Dining and Unwinding in Key West

Seven square miles of free-spirited fun trailing off the tip of Florida, Key West is calling our name. We’re answering with five Kimpton hotels under one collection as Kimpton Key West, fanning out across the heart of historic Old Town.

Dine and shop on the vibrant and historic Duval Street. Image Credit: iStock.

While we’re in “coming soon” mode, discover a few reasons Key West beguiles us. From bar-hopping off the beaten path to island-hopping off the coast, laid-back travelers will feel right at home here.

Open since 1933, Sloppy Joes’s offers live music and dancing for locals and visitors alike. Image Credit: iStock.

Drink Locally

Imbibing has become an art form in Key West, and certain establishments have put this tiny island on the map. There’s Sloppy Joe’s, an institution since the day after Prohibition was repealed in 1933. And Green Parrot Bar, hosting poetry slams and tattoo contests since 1890.

Reserve some time for out-of-the-way gems, too. Like the small, charming Virgilio’s Martini Bar, home of stellar martinis and live music nightly. Sip a Belgian Sunburn IPA or a Key Lime Gose at The Waterfront Brewery, known for Key West’s highest deck. Chase down charcuterie and cheese with organic and small-batch wines at Viv Wine Bistro. And at General Horseplay, a speakeasy-style bar, laugh out loud as you choose among sexy cocktails like the Crime of Passion: made with pisco, passion fruit liqueur, lemon and….glitter.

Green Parrot Bar has been serving Key West since 1890. Courtesy of Green Parrot Bar.

Explore Aquatically

The world’s third largest coral reef is off the coast of Key West, making this an oceanic oasis for water activities. If you’ve never seen wild dolphins in their natural habitat, a dolphin safari will inspire wonder and awe. Kick back on a secluded sand bar or relax on a sunset cruise with a custom charter boat trip. For the ultimate H2O excursion, charter a seaplane to Dry Tortugas, one of North America’s most remote national parks, where you can snorkel the living reef and roam Fort Jefferson, the largest brick building in the western hemisphere.

Charter a plane for an aerial view with Key West Seaplane Adventures. Images Courtesy of Key West Seaplane Adventures.

Roam Tropically

 With palm trees and lush foliage everywhere you look, Key West is equally alluring by land. Here are some can’t-miss mentions for first-time visitors:

• Mallory Square — Where sunsets are celebrated nightly with buskers and street performers.
• Southernmost Point — The concrete buoy no self-respecting selfie-lover can resist.
• Ernest Hemingway Home & Museum — See the famous author’s home, gorgeous gardens and the many descendants of his six-toed cat.
• Duval Street — A mile-long stretch of all-day happy hour lined with Bahamian and Spanish architectural beauties.

Once the famous author’s Key West residence, the Ernest Hemingway Home and Museum is now a historical landmark. Image Credit: iStock.

Graze Endlessly

Greet the day at our favorite local coffee roaster, Cuban Coffee Queen, and sink your teeth into a “sunrise special”—half a Key Wester sandwich (eggs, cheese, choice of meat on pressed Cuban bread) and a steaming cafe con leche.

The swanky-cozy Little Pearl wows the palate with day-boat fresh catches like sautéed local snapper and diver scallops. Tucked several blocks away from the bustle of Duval Street is El Siboney, a favorite hole-in-the-wall Cuban restaurant. Try the classic sliced roast pork with a side of sweet plantains or fried yuca. If we could eat all three meals at the mural-laden Moondog Cafe & Bakery, we’d order breakfast tacos (with chimichurri) by morning, lobster salad for lunch and Key West fisherman’s bowl (six types of seafood!) for dinner. At Blue Heaven, go for the eggs benedict with lime hollandaise, black-bean bowl for lunch, and Jamaican jerk chicken for dinner.

Sweets deserve their own paragraph. Our top picks include Blue Heaven’s key lime pie (with merengue piled up to your chin), Flamingo Crossing’s homemade ice cream with local tropical flavors, and Better Than Sex, a sultry dessert spot with offerings like Cookie Nookie Pie and Peanut Butter Perversion.

When in Key West, indulge in a slice of key lime pie. Image Credit: iStock.

Land Comfortably

Once you’ve taken in all the Key West you can handle, Kimpton Key West welcomes you with your choice of five hotels—each with its own storied background and bohemian ambience to suit whatever mood you’re in.

—Katy Davis