in the background

The Liberty Clipper, one of a half dozen sailing ships that cater to the tourists

In the very southwest corner of the Bight, there is a totally unmarked, nondescript building. It has no windows. It has one metal door and one roll up bay door in the back. It has surveillance cameras on its eves. What is it? Is it an FBI post? Maybe it is part of the DEA? It really is weird looking and does not make sense for such a bunker of a building to be in the Bight. What is this building doing talking up the most prime waterfront commercial property in Key West? Well . . . it’s a little recording studio that Jimmy Buffett put together and owns. Yes, all those millions made by Jimmy’s songs and dreams of Margaritaville (aka Key West) made him so wealthy he can park a recording studio on the seawall in the Key West Bight.

That’s a quick look around the waters immediately surrounding Key West. Let’s now turn our attention inland again. If you have read the entire Indigo Moon adventure, you know that we have often spent time visiting graveyards along the way. Cemeteries can say a lot, even though the Dearly Departed have long been silent. It is yet another window into the character and history of a locale.

And the old Key West Cemetery is quite interesting. Located in the middle of the island in the midst of quiet neighborhoods several blocks east of the mayhem on Duval Street, the cemetery is a world away from the hustle and bustle of the tourist and cruise ship scene. The only thing that breaks the serenity is an occasional low flying American Airlines Express coming over like a crop duster from west to east. Just so happens that the airport’s final approach goes right over the cemetery.

There is quite a mixture of very plain old stones and markers and new, opulent ones too.

It is clear than the Freemasons have had quite an organization in Key West throughout the history of the graveyard. A significant number of headstones have Masonic symbols and, of course, the Freemasons have been around a lot longer than Key West or the United States. The Freemasons date back to the late 16th Century.

Also, there is a Jewish, Bnai Zion section of the grave yard. Bnai Zion is one of the oldest Zionist organizations in America, established in 1908, and describes itself as representing Jewish people throughout the world with particular emphasis on new immigrants in the United States.

Those two groups, the Freemasons and the Zionist Jews, are the largest groups represented in the cemetery.

But this is Key West. Perhaps the most interesting group can be dubbed what I have invented a new name for: the “BE”: the Brotherhood of the Eccentric.” I think that it helps Key West “BE” the interesting place it is.

One of the most famously eccentric of the deceased is Betty Pearl Roberts. She was a chronic hypochondriac during her lifetime. But in the end, after all those years, she finally proved her case with a headstone that reads: “I told you I was sick.”

Let’s take a stroll in the Key West cemetery on a sunny, warm, bluebird day in January:

Some of the tombs in Key West are very old and date back prior to 1700’s

Mixed in with ancient graves, some of the new tombs are modern marble mansions set under the swaying palms

This gated mausoleum is for Freemasons only, and a very large number of the markers scattered about the graveyard have prominent Masonic symbols carved into them.

There is also a Bnai Zion section of the cemetery, complete with gated entrance

This old stone of a Freemason now lies loose on a tomb and indicates that James Ogden was born in Charleston, South Carolina in 1813 and died in 1856 and that “he bore a long and painful illness with Christian fortitude, leaving a loving wife and only daughter to lament his loss.”

Those headstones are the kind that hurt your heart; that one in particular left me speculating that, for Mr. Ogden, Key West must have represented a place special enough for him and his family to leave South Carolina in hopes of a better life. And in the 1800’s this move was not a leisurely drive down Highway 1 in a rented convertible. It took guts and effort back then. What was the reason for his move from South Carolina to Key West anyway? Was it business? What was the source of the adventure? What was the long-term terrible suffering? He was only 43. What happened to his wife and daughter? This is all very catastrophic to think about, especially when pondered by a fellow traveler like me who can readily appreciate firsthand the courage and risk that it takes to make big moves in life.

But just when you think your heart can’t take it, and that a cemetery is a terribly painful place, you see another headstone that tells a different story, such as that of Aleida Marie Blanco. Her humble headstone, with hand-painted inscription, transmits a powerful message of love, happiness, and a wonderful life that leaves no room for lament and sorrow.

Aleida Marie Blanco was on this earth from 1928 to 2007. A loving mother of four, she “loved to shower in the rain, loved papaya, sour sop & dancing. Her motto according to the inscription: “Mi Casa es Su Casa.” I am hard pressed to envision a better selection of words to describe a person who was clearly wonderful to be around and obviously blessed.

And just when I was smiling ear to ear and playing movies in my head with Aleida dancing in the evening and surrounded by her loving family around their dinner table, a noise grew louder and louder until I was literally shaken out of my daydreams! Yikes! Here comes a Continental Express right over our heads. And you have to wonder what all the spirits in this cemetery think of that. Day after day, planeloads of tourists in Hawaiian shirts and with their mp3 players blaring Jimmy Buffett into their ears pass over on final approach. I wonder: what does Aleida think of that? I would imagine she likes it and hopes the visitors get to eat the sweetest papaya and get to shower in the warm tropical rain.

Incoming! My daydreams about the former lives of Key West’s deceased are shattered by the beat of the propellers and the whine of the jet engines on a Continental Express turboprop flying right over our heads on final approach.

The graveyard is not limited to just people. There are pets buried here too. Gene and Anne Otto buried several of their pets here, with names like “Sunny” Otto and “Little Boy” Otto.” They obviously loved their pets dearly.

From 1952 to 1970, Anne and Gene Otto enjoyed the company of “Sunny” who was one of their Yorkshire Terriers. Buried next to “Little Boy” yet another of their pets: Sunny’s inscription reads “his beautiful little spirit was a challenge to love.”

Of course, the most famous grave in Key West is that of Betty Pearl Roberts who was an infamous hypochondriac:

The tomb where Key West’s most famous headstone is located

Hypochondriac B. P. (Betty Pearl) Roberts has the last word on her headstone

Not all tributes are graves. Here, a very old tree stands and someone maintains a rudimentary sign to mark its significance.

East Indian Almond Tree, planted in 1918 in memory of Howard Sands who was killed in France in WWI.

And finally, sometimes you laugh and raise the camera to the unexpectedly funny. Here, two of Key West’s wild chickens are unrelenting and determined to remain on this tomb no matter how close I got. I looked around and there are no other chickens in the whole cemetery. Only these chickens defending this grave. The name on the tomb: Curry

Chickens are dancing on the grave of the man named Curry! You just can’t make some of this up!

Another clue to the unbridled eccentricity that abounds in Key West is reflected in the vehicles you see around the city. It’s fun to be immersed in a society that is so artistic and whimsical that they paint artwork on their cars.

Look out! According to the bumper “MAKE WAY FOR EXCITEMENT!”

No need for a back window because in the Conch Republic they “seceeded where others failed” (it is even more hilarious that “seceded” is misspelled)

Perhaps this car belongs to a girl named Shelly?

The car is a real “beater” of a wreck, but the hundreds of beads and shells make it fun

This is a NICE new Toyota and it has already been turned into a Key West mural

Bicycles are the preferred mode of transport in Key West. The island is so compact that any part of it can be easily reached by bicycle. And locals love their bikes!

This one is cool!

This bike is displayed as a work of art. “Captain Outrageous” is a well known local artist who is sought out to paint cars, mopeds, bikes and all modes of transport. This bike is named “Lost in the Sixties” by Captain Outrageous; the Skull and Crossbones says “Pirate Construction” and then goes on to say: “ NO address, NO phone, NO permit . . . What part of NO don’t you understand.” Folks are a “little bit” anti-establishment down here in Key West.

How about this holiday themed tricycle blaring Christmas music and sporting a decked out Christmas Tree?

And then there are the REAL bikes. Motorcycle Clubs of all fashion rumble through Key West. It is a natural milestone for bikers. What easier promotion could be devised: “Hey, let’s get the Hell away from winter and make a run down the Keys to Key West!” It’s a “no brainer.” Check this dude out at the Hog’s Breath Saloon one block off Duval . . . that’s a real bird on his handlebars, it’s the dead of winter, and here he is half-naked and draped over his bike while listening to the live band fifty feet away. It’s Nirvana for bikers.

Whether by car, motorcycle, or bicycle, there is one universal message: “SLOW DOWN this ain’t the mainland”

Of course, it was not all play and no work for us in Key West. The maintenance and work involved in keeping a cruising catamaran in shape requires more work than you can envision, I don’t care how mechanically savvy you think you are. Not only does the overall responsibility outstrip any forecast, the complications of obtaining parts can be a real bitch. It was great to be back in the USA where parts are available and FedEx can have a new part in your hands in a day.

One of the things you fight on a boat is the toilet. Marine toilets are the source of many a tale about epic battles with recalcitrant equipment that fails in the worst situations, resulting in repairs and cleanup that is nasty beyond description.

There are two manually hand-pumped toilets (“heads” in marine terminology) on Indigo Moon and they are the originals. Over the last six years of ownership, I have rebuilt the guest head twice and the owner’s head (the one we use daily) at least eight times. The internal seals and valves are rubber and they wear out. Eventually the pumping function becomes diminished and the entire pumping system needs to be disassembled, cleaned and reassembled with all new parts.

These parts kits can run as high as $125 US in the Third World. A new, complete toilet can run $500 US.

One of my plans upon return to the US was to buy brand new, complete toilets for the boat. AMAZING! While swinging on a mooring off Fleming Key, I was able to pick up a wifi signal. Now online, I was able to locate and buy TWO complete toilets for less than $100 US each (shipping and all). Two days later, the mooring field office called ("you’ve got two big boxes here"). And voila! I have brand new toilets for less than I would have been paid for a tiny bag of rubber rebuild parts in the Third World.

So, one day was dubbed “It’s time for us to get a-head!” and I spent my time going through all the heads’ plumbing systems and replacing the toilets.

Of course, the old toilets had to be brought to shore in the dinghy. This made for a funny opportunity. Not many people have a head in their dinghy! I actually sat on one going into the dinghy dock. That turned some "heads" . . . even in Key West!

Wow! Look at the "Captain's Chair" in that dinghy!

There was another job during our stay that was not so fun. The kitchen faucet’s inner workings finally gave out and it began to leak badly. This was during the time we were severely ill with the Mexican Flu. Temperatures also plummeted while a cold front came through. I had to get in the dinghy for a rough, cold ride to the dinghy dock, walk 45 minutes to the Home Depot, buy a faucet and adapters to try and get it to hook to the French fittings on my European Catamaran, walk 45 minutes back to the dinghy, ride back in the cold and get drenched in the dinghy, hoist the dinghy back up on the davits, and take an hour and a half to make a new faucet work . . . nothing about it fit . . . I had to drill out a larger hole in the sink pedestal and MacGyver all the plumbing connections.

I had the pleasure of doing all this while coughing, sneezing, shivering and running fever. I was so ill that I really just desperately wanted to lie down. But that was not an option. Some of my memories of Key West are not so nice.

Shifting gears back to the tour, we did make it to neighboring Stock Island that lies just across the small bridge over which Highway 1 runs east to the upper Keys and the mainland.

Stock Island has some commercial fishing harbors and docks. Our great friend Ed Watson who lives aboard his boat at Marathon Key came down to see us several times in his car and we would have lunch and go sightseeing.

On one of those visits, Ed showed us around Stock Island.

Buddy and Ed Watson on the fishing fleet docks of Stock Island

The “Gulf Queen” shrimper of Key West is unloading

These are HUGE bags of fresh shrimp

Into a freezer container, off the shrimp go headed for your dinner plate

One of my favorite places in Key West is hanging around the Bight, seeing the boats come and go while eating ice cream or dining at one of the waterfront restaurants like Turtle Krawls. The Bight is the one area where there is a true harbor, bustling with all things nautical. It’s fun to stop and study the rigging and designs of the old wood schooners like the Western Union and others. There is always some live music blowing in the breeze from the open air Schooner Bar, where some Jimmy Buffett wannabe is always on stage singing some anthem about leaving the harsh world behind to become a beach bum in the sun. It’s about as fine a Modern Day Fantasy Pirate’s hangout as one could ever conjure.

One weekend, our dear friends Nick and Thea, from Morgan 41 Out/Island Blue Bonnet, came down from Ft. Lauderdale to visit . . . and deliver boat parts too. Always a sight for sore eyes and lifelong friends made solely from cruising, we really enjoyed seeing them!

Here are some photos:

One of Buddy’s favorite hangouts is the Bight, where all the recreational and charter fleets base their operations.

The Western Union, one of Key West’s most famous wooden ships.

The Jolly Rover is a “fake” galleon of steel, with home port of New Orleans

At Turtle Krawls, there is an upper dining deck that overlooks the entire Bight and according to them “it’s more fun on top.”

The bustling dinghy dock at the Bight. It’s 5 dollars a day, or you can get a month pass for 75 dollars

Nick and Thea, ready to head back to Ft. Lauderdale

When is the last time you saw a huge Blue Marlin wrapped in Christmas lights?

Not directly on the Bight, but only a block inland, “B.O.’s Fish Wagon” serves the best Grouper Sandwich on earth. This small kiosk with open-air dining cranks out a pricey yet irresistible Grouper Sandwich that kept us coming back week after week.

Buddy at B.O.’s Fish Wagon restaurant

The dining room in B.O.’s is wide open and the wild Key West chickens see to it that no one needs to clean the floors

So, what can one do to walk off a big lunch? Well, how about walking down to the South End of the Truman Annex to the Florida Keys Eco-Discovery Center. There is a surprisingly nice facility that includes really first-class exhibits about the Florida Keys, including the eco-system, the location of known shipwrecks, and even a really nice theater that features films about the wildlife of the Keys.

During the film we watched, in one underwater segment, the photographer dove down to inspect the underside of a subsurface grass ledge just off of the mangroves and in the shadows under the ledge it was PACKED with dozens and dozens of HUGE Caribbean Lobster. You could tell who the lobster hunters were in the audience . . . we started howling and jumping up and down like wild baboons . . . I think one guy was about to attack the screen and see if he could yank one of those lobsters right out of there! For all of us who have looked for lobsters under a thousand ledges over the years, it was an AMAZING sight that really got us amped-up.

We spent several hours at the Eco-Discovery Center. It’s a must see in Key West.

Come on in; the Florida Keys Eco-Discovery Center is free

The Center has nice exhibits!

Look out for that spotted eagle ray!

The scores of happy days we spent exploring Key West under the warm topical sun in the winter of 2008-2009 routinely ended with a sunset journey back to The Moon where she swung happily on a mooring in the Garrison Bight Bay. As the cold fronts came and went, and our adventures waxed and waned, each day was, more often than not, graced with dazzling sunsets of orange and purple.

From the decks of Indigo Moon, the sun sets brightly over Fleming Key to our west

In the twilight, the whole mooring field goes pastel-purple this particular evening

And with those fabulous sunsets our adventures in Key West come to a close. We are extremely grateful that we had such a grand opportunity to get to know Key West personally. But for the calendar reminding us that Hurricane Season will be upon us in only a few months, and also the fact that our annual haul-out and maintenance on Indigo Moon must be accomplished, we could have stayed in Key West forever.

But that is the reality of cruising. Seasons bring deadlines to cruising and it was time for us to move. And so, it was with heavy heart and a tearful goodbye that we made ready for sea and our priceless adventures in Key West came to a close.

Where to next? MARATHON! And it will be a fabulous landmark in our cruising adventure where we will close the circle and officially complete our circumnavigation around the entire Caribbean. We have a lot of great cruising adventures, fellowship, and fun ahead of us. So stay tuned. There’s much more to come!

 

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