Key West – America’s Caribbean Island

I have vacationed in Key West FL for as long as I have lived here in the sunshine state. I moved down to Florida in 1986 and quickly discovered America’s Caribbean island. The island is just 90 miles from Cuba and is steeped in history. There is only a few ways to get to Key West. You can fly there (yes they have their own international airport, you can drive there, take a boat, or a cruise ship stop over, or take a high-speed ferry from Ft Myers or Marco Island Florida. Back in the early 1900s the Flagler railroad took you there but that train line was wiped out by a huge hurricane in the was a train that took you there on the  I have always drove because I enjoy the scenic drive over the keys from the tip of mainland Florida to the end of US 1 in Key West.

The island is small, just 2 miles wide by 4 miles long and it is surrounded by the most pristine aqua blue water both on the gulf of Mexico and the Atlantic ocean.  For the millions of tourists this is a party and relaxation destination with ample hotels, time shares, and quaint bed and breakfast establishments. If you like bar hopping you will find it difficult to hit every bar on the small island even in a weeks stay, as there are well over 300 of them nestled in the island. Of course drinking and revelry is only one of the many attractions – fishing is huge and you can find everything from huge fishing excursion boats to small private vessels that will fill your fishing itch. Jet Skiing and nature tours are also quite popular in addition to just strolling or bicycling around the island to take in the rich history.

The history of of the island goes back to the early 1500’s when Juan Ponce de Leon visited the island in 1521. The Name Key West is actually derived from the Spanish phrase Cayo Hueso (kajo weso). It translates into bone cay which is a low island. It got this name because it was supposedly littered with the bones  of the native inhabitants. Being such a small island there was little space to bury the dead. Great owned the island in the mid 1700’s from 1783 to 1783 when the Spanish took it back. The island was actually not officially under any nations control for years. In 1822 Lt. Commander, Matthew C. Perry, sailed to Key West and planted the U.S. flag, claiming the Keys as United States property. It is claimed that no one protested and there for therefore the United States of America laid claim to the island and it became property of the US.

The island was actually a Union Strong hold during the civil war even though the state of Florida was a confederate state.  The main union Fort is now a national park – Fort Zachary Taylor and the two other forts – East and West Martello Towers, are now museums that are open to the public.

There are many other historical sites that one can visit, such as the Little White House which was President Truman’s sanctuary away from Washington DC. He spent a significant number of days of his presidency on the island. You can also visit the Hemingway House that was Ernest Hemingway’s residence on the island and to this day you can still see the 6 toed cats that are descendants of Hemingway’s cats. Another piece of history is Bahama Village that is nestled just east of the Little White House. This sector of the island is where native Bahamians also known as “Conchs” settled on the island. Many of the structures here are houses that were taken apart piece by piece and moved from the Bahamas to Key West and reconstructed. The village has some wonderful dining establishments and unique gift shops.

One of the great stories about the island is the creation of the Conch Republic. In 1982, the US Government set up blockades on US 1 to inspect vehicles coming out of the Florida Keys. They were looking for illegal immigrants from Cuba as a result of the Mariel Boatlift. The blockade caused a massive traffic jam and caused tourism to drop significantly. The city of Key West took action and decided to secede from the US and declare the island as the nation of the Conch Republic.  Thia did not last long, as the message was heard loud and clear and the blockade was ended. Every year on April 23rd the island celebrates Conch Republic day.

Beyond the history of the island, there is also the incredibly colorful sunsets that can be seen each evening down at the west side of the island on Mallory Pier. Key West is not a morning town, it is a night town, and nothing represents this more than the festivities of watching the sunset each night. You can watch street performers including musicians, magicians and illusionists each night as the sun rests for the day, over the Gulf of Mexico. It is then, after the sunset, that the fun begins on the island. Locals and tourists alike pour out onto Duval street and the bars start to pulse with music. Duval street is the main entertainment strip on the island with such famous  establishments as Sloppy Joe’s, The Bull, Rick’s, Dirty Harry’s , and the Hogs Breath Saloon

Stroll with us and we will take you on a pictorial Cigar and Bar tour of Key West. You can start on either end of Duval  Street (East or West). We will start on the west end. First stop for this would be the Rodriguez Cigar Factory to grab some sticks for the stroll. But save a little cash to pick up an additional stick or tow at some of the other shops on the crawl. Rodriguez Cigars  is off of Duval in the west end section at 113 Fitzpatrick Street.

Now after leaving Rodriguez you want to walk north on Greene Street and walk into Capt Tony’s. This is the original Sloppy Joe’s from back in the 1930’s. Note the tree that is growing out of the building in front of the bar. The building dates back to 1851 when it was an ice house and doubled as a morgue. It was the watering hole for many a famous gent from Ernest Hemingway, Truman Capote, Jimmy Buffett and Tennessee Williams. And yea that tree was there back then.

After leaving Capt Tony’s head up Green street to the entrance of the Hogs Breath Saloon. This is one of many Iconic Key West bars. I suggest you buy a t-shirt here. It is by far just the coolest Key West Shirt to bring home.

Now walk out of the Saloon at the Duval Street exit and walk across the Duval to Sloppy Joe’s. This is one of the most popular destinations on the island and features some awesome drinks and entertainment on their big stage. Smoking is not allowed in Sloppy Joes but you can stand outside and still catch the action.


Walking east on Duval you will come across the heart of the night life area with famous watering holes like Durty Harry’s, Kevin’s Irish Pub, The Hard Rock, Ricks, Fat Tuesday and more. By this time you may be a little hungry and in need of a another cigar, So first get some pizza at the islands best pizza – Angelina’s  right next to Durty Harry’s.


If you need another cigar and did nto buy enough at Rodriguez Cigars you can always pick up another at the local Island Cigar vendors on the strip or stop into the

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By this time you should be in front the world-famous “The Bull” bar which is across the street from Fat Tuesday’s and the old white church. The Bull is one of my favorite watering holes on the island. It is a three-story establishment with live performers on the street level bar, a second floor bar walled the Whistle Stop, and the roof top clothing optional bar  called the Garden of Eden. The second floor Whistle stop is a nice place to hang out  and sit on the outdoor balcony and watch the people down on Duval.



Of course if you need to ever get your drink on more, when the night crawls into day you can always stop in the Lost Weekend Liquor store and pick up a bottle. It is just around the corner from The Bull. This is another cool place to pick up a t-shirt.


A few other attraction along Duval is the once famous Strand Movie Theater which is now a Walgreen’s and the Old White Church.  Both are steeped in history and worth a visit. Of course yo will have to put that stogie somewhere when you enter.


Continuing east on Duval you will come across the LBGT section of bars and clubs. These can be fun places if you want to see a drag show or just mingle with the crowds. Taking Duval all the way to the end you will reach South Street and the Southernmost Hotel. Turn right and head to the end and you will come to the famed Southernmost Point of the United States. Just 90 miles to Cuba.


After taking some photo ops there, and then  head back west on Whitehead street and you will com across one of the hidden gems of the island – The Green Parrot Bar. It is a locals hangout and has some of the best drink prices on the island. It was the original offices of Pan Am airlines. Sadly they do not allow cigar smoking in side but like all good Key West bars you can always stand outside and still watch the awesome bands that they have every night.


After mingling with the locals continue down Whitehead and you will come across the Ernest Hemingway House. Closed at night but still a wonderful site to see.

We happened to be in town during the Christmas holidays and that just added a little extra to the scene. The buildings, homes and Bed and Breakfast houses were decorated in glittery lights. Here are some of the sights that the Island had to offer.

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