Your Weekend Escape Guide to Key West

PSA: TripAdvisor just named Key West the number-one city to visit this year. What better excuse to plan a trip to this chain of islands off the tip of Florida? Colorful pastel-painted beach houses, swaying palms, Ernest Hemingway’s historic home and the rowdy bars of Duval Street—we’re there. Here’s how to spend a weekend eating, drinking and lounging in gorgeous Key West. 

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Make A Quick Pit Stop In Marathon

From Miami, reaching Key West takes just under four hours. Halfway through the trip, make a quick stop in Marathon to stretch your legs. Grab a bite at Sparky’s Landing, a seafood and cocktail joint known for mahi-mahi sandwiches and Bloody Marias, a Key West take on the classic Bloody Mary. If you have some extra time, spend an evening at Tranquility Bay, a waterside resort complete with a private beach, fishing, water sports and a romantic oceanfront restaurant.

Unwind In Stock Island

For the best of both the beach and the city, book a room at Oceans Edge, located in Key West’s Stock Island neighborhood. It’s one of Key West’s newest and largest luxury properties (rates start at $175), featuring 360-degree waterfront views, six (!) glistening pools, complimentary paddle boarding and kayaking, and an open-air waterside restaurant and bar. (If Oceans Edge is booked, keep an eye out for the charming Sunset Key Cottages or the Pier House Resort & Spa, which is just a few blocks from Old Town.)

Be A Little Bit Touristy In Old Town

Channel your inner travel blogger and stroll through Key West’s pastel-colored streets in Old Town. For history, visit the Ernest Hemingway Home, where the revered author lived and wrote for more than a decade. (About 40 cats still live there!) Then, tour the Truman Little White House, the winter White House of President Harry S. Truman. You’ll also want to take a trip to Civil War-era Fort Zachary Taylor and climb the Key West Lighthouse. Oh, and don’t forget to roam the town’s bustling Duval Street, a mile-long stretch filled with stores, restaurants and bars.

Eat Like A Local

Seafood and key limes reign supreme in Key West. Blue Heaven is an absolute must for brunch. (Order the shrimp Benedict and a slice of key lime pie.) For lunch, head to Eaton Street Seafood Market or Fisherman’s Café for the freshest seafood on the island. Make sure to visit Old Town Bakery for one of the tastiest (and tartest) key lime pies. Other favorites include Louie’s Backyard for Caribbean American and Seven Fish, a swanky seafood bistro.

Drink Like Hemingway

No weekend in Key West would be complete without exploring the city’s eclectic nightlife. Start with sunset cocktails at Sunset Tiki Bar and Grille and enjoy the tropical music and panoramic views. After dinner, head to Sloppy Joe’s (one of Ernest Hemingway’s favorites) or Caroline’s Other Side, a snazzy watering hole known for its innovative rum- and gin-based cocktails. (We’ll take the New Old Fashioned blended with bourbon, orange and cherry, please.) We also love Pepe’s Café, a wood-paneled dive bar that dates back to the early 1900s.

Catch The Sunset In Mallory Square

Every evening, locals and visitors gather at Mallory Square two hours before the sun descends into the Gulf of Mexico for an evening festival filled with music, food and performance. Where the party goes after that is up to you. (Um, you might even end up catching the sunrise.)

Take One Last Detour

Right before you hit the Seven Mile Bridge on your trip home, make a stop at Bahia Honda. This beachside park—covering more than 500 acres and with a view of an abandoned historic bridge—is perfect for a day of snorkeling, kayaking, tanning (with SPF) and boating before you head north. We suggest waking up early to give yourself three to four hours of sun and surf before driving home.

clarissa buch

Miami Editor

Clarissa Buch Zilberman is a writer and editor based in Miami. Focused on food, lifestyle, and travel, her work has appeared in Food & Wine, Travel + Leisure, Bon Appétit, and...