The Weekender: Key West

Sunshine, fish tacos and even more fish await at the southernmost point of the US. Here’s what to pack for a long weekend in quirky Key West. 


Modern Seaside Living at the Gates Hotel

The Gates, Key West

Roll your streamlined Rimowa suitcase into this hip, new, boutique hotel just off Highway 1, where the only things that top the suites’ sweet minimalist design are the chic poolside cabanas. While there’s no restaurant on-site, the Gates’ resident Blind Pig food truck serves up small bites of “Conch fusion” cuisine to soak up those poolside mojitos or rum runners. 

Make a Pilgrimage to Hemingway’s House

Hemingway House, camera
Novastock/Photolibrary/Getty Images

See what inspired Papa in his natural environment — the pool, his typewriter and the 6-toed cats — at the Ernest Hemingway Home. From the moment you step inside 907 Whitehead St., the furnishings, the taxidermy trophies and even his personal book collection look frozen in time — just like your souvenir Polaroids.

Spend a Full Day Sailing

snorkeling, wetsuit
Stephen Frink/Photographer's Choice/Getty Images

One can’t fully appreciate Key West without exploring the world beneath its beautiful turquoise waters. Experience Key West as the rum runners and pirates once did with Danger Charters, snorkeling through a live reef in your wet suit, kayaking among the mangroves and stopping for a private island picnic.

Ride Along Duval Street

TheCrimsonMonkey/E+/Getty Images

Rent a bike and tool along Duval Street, Key West’s mile-long downtown hub, home to such mainstays as Hemingway’s favorite bar, Sloppy Joe’s. Tucked 1 block off the main drag is Garbo’s Grill, a husband-and-wife-owned food truck that serves renowned mahi-mahi tacos, Korean BBQ and umami burgers.

Enjoy After-Dinner Drinks on the Porch

The Porch, skirt
Nick Doll

This quirky, quaint conch house is what you expect made Key West an artists’ haven in the first place. A floral skirt will seem festive as you sip on one of its impressive array of craft beers or wines on its namesake porch.

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Jessica Menk
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