Perched at the very tip of the Florida Keys, Key West is a small island packed with things to do. Not many secrets exist on an island this size, but locals know a few—including just how to spend a perfect day in the Conch Republic.
Bow to the Queen: Start your day with Cuban coffee and cheese toast ordered through a window at Cuban Coffee Queen in the Historic Seaport. Snap a selfie by the mural on the wall so your friends have no doubt you are in the southernmost city.
Walk the Wharf: The best place to watch the island wake up is on a walk along the Historic Seaport. Start behind Cuban Coffee Queen and wind past historic Turtle Kraals restaurant, then follow the boardwalk along the water to Front Street. Tall ships, fishing skiffs, and snorkel tour boats prepare for their day on the water, as shop keeps get ready to open their doors.
Books and Buffett: Key West is a literary town. Pick up some local beach reads at Key West Island Books on Fleming Street. Local ghost stories, bucket lists, books about roosters, and advice for quitting your job and moving to Key West line the shelves. The place is a Key West institution. Across the street, you can stock up on water and sunscreen at Fausto’s Food Palace. Jimmy Buffett used to buy his chocolate milk here after a night on the town. He even wrote about it in one of his songs.
Run the Rum: Take a quick tour of Key West’s First Legal Rum Distillery and grab a bottle or two for a taste of Key West when you return home. The flavors are creative and all of the rum is prepared by chefs in their Simonton Street distillery.
Fritter Away: No trip to Key West is complete without trying some conch fritters. Some of the island’s finest are served at the Southernmost Beach Cafe on the Atlantic end of Duval Street, right by the ocean where playwright Tennessee Williams liked to swim. The entire menu is good, but trust us on the conch fritters.
Bike the Other Main Street: Duval Street gets all the fame, but neighboring Whitehead Street makes a strong argument for being the best street in Key West. Rent a bike and start at the famous Southernmost Point Monument. Continue northwest, toward the Gulf of Mexico, and you will pass the lighthouse, Ernest Hemingway’s home, the courthouse, an amazing kapok tree, some of the largest banyan trees on the island, the Audubon House, the Mel Fisher Maritime Museum, and more. Stop at the locations that float your boat, or just cruise by and admire them from the street.
Pie on the Fly: It would be criminal to visit Key West and not indulge in some key lime pie. Head to the Key West Key Lime Pie Company on Greene Street and see what all the fuss is about. Try a traditional slice or one dipped in chocolate and served on a stick.
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Hang With Your Piers: A stroll down Higgs Beach will take you past historic West Martello Tower and the African Refugee Cemetery to a place where locals like to gather when the sun goes down. Stretching out into the Atlantic Ocean, the Edward B. Knight White Street Pier—affectionately referred to as the unfinished bridge to Cuba—is a favorite of birds, dogs, and humans all year long, even though the sun can only be seen touching the water here in winter months.
Sangria and Tapas: Before your trip, make reservations at Santiago’s Bodega for the island’s best tapas. Located deep in the heart of Bahama Village, the restaurant gets its name from the main character in Hemingway’s The Old Man and the Sea. Come for the sparkling sangria. Stay for the yellowfin tuna ceviche and the beef tenderloin.
Crawl Off Duval: At night, venture off packed Duval Street for a locals-approved bar crawl. Start with a craft cocktail and a round of pool at General Horseplay on Caroline Street. Next, head to Shots & Giggles on Ann Street for a dose of local color and one of their 60 craft beers. Head for the Chart Room Bar, tucked away in the Pier House hotel, for cocktails where Buffett played his first Key West gig and treasure hunter Mel Fisher plotted his search for the Atocha. Resist the urge to fill up on the free peanuts, popcorn, and hot dogs. The best live music in town can be found at the Green Parrot Bar, which touts itself as a “sunny place for shady people.” Locals and tourists alike spill out of the bar and dance on the sidewalks of Whitehead Street until late. Catch a set and then duck around the corner to Mary Ellen’s Bar on Appelrouth Lane for a silly dance party with the regulars.