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Key West: America's Hottest New Luxury Destination for 2015

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Arguably no other destination in America exudes the exotic, off-the-grid allure of Key West in the Florida Keys. Since its discovery in 1513 by Ponce de León, who claimed the island, along with the rest of Florida, for Spain, it's been revered for its wildly independent spirit, devil-may-care vibe, and spectacularly storied history. For a period in the mid-19th century the so-called Conch Republic was the richest city per capita in the United States, thanks to a brisk salvaging business done by savvy local entrepreneurs who plundered the cargo ships that regularly foundered on the treacherous reefs just a few miles from Key West’s shores. Cigar-making was a hot ticket for a time in the late 19th century, and in the 1920s, Prohibition gave rise to another cottage industry in Key West and the surrounding keys, as enterprising locals smuggled contraband beer and rum from Cuba and whiskey and scotch from the British Isles via Nassau. Marijuana smuggling in the 1960s through the early 1980s also made many Key West residents rich (and sent many others to jail).

These days, Key West’s various stints as a carefree capital of vice form the foundation of a booming tourism business that’s the island’s number-one industry, contributing an estimated $1.6 billion to Florida’s economy last year (compared to $2.7 billion for the Keys as a whole). Its reputation as a haven for boozy revelers “wasting away again in Margaritaville,” as local hero Jimmy Buffett famously sings, long eclipsed its lure as a destination for luxury travelers. But that’s all changing now: as the Keys continue to emerge as one of the most sought-after destinations on the planet, sophisticated travelers are increasingly flocking to Key West in droves. Tourist visits to the Keys are climbing by 6% annually, making it one of the hottest resort markets in the country. And in turn, Key West is upping its game.

Where to Stay

The debut of The Marker, a 96-room boutique hotel that opened its doors in December 2014, is a bellwether of this shift. Situated on two lushly landscaped acres on the waterfront in the historic seaport, the property—the first new hotel build in the Old Town district in 20 years—is a resort-like escape smack in the center of the action, with a fresh, contemporary twist. It’s owned by Northwood Investors, which also counts the New York Palace Hotel and The London in West Hollywood among its properties. (I was a guest of the hotel on its opening weekend.)

The Marker’s airy, tropically inspired rooms are designed to bring the outdoors in, offering views of the gardens, the property’s three sparkling pools, or the marina. They’re appointed with blue and white accents, balconies and a thoughtfully curated collection of local art and amenities like bath products from Key West Aloe, founded locally more than 40 years ago and now the largest purveyor of aloe-vera-based products in the world.

The hotel’s pool scene lends a buzzy bit of Vegas-like chic to the hotel, in the best sense: the main complex boasts two pools and plenty of chaises adjacent to the poolside bar (try the prickly pear margarita) and the hotel restaurant, Cero Bodega, which serves up tasty Mexican-inspired cuisine. A separate adults-only pool is a quiet enclave perfect for a snooze or kicking back with a good book.

What to Do, Where to Go & What to Drink

The Marker boasts some unique partnerships, namely one with the Key West First Legal Rum Distillery, the market's—you guessed it!—first legal rum distillery located minutes from the property. The hotel serves its exclusive private-label rum and offers guided tours, cooking classes, and tastings for guests. Another, with Fury Water Adventures, offers a range of aquatic excursions for the active visitor, including a 90-minute, 28-mile jet ski tour around the island. While not for the faint of heart—the tour kicks off with a rather intimidating warning to yield to the fishing boats, cruise ships, and various other maritime vessels with which you’ll be sharing the high seas—it quickly becomes an exhilarating, can’t-miss adventure after a few deep breaths and some serious self-affirmation (“I can DO this!” over and over, grasping the handle bars in a white-knuckled death grip). Whizzing along single-file in your guide’s "bubble trail" (100 yards apart at a minimum), you’ll zoom through the Gulf of Mexico to see the mangrove-fronted islands that Ponce de León’s crew named “Los Martires”—the martyrs—some five centuries ago, then back toward the Atlantic with a pit stop at a tranquil sand bar, and finally past Key West’s Southernmost Point buoy, from which it’s just 90 miles to Cuba.

As reward for making it back to land alive, you’ll want to seek out the perfect spot to take in the singularly spectacular Key West sunset and swill a well-deserved drink. While the Afterdeck at Louie’s Backyard—Key West’s most famous culinary destination—has rightfully been drawing crowds for decades, the sunset cruise aboard the Schooner Hindu is tough to top.

Docked just a few minutes’ walk from The Marker and built in 1925, it’s the oldest, most historic wooden schooner in the Keys. Having fallen into disrepair after decades spent sailing as far as India (where she acquired her current name), the Hindu was purchased in 2012 by William Rowan, a historical renovation architect, who masterfully restored the boat to her former formidable glory. Now captained by his son Josh, a boat systems designer and builder, the Hindu hosts a daily two-hour sunset sojourn, complete with wine & cheese, a friendly crew (led by the inimitably charming Little John) and breathtaking views of the blazing, magenta-streaked horizon. It’s a truly enchanting sail that Ernest Hemingway, Key West’s most famous onetime resident, would have waxed rhapsodic about.

Ashore once again, it’s time for…well, more drinks. Cocktailing has always been central to the Key West lifestyle, to put it diplomatically, and The Other Side, a stylish and refreshingly unpretentious craft cocktail bar, has elevated the island’s drinking scene. Located in the historic Porter mansion a short walk from the hotel, it serves up a range of intriguing concoctions that pack a wallop, including the Great Golden Baby (Nolet's Reserve Gin, Dolin Blanc, and peach bitters), which will set you back a cool $200, thanks to the gin's reputation as one of the rarest ever created (there are plenty of other offerings in the $10-$14 range). Owned by charismatic man-about-town Chris Shultz, a local entrepreneur and co-author of Quit Your Job and Move to Key West, it’s an atmospheric spot to kick off a rollicking evening on the town.

If you're up and at 'em (or just still up) the next morning, make a beeline to 2¢ Restaurant for weekend brunch. Tucked away just off Duval Street, this sister restaurant to The Other Side serves up scrumptious, sophisticated comfort food in the shade of a colossal banyan tree. The house Bloody Mary, accompanied by a maple-glazed-bacon donut hole, will knock your hat in the creek in true hair-of-the-dog style, while dishes like a fried oyster omelette and churro donuts with café con leche whipped cream will quickly quell your hangover.

For more information on Key West and the Florida Keys, visit fla-keys.com.

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