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.

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.

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.)

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.

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.

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.)