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.

Famous People of Key West

Key West was made popular by Jimmy Buffett, who sings about Caroline Street and Captain Tony’s Saloon. 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.

Harry Truman was a fan of Key West during his presidency in the late 1940’s and early 1950’s. His Key West vacation home is known as the Little White House. It was here that he and his staff 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 tycoon 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

The Conch Tour Train is a trolley that takes visitors through the island to see the famous historic sites, like Ernest Hemingway’s house, museums, 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 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.

The sunset cruises are a great way to spend an evening. They usually start around 6:00 p.m. and end around 8:00 p.m. There are smaller, romantic cruises or big party cruises (the big party cruises are the most fun). They sail back and forth through the gulf side of Key West around other small islands and past private sailboats. It’s a beautiful way to catch a sunset, listen to a live band, snack on hors d’oeuvres, and drink as much free alcohol as you can! Your hotel can sell you tickets and might offer a discount, or buy tickets right at the dock on Greene Street.

Being an island, you’d assume Key West has some great sandy beaches. Surprise: there are actually only three beaches! Fort Zachary Taylor Historic State Park is a popular beach with some grainy sand and trees for shade, but make sure you rent a car or scooter to get to it. It’s on the tip of Key West and there is an entrance fee to get to it. Higgs Beach is a small beach, but it’s the only beach that allows dogs! If you want to play with cuddly best friends in the sand and water, head to Higgs Beach. Smathers Beach is the largest public beach in Key West, about a half mile long. If you’re a true beach bum, this might be your best bet!

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, and you can buy additional tickets to hop on and off the Conch Tour throughout the day.

Harry S. Truman spent lots of time in Key West during his term as President. He used his Little White House as a second home and vacation spot to take the stress away from his staff. You can tour the house with a guide or walk through a few rooms reading plaques and newspaper articles about Truman’s time in the Little White House.

Ernest Hemingway arrived in Key West in 1928 to find the new Ford Roadster that his wealthy uncle had bought for him and had shipped to Key West. Unfortunately, the shipped car was delayed so the dealership insisted he move into an apartment on Simonton Street until the car arrived. While he was stuck here waiting for his car, he continued to write a war story he started en route to Key West. It was during these three weeks he finished the novel, “A Farewell to Arms.” Hemingway grew to love Key West and looked for a more permanent home. After two years, he purchased the home on Whitehead Street. His house is now a museum you can tour for a fee.

Finally, U.S. highway route 1 runs from Maine all the way to Key West. It’s actually the only road you can take if you drive to Key West. You may have seen parts of route 1 in other East Coast states as well. But Key West is one of two places you can see the beginning (or end) of this 2,369 mile road. There are mile markers that mark Mile 0, which is a popular bumper sticker you can buy in souvenir shops around Key West. Don’t forget to get your picture taken at the start of this road that runs up the entire coast of the United States!

Where to Drink

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 inherited Captain Tony’s Saloon in the old Sloppy Joe’s, which remains a popular tourist fixture with his name.

Captain Tony 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 jokingly wrote his name in on the mayor’s ballot…and he won. He became the first drunk, barefoot mayor of Key West. He decided to shave and stop drinking, which lasted for three days before he was back in his saloon with a pint of beer. Luckily, his council was able to run the town until his term was over and a new mayor was elected.

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 bands in from throughout the country to play for tourists and locals alike. Sloppy Joe’s stays open until 4am and is a Key West tradition.

Irish Kevin’s is an authentic Irish pub on Duval Street in Key West. It’s a lively bar with nightly music, plenty of Irish stouts, and some delicious Irish food.

Next up, you’ll run into Fat Tuesday. This is a popular frozen drink chain that looks like an adult 7-11. Alcoholic slushy drinks line the bar; trust the bartender to mix up a few of them for a great swirly concoction!

There is a Hard Rock Cafe and Senor Frog’s nearby on Duval Street, although as chains without much draw to Key West, I never went into either of them. They’re there if you want something familiar, but I recommend one of the unique Key West bars first.

Hog’s Breath Saloon is one of those unique Key West Bars. It’s a popular pub with bar food, cold drinks, and live music. If you want to dance with a can of beer, pop on in! There’s a souvenir and gift shop right in the bar so you can shop for your new favorite shirt on your way out of the bar.

If these changes in latitudes are changing your attitude, Jimmy Buffett’s Margaritaville is a must-stop for any parrothead. Jimmy Buffett’s name is almost synonymous with this little drinking and fishing island and odds are, you’ll be listening to his songs the entire drive down the Keys. Margaritaville has its own line of alcohol to make sure you get the best hurricane or margarita possible. This is also the best place to pop in for a “cheeseburger in paradise.” Just watch out for the sharks that can swim on the land!

The Green Parrot Bar is just off Duval Street on Whitehead Street. It’s the perfect dive with live music and cold beer. The Green Parrot is right across the street from the courthouse so it’s perfect for those who get too rowdy – just a quick walk to the holding cell. It’s also the kind of place you can get too rowdy and probably not end up in jail.

For those looking for an alternative atmosphere, visit Bourbon Street Pub. Outside, you’ll most likely run into some male staff in speedos. Inside, you’ll find some great dance music and the best shots in Key West. You’ll know you’re in the right neighborhood when you pass the the four-way rainbow on the intersection of Duval Street and Petronia Street.

Just across the street from Bourbon Street Pub is 801 Bourbon. Downstairs is a fun bar atmosphere with a stiletto chandelier. Upstairs are nightly drag shows. This was my first time at a drag show and I wasn’t expecting the strip club-like show. Make sure to bring your ones, the dancers expect it! If you want more of a burlesque show that doesn’t involve sticking dollar bills in fake bras, check out the show at La Te Da instead. The Bourbon Street Pub’s show is great for bachelorette parties though, and there are two shows nightly (9:00 and 11:00 p.m.)!

Where to Eat in Key West

Even though Key West is known as a little fishing town with a big drinking problem, there are some great restaurants, especially for fresh seafood. To paraphrase Jimmy Buffett, if you’ve been drunk for over two weeks, passed out and rallied and sprung a few leaks, you gotta stop wishing, gotta go fishing. Being surrounded by water and fish, Key West has some great seafood! In fact, many of the places in Key West have been featured on the Travel Channel or Food Network.

DJ’s Clam Shack is a tiny hole-in-the-wall shack with the BEST lobster roll you’ll ever have. Guy Fieri on the Food Network’s Diners, Drive Ins, and Dives tried and loved the garlic butter clams, but also recommended the lobster roll and conch fritters. I tried the lobster roll and fried clam strips and recommend them both! No fillers, just huge chunks of fish in each. Definitely a place I’d go again and again!

Blue Heaven is open for breakfast, lunch, and dinner, but go for breakfast. Roosters and Hemingway cats run free through the fenced in outside seating begging for scraps. There’s a bar outside and a live band that plays tropical island music. The breakfast is unreal! If it gets too hot, you can also eat inside, but the atmosphere outside is just superb. The restaurant was featured on Food Network’s Food Wars, Rachael Ray – $40 a Day, and Travel Channel’s Man vs. Food Nation. Don’t leave without trying the key lime pie, it’s heaven on earth!

Bad Boy Burrito was not only featured on the Food Network’s Diners, Drive Ins, and Dives but also recommended by the chef at DJ’s Clam Shack. They serve authentic Mexican food and amazing burritos. Guy Fieri loves the Kobe beef burrito and the Cayo Hueso Fish Tacos, but the DJ’s Clam Shack chef loves the vegetarian burrito. I don’t think you can go wrong no matter what you try!

The Food Network’s America’s Best and Travel Channel’s Food Paradise both recommend a trip to Kermit’s Key West Lime Shop for some key lime pie on a stick. I didn’t make it to this stop on my trip but it is a great location, across from the harbor where the sunset cruises sail from and only a few steps from Duval Street. You can’t miss the big green restaurant! If you try the key lime pie at Kermit’s, let me know how it is and I’ll add it to my list for my next trip.

Garbo’s Grill is a food truck in Key West. It’s a little hard to find, but more people have been searching it out since Guy Fieri found it and featured it on Diners, Drive Ins, and Dives. Guy loved the Umamiburger and Korean BBQ Tacos, calling it a “history-making moment in Triple D.” Look for a little hut with some tables out front and a sign pointing to the food truck in the back.

El Meson de Pepe is an authentic Cuban restaurant right on Mallory Square. If you’re looking for some dinner and drinks before or after the sunset festivities, this is a great spot right in the center of all the action. Most of the staff is from Cuba and the food is incredible. Visit Cuba without the hassle of a visa! Try the combos for a little taste of everything.

LGBT Friendly

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, burlesque shows, drag shows, 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 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.

Summer is the low season but Key West is still crowded with tourists. It’s a popular time for families to visit because kids are out of school. However, you’re more likely to find good hotel prices in or around summer. Watch out for hurricanes towards the end of summer though!

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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