Visitors flock to the Florida Keys for the laid-back vibe, rum cocktails and golden sunsets over the Gulf of Mexico. And while each key has its very own personality, the most frequented isle is the very last one in the chain, Key West, where you’ll find lively Duval Street, bustling Mallory Square and the home of Ernest Hemingway. Here are a few more of the very best things to see and do in quirky, cool Key West.
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Photo courtesy of Sharael Kolberg
Best place to drink in some macabre Key West history
Contending for title of “oldest bar in Key West,” Captain Tony’s Saloon is a colorful place with a rich past. In former incarnations, it served as a morgue and you can still see a gravestone next to the pool table, as well as the hanging tree that grows right through the bar. After that, it served as a bordello, gambling hot spot, telegraph office, cigar factory and gay bar. In perfect dive bar fashion, the ceiling is strewn with dangling bras and dollar bills. Truman Capote, Jimmy Buffett and Shel Silverstein, among other famous characters, have all raised a glass here.
Best place to do whiskey pickle shots
Green Parrot Bar is the oldest bar in Key West, but it’s still hopping. With rocking live music heard from the sidewalk, this iconic saloon is a respite for people from all walks of life who want to enjoy the lively side of Key West.
Best place to spot a Hemingway look alike
Sloppy Joe’s is a must-do when visiting Key West. As a favorite watering hole of Hemingway, the bar hosts an annual Papa (Hemingway’s nickname) look-alike contest. The large stage hosts phenomenal bands and the bartenders make a mean “Sloppy Rita.”
Best place to get key lime pie on a stick
In Key West you can get key lime taffy, daiquiris, cookies, fudge, peanuts, French toast … and, of course, pie. What’s even better is key lime pie covered in chocolate … on a stick. Heaven. You’ll find that and a variety of other key lime indulgences at Kermit’s Key West Key Lime Shoppe. Visit the Elizabeth Street location — they have more things to taste.
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Best place to bunk with your buddies without breaking the bank
At adult-only Not Your Average Hotel (NYAH), friends can share a room without worrying about splitting the bill. The Build Your Own Room model allows guests to sleep up to six per room, with each guest paying for their own bed, which comes with a locker to store your stuff. While there, take advantage of the free Wi-Fi, Starbucks coffee and continental breakfast.
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Best place for a taste of locally-made rum
Ernest Hemingway liked to write, go deep sea fishing, enjoy the company of women and, of course, drink fine rum. Hemingway Rum Company pays tribute to Hemingway with Papa’s Pilar dark and blonde rums crafted on property at the Key West distillery. Pilar was the name of Hemingway’s beloved boat, and also the inspiration for his famed novel The Old Man and the Sea.
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Best place to search for manatees
A trip to Key West wouldn’t be complete without exploring the waterways. Lazy Dog Charters offers a tranquil two-hour guided kayak or SUP exploration through the lush mangroves in search of marine life, such as sharks, rays, sea stars and (fingers crossed) the elusive manatee. The best part? The kayaking dogs that accompany the tour guides. Not a bad dog’s life.
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Best place for a sunset sail
It doesn’t get much better than mixing wine tasting, sunset and sailing. Climb aboard for a Danger Charters “Wind & Wine” sailing experience and be pampered with a variety of fine wines, beers and hors d’oeuvres while watching the sun set over the southernmost tip of the Keys. The attentive staff caters to guests’ needs while seamlessly tending to the 65-foot schooner as it glides through the open water. A great way to end the day.
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Best place to spot island ghosts
Looking for something spooky to do while visiting Key West? Act like a real-life ghostbuster on Sloan’s Key West Ghost Hunt. Visit favorite spots the spirits of the afterlife frequent and use techy tools to listen to them and ID their whereabouts. You’ll also hear the local history of those who have passed and end the walk with a “cleanse” to make sure none of them tailgate you home.
Best place to catch a sublime sunset while watching someone juggle fire (on a unicycle)
The Key West Sunset Celebration is held nightly at Mallory Square. Street entertainers gather to awe guests with a variety of talents that include sword swallowing, tight rope walking, balloon art, dog tricks and more. The festivities also include a variety of live music and food vendors, but the main attraction is the magnificent sunset.
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Best place to spot a polydactyl
This former Hemingway residence is now a museum with guided tours that tell of his adventurous life in Key West. Sure, seeing his writing studio where he scribed some of his famous novels is great, but the real stars are the six-toed cats (called polydactyls) who freely roam the estate. We’re not talking a couple of house cats here. On last count there were nearly 50 of them living on the property, all carefully cross-bred descendants of the original polydactyl cat who was a gift to Hemingway, an avid fisherman. The six-toed cats were considered to be good luck for seamen, and so Hemingway kept dozens of them around.
Photo courtesy of Sharael Kolberg
Best place for a classic selfie
You can’t leave Key West without a selfie in front of the landmark that designates the Southernmost Point of the continental United States, located only 90 miles from Cuba. Get there early: The line to snap a shot can be long.
Best place for a beach day with a side of Civil War history
The Fort Zachary Taylor Historic State Park is home to one of the Keys’ best beaches, but you’ll also find the park’s namesake Civil War-era fort here, which dates back to 1845.
Sharael Kolberg
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Great overview of key places.