Key West

< Mallory Square >

Key West is at the southernmost point of the U.S. and the last island in Florida’s archipelago known as the Florida Keys. It’s well-known for fishing, drinking, and having few rules. Key West is about a 3-hour drive south of Miami. There is a small airport on the island, but it’s very expensive to fly to the island. If you’re going to fly, the best way to get to Key West is to fly to Miami or Fort Lauderdale, rent a car, and drive over the famous seven-mile bridge and through the Keys. Another option is to fly to Fort Myers and take the Key West Express four-hour ferry shuttle right into Mallory Square.

< 7 Mile Bridge >
Iimage via Flickr by karlnorling

Famous People of Key West

< Jimmy Buffett >
Jimmy Buffett: Image via

Key West was made popular by Jimmy Buffett, who sings about Captain Tony’s. Jimmy also opened a Margaritaville Cafe on Duval Street. When beach bums, drinkers, and island-lovers think of Key West, they usually think of Jimmy Buffett and Margaritaville. The Village People, Beach Boys, and other artists also sing about Key West.

Famous historic writer Ernest Hemingway fell in love with Key West in the 1930’s and you can visit his old house and sit at the same bar he sat at (Sloppy Joe’s) while he wrote novels.

< Little White House >
Little White House: Image via

Harry Truman also had a house known as the Little White House in Key West where he came to relax and recuperate. The home became a working Presidential Office where important meetings were held, and the Department of Defense came to fruition in one of the house’s rooms.

Oil entrepreneur, hotelier, and railroad magnate Henry Flagler, well-known throughout Florida, built Key West’s tourism and trade business to what it is now. He created the first railroad that connected Key West to the rest of the country in 1912 and is a tourist attraction for visitors to Key West.

Tennessee Williams, known for Pulitzer Prize winning plays Cat on a Hot Tin Roof and A Streetcar Named Desire, wrote drafts while staying at La Concha Hotel in Key West. The only home Williams ever owned was on Duncan Street in Key West, where he lived out his life. One of his plays that was turned into an Academy Award winning movie was even filmed in Key West.

Tourist Attractions of Key West

< Conch Trolley >The Conch Tour Train is a trolley that takes visitors through the island to see the famous historic sites, like Ernest Hemingway’s house, the Truman House, museums, the old Cuban cigar maker’s house, the Southernmost Point, and more. The first train began in 1958 as a dedication to Henry Flagler’s train that connected Key West to the rest of the country. Since then, it has taken over 15 million guests through the streets of Key West.

< Mallory Square performer >
Mallory Square performer at sunset

Mallory Square is the place to be in Key West for shopping, sightseeing, and people watching. Especially during sunset, everything that happens in Key West happens in Mallory Square. Mallory Square is on Key West’s historic waterfront. Visit shops, sip coffee at an outdoor café, grab dinner as the sun sets, or grab a drink at a local bar. The Sunset Celebrations occur every night at sunset where you can watch the red sun sink into the Gulf of Mexico next to magicians, clowns, jugglers, psychics, local musicians, artists, food vendors, and many others for an incredible cultural experience. Mallory Square at sunset is a photographer’s dream!

The Southernmost Point Buoy is a concrete buoy anchored at the southernmost point of Key West and of the continental United States. On the corner of South Street and Whitehead Street, this point marks 90 miles to Cuba. Every visitor to Key West should stop by for a quick picture at the iconic Southernmost Point!

Duval Street is the main shopping street in Key West. You’ll find hotels, restaurants, bars, shops, and everything else on Duval Street. It runs north and south from the Atlantic Ocean to the Gulf of Mexico, ending in Mallory Square. You can’t miss it, and you won’t want to miss it.

History buffs won’t want to miss the Ernest Hemingway House, Harry Truman Little White House, Mel Fisher Maritime Heritage Museum, Key West Lighthouse, old Post Office and Customshouse, USCGC Ingham U.S. Coast Guard vessel and memorial, and the Key West Pirate and Treasure Museum. The Conch Tour will pass by most of these, but if you want to go inside and explore, you’ll have to buy tickets.

Where to Drink

< Captain Tony's >Captain Tony’s Saloon was the site of the original Sloppy Joe’s from 1933 to 1937. It was the famous watering hold of Ernest Hemingway, Jimmy Buffett, Truman Capote, Tennessee Williams, and Shel Silverstein. The original Captain Tony was a larger-than-life character often described as a character right out of an Ernest Hemingway novel. Originally from Elizabeth, New Jersey, he moved to Key West after a run-in with the New Jersey mafia. In Key West, he was a well-known boat captain, gambler, storyteller, and heavy drinker. He started Captain Tony’s Saloon in the old Sloppy Joe’s, which remains a popular tourist fixture with his name.

Captain Tony was a local Key West fisherman, politician, and bar owner. His bar, Captain Tony’s Saloon, still stands today and is a popular tourist attraction. He was a well-known, loved character of Key West, even with his heavy drinking problem. It’s said that at one point, Key West’s mayor had resigned leaving the town with no mayor. The residents of Key West loved Captain Tony so much that they all voted for him as a joke, and became the first drunk, barefoot mayor of Key West. He decided to shave and stop drinking, which lasted a day before he was back in his saloon.

< Sloppy Joe's >The most famous bar in Key West is Sloppy Joe’s, although it’s changed a lot since its humble beginnings. Today, Sloppy Joe’s is on Duval Street close to Mallory Square. It’s a big bar that brings in bands from throughout the country to play for tourists and locals alike. Sloppy Joe’s stays open until 4am and is a Key West tradition.


LGBT Friendly

< Red Stiletto New Year's Ball >Key West has a large gay and bisexual presence, although it’s mostly contained in the southern area of the island. Key West was actually one of the first U.S. cities to openly and actively recruit gay tourists. There are drag shows, gay restaurants and bars, all-male hotels, gay beaches, and gay spas. On New Year’s Eve, a glittery ball drops at midnight on the north end, and a red stiletto heel drops from the gay bars on the south end. Transvestites will stand outside drag shows and entice people to come watch their shows.

There are cabarets, leather bars, clothing-optional bars, and plenty of late-night dancing. If you’re in town with your family, make sure you know which places are safe for children! Gay bars include: La Te Da, Bourbon Street Pub, 801 Bourbon Bar, Aqua Nightclub, Saloon1, Bobby’s Monkey Bar, Garden of Eden, and the Roof Top Terrace at La Concha Hotel.

Peak Season

< Key West Ocean >Key West is a hotspot for New Year’s Eve, spring break (which runs from January 1 through March 31), and Fantasy Fest in October. During these high peak times, hotels are almost impossible to find, so book early.

Between Christmas and New Year’s Eve, vacationers pack into Key West. From New Year’s Day through the end of March, students and vacationers alike flock to the warm weather of Key West. Fantasy Fest is an organized party to stimulate business in the slow season, but has turned into a Mardi Gras-type, clothing optional party. Fantasy Fest includes parades, humorous floats, a Conch King and Queen election, beads, body paint, and lots of drinking. Fantasy Fest draws in over 100,000 people, more than the entire island’s population.

Have you been to Key West? What’s your craziest story from this small drinking island with a fishing problem? Let me know in the comments!

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PS. If you like this post, you might also like Fort Myers Beach and Naples

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