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Great Escapes // Key West

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Ocean Key Resort & Spa
Ride your bike past Ernest Hemingway’s one-time home en route to the Southernmost Point. Stroll through galleries filled with colorful paintings and hand-thrown pottery crafted by local artists. Dine at award-winning restaurants, and shop for eclectic home accessories. Sip a cool cocktail under the stars, or take in a top-tier theatrical performance or a reading by a world-class author. Frankly, this is not the Key West of your spring break of yore.
Key West wall mural by New York artist MOMO
Begin your island adventure with an invigorating session of yoga on the beach at Fort Zachary Taylor State Park or perhaps spinning, Pilates or boot camp courtesy of Stay Fit Studio. After you’ve worked up an appetite, stop at local favorite Camille’s: As you take in the eclectic mix of sculptures, prints and paintings by home-grown talents, sample the eggs Benedict loaded with Key West lobster. After breakfast, get out and explore. Perhaps the best way to see the sights is on Lloyd’s Tropical Bike Tour. One of the island’s most colorful characters, Lloyd will lead you on a leisurely two-hour bike tour of the island, machete in hand, ready to offer samples of mango or coconut plucked straight from the tree.
Ernest Hemingway Home & Museum
The less athletically inclined can hop on the famed Conch Tour Train that zips around the island. En route, you’ll learn about the Audubon House & Tropical Gardens, where John James Audubon painted the local bird life, and the Ernest Hemingway Home & Museum (pictured), where Hemingway wrote A Farewell to Arms and descendents of his six-toed cat still roam the property decades after Papa’s demise.
Besame Mucho boutique
After your island tour, hit the upper Duval Street area, aka shopping central. Start your retail tour at Gallery Key West, which carries intricately carved pottery by fifth-generation Key West native Grace Calleja and other works by local artisans. Head up Petronia Street about a block and a half to Besame Mucho (pictured) for vintage-inspired jewelry, much-needed Kiehl’s sunscreen and fragrant Santa Maria Novella soaps.
Archeo Gallery
Back on Duval, stop for lunch at the chic Blackfin Bistro and sample the refreshingly crisp cucumber-shrimp sandwich. From there, wander up Duval to Archeo Gallery (pictured) for bold-colored African art, handmade Iranian rugs and Indonesian village furniture.
Mallory Square
After shopping, settle in at the Afterdeck Bar at Louie’s Backyard for a potent sundowner, the Island Cosmo (made with homemade pineapple-infused vodka). Yes, Mallory Square, pictured, (at the opposite end of the island) features cats that jump through fire at the nightly, carnival-like sunset celebration, but Louie’s is where the locals (natives, known as “Conchs,” and northern transplants alike) gather to toast the setting sun.
Hot Tin Roof

For dinner, sample Louie’s fresh catch of the day or venture further afield to the James Beard award-winning Nine One Five, for colorful tapas; the sophisticated local haven Café Marquesa, for roast rack of lamb with goat cheese and a walnut-mint crust; or Hot Tin Roof (pictured), which specializes in seafood dishes, including truffle-dusted diver scallops, paired with stellar views.

After dinner, take in a documentary at the Tropic Cinema, catch a play with a cast of former Broadway performers at The Red Barn Theatre or relax on the porch of the Grand Vin wine bar as you take in the terrific people-watching. If you do want to sample some spring break-like bacchanalia, the bars on lower Duval Street—Sloppy Joe’s, Hog’s Breath Saloon or the always-open Green Parrot Bar—might be the perfect spots at which to wrap up your perfect day in paradise.

Where to Stay

Where to Stay: Sprinkled throughout the island are numerous bed and breakfasts, as well as larger resorts such as Southernmost on the Beach and the Waldorf Astoria Collection’s recently revamped Casa Marina. The best of the bunch is the paradisiacal Ocean Key Resort & Spa (pictured). Here, you’ll find waterfront views of Key West harbor, private pools and bar areas, relaxing spa treatments at SpaTerre, fishing charters and numerous water sports.

Insider Tip: Some of the best food in Key West can be found in Laundromats and gas stations. Hit Sandy’s Café at the M&M Laundry for a Cuban mix sandwich or Dion’s Quick Mart at the Citgo gas station for crispy fried chicken.

This article has been adapted from the original, which ran in the May 2010 issue of Sky.


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