Key West, Fla. takes living on the edge seriously. The two-mile by four-mile island is the southernmost point in the United States (and has the tourist attraction to prove it). When you’re in Key West, you’re closer to Cuba than a Wal-Mart.
It’s easiest to disconnect in a community that seems like a bubble—untroubled by anything happening outside its borders. Key West is where visitors unplug, reset, and enjoy life.
The Gates Hotel Key West is located just five minutes from the Key West International Airport, on the east side of the island. Accommodations take a cue from the surroundings—reclaimed wood, whitewash beams, and creams and neutral tones create a luxurious, beachy feel.
The hotel, part of the Keys Collection, ties into the local flavor by incorporating history, local art, and live music in the design. The walls are adorned with large prints by award-winning local photographer Jorge de la Torriente of De La Gallery.
The Gates’ on-site bar, Rum Row, sits poolside and features an extensive rum list. When sitting at the bar top, don’t forget to look down—the floor is painted with a map of the rum-running route through South Florida. Sip on cocktails made with Key West First Legal Rum Distillery spirits and enjoy a cigar in the Rodriguez Cigar Lounge as night falls.
Though The Gates offers a free shuttle to Mallory Square for hotel guests, the best way to see the island is by bike. Rent a Martone Cycling Co. signature blue bike directly from the concierge and take off for Old Town.
During the day, hit up the historic Ernest Hemmingway House. Take a guided tour of the residence the writer called home for more than 10 years, during the most prolific period in his career. The grounds include the main house, his writing studio, pool, and gardens, all inhabited by more than 50 cats.
For a beach day, bike your way to Fort Zachary Taylor State Park on the west side ($2.50 entrance fee for those on foot or bike). Catch rays on the south-facing strand as you watch boats and jet skis cruise by.
As the sun starts to set, head to Mallory Square for the Sunset Celebration. This nightly street fair showcases performers, artists, and musicians, all celebrating the sunset. Find a spot with a view of Sunset Key, grab some conch fritters or a piece of key lime pie, and enjoy the party.
For a taste of the cigar business, drop by the Rodriguez Cigar Factory, off Fitzpatrick Street. The family behind the business has been in cigar production since 1947, from growing tobacco to rolling it. Today, Rodriguez Cigars is the oldest operating cigar manufacturer in the Florida Keys. Spend some time at the storefront, meet the family, and find your new favorite cigar (the espresso is delicious, too).
While in Old Town, see how rum is made at Key West First Legal Rum Distillery. The distillery is housed in an old Coca-Cola Bottling Facility and features a lineup of 12 different rums.
The first place to look for food in Key West is right outside your hotel room. The Blind Pig, a food truck located at Rum Row, serves a tapas-style selection of regional cuisine, including Cuban, Bahamian, Caribbean, and Floridian flavors. Look for breakfast options like Jake and Bake (Cuban egg press sandwich) and breakfast tacos. For lunch and dinner, sample local fish sandwiches, the Blind Pig (pulled pork, aged cheddar on pretzel bread), and ceviche.
While out and about, drop by the Thirsty Mermaid. The cozy eatery features a full raw bar, a selection of East and West Coast oysters, and ceviche du jour. Grab a seat at the bar and taste some of the craft beer Florida has to offer (look for Funky Buddha and The Waterfront Brewery).
For an upscale night out, make reservations at Café Solé. Come here for classic French dishes and preparations featuring locally caught seafood. Menu options include Duck a L’Orange, Conch Carpaccio, and the can’t-miss Hog Snapper (or hogfish).
After dinner, head to Duval Street. Skip the usual tourist hot spots and head to some hidden gems—The Porch and The Other Side, both located inside the historic Porter Mansion. Enter the home and take a left for craft beer and wine (The Porch) and hang a right for craft cocktails, including a list of absinthes to choose from (The Other Side). Nothing shuts down early here; sip until the early morning hours—the best way to catch a sunrise.