June 1, 2020
Due to travel restrictions, plans are only available with travel dates on or after
Due to travel restrictions, plans are only available with effective start dates on or after
Ahhh, Key West. It’s so much more than Parrot Heads and cruise-ship shoppers; this little island is home to artists and treasure seekers, hippies and outlaws, six-toed cats and wild chickens. The southernmost point in the continental United States, Key West is a lush and free-spirited place that hasn’t lost touch with its history.
You can fly directly into Key West International Airport, but we think a road trip is the best way to approach this fabled destination. It takes about 3 and a half hours — and 42 bridge crossings — to make the scenic drive south from Miami.1
Simply wandering around tops our list of the best things to do in Key West. Stroll down Duval Street to check out the lively bars (and their livelier patrons), shop for souvenirs like hand-rolled cigars and authentic shipwreck coins, and admire the many ornate Victorian buildings. At sunset, head to Mallory Square for nightly shows by acrobats, sword-swallowers and other street performers.
The Ernest Hemingway Home and Museum is a must-see for any fan of the great American author. Knowledgeable guides share little-known Hemingway lore, and more than 40 cats — some descended from Hemingway’s six-toed pet — roam the property.
Ernest Hemingway’s Home and Museum
Despite Key West’s Caribbean feel, the island’s not known for great beaches. Because it’s protected by a barrier reef, waves are minimal and beaches are mostly manmade stretches of sand. Nevertheless, you can stretch out in the sun at Fort Zachary Taylor beach. The sand is pebbly and the bottom rocky, but this beach has clear water that’s perfect for swimming and snorkeling.
Anglers won’t want to waste much time on land; charter a boat to enjoy Key West’s legendary fishing. In the bay between Key West and the mainland, you’ll find bonefish, tarpon, permit, redfish and snook; out in the Atlantic, you can tackle marlin, sailfish and swordfish.2
Finally, adventurous travelers should take a seaplane or boat to Dry Tortugas National Park, 70 miles west of Key West. This little-visited park consists of seven islands and a 19th-century fort. Camp, kayak, snorkel the pristine reefs or dive shipwrecks.
For the full Key West experience, seek out a quaint and cozy lodge or B&B. One favorite is La Mer House & Dewey House, sister properties in the Southernmost Beach Resort. Fling open your balcony doors to enjoy the ocean view, and start your day with a chef-made breakfast on the terrace.
Key West Harbor Inn is a three-story mansion in Key West’s Old Town that offers quiet seclusion just blocks from Duval Street. “Play Naughty. Sleep Saintly,” is the motto of The Saint Hotel Key West, a playful, modern hotel with a private pool.
Hotels and nightlife along the promenade during a winter sunset
Looking for luxury? You’ll have every wish granted at the Sunset Key Cottages, a collection of island villas reached by a 7-minute boat ride from Key West. A breakfast basket’s delivered to your porch each morning, and a private, palm-lined beach awaits.
Key West cuisine is full of tropical flavors: conch and coconut, crab and, of course, Key lime. Taste them all at Louie’s Backyard, a fine-dining favorite known for conch chowder, grilled tuna, and Gulf-caught shrimp and grits. Another of the best Key West restaurants is Blue Heaven, a casual spot where chickens scratch in the yard and the Key lime pie is made fresh daily.
While the food is fine in Key West, the drinks are legendary. Sloppy Joe’s, which opened in 1933, serves Hemingway’s favorite libation, the Papa Dobles (Bacardi light rum, grapefruit juice, grenadine, a splash of sweet & sour, club soda and fresh-squeezed lime). The Schooner Wharf Bar’s known for its frozen Rum Runner.
The famous Sloppy Joe’s at night
Shake off your winter blues by hopping down to Key West for a week. Just don’t forget your sunscreen — or your travel insurance. A robust travel insurance plan from Allianz Global Assistance can protect you in case of covered medical emergencies, trip cancellation/interruption, travel delays and more. Travel happy!