There's a classic way of doing Key West, Fla. It involves dinner at Louie's Backyard, drinks and live music at Sloppy Joe's, photo ops at the Southernmost Buoy, a stop at the Hemingway House, spotting Key West chickens and sunset at Mallory Square. And, of course, plenty of key lime pie, conch fritters and margaritas.
But a younger, hipper Key West has emerged thanks to a few longtime locals turned entrepreneurs and restaurateurs who are shaping the culture of the island and swiftly solidifying new classics.
Chris Shultz, originally from Minneapolis, moved to Key West in 1999 after college in Boston and a stint in Los Angeles. In 2003, he co-authored the book "Quit Your Job & Move to Key West" (now in its eighth edition). A cult classic still sold in gift shops today, it's a comedic take on the magnetic draw of this bohemian, anything-goes island mixed with a dose of practical advice that's tempted many a daydreaming tourist.
And that's how many locals' stories go: "I came here on vacation, fell in love with the place, and never left."
"You really just can't beat your daily life here," says Shultz. "You probably have the best collection of people from all over the place that get along that you could ever have."
CRAFT BEER ON THE PORCH
In July 2010, after a decade as a writer, publisher and irreverent tastemaker (after all, he threw the first TuTu Tuesday party during October's Fantasy Fest in 2009, now one of the locals' most anticipated events), Shultz opened his first brick and mortar establishment, The Porch (429 Caroline St.; 305-517-6358), with business partner Keith St. Peter. A bar dedicated to craft beers and fine wines inside a historic sea foam green Victorian mansion overlooking Duval Street, the property's large front porch and garden beg to entertain.
"I always wanted to own a bar. My grandparents owned a bar," says Shultz. "And I felt like something was missing on the island. There wasn't really a place with a focus on good beer, good wine, good music and a good atmosphere. We wanted to make a place that we liked to hang out in."
With 18 beers rotating through the taps, 50 more in bottles and about 40 wines, The Porch became an instant hit catering to an eclectic mix of locals from fishermen to performance artists to off-duty bartenders who swing by to snag a spot on the porch, sip on suds and watch the tourists stream by. And soon, savvy tourists joined the party, too.
Since then, Shultz, 39, has become an island mogul, following up The Porch with 2 Cents restaurant in January 2013, The Other Side cocktail bar in May 2014 and the forthcoming Waterfront Brewery set to open April 2015 inside the old Waterfront Market at the historic seaport.
"I can't help myself," he laughs.
In each new endeavor, the formula has been the same: fill a void on the island and get the local's stamp of approval.
A GASTROPUB IS BORN
At 2 Cents (416 Appelrouth Ln.; 305-414-8626), a creative gastropub with steampunk light fixtures and intergalactic mural art, tucked away on a quiet lane off Duval, Shultz and St. Peter partnered with Chris Otten, chef-owner of the popular organic burrito stand Bad Boy Burrito.
"We wanted to do pub fare at an elevated level," Shultz says. "It's high end food in a comfortable place where we try to use the freshest, highest grade, best ingredients possible."
The menu is modern and constantly changing, executed by chef de cuisine Brad Schwing. Influences range from Spanish tapas to Southern comfort, featuring fresh caught fish and local ingredients in a mix and match of small and large plates. Think playful yet gourmet spins on classic bar food, such as nachos with duck confit, chicken wings marinated in sweet chili sauce, brioche grilled cheese with tomato-basil jam and next-level jalapeno poppers wrapped in bacon.
A PROPER COCKTAIL BAR
The Other Side (429 Caroline St.; 305-849-0930) was the next project to launch. The name is fitting as it's located on the other side of The Porch in the same historic building. You enter a grand foyer where on one side, a door opens to the sudsy conviviality of The Porch and on the other side, a door leads to, well, The Other Side, a refined cocktail bar with a speakeasy-library vibe decorated with tufted leather chairs, a mounted jackalope's head and original photography by Michael Marrero.
The beauty is, no matter what your party is in the mood for beer, cocktails, wine you can head to either bar and then meet outside to drink together on the porch.
Under the guidance of head bartender Tim Rabior, The Other Side is Key West's first bar truly devoted to classic and creative cocktailing with attention to spirits, fresh fruit and herbs. Classics range from a Hemingway Daiquiri to Champagne Cocktail No. 2, and creative concoctions include the Smokin' Pina made with Cutty Sark Scotch, grilled pineapple, basil and sugar. There's a different featured cocktail every night or you can tell the bartender what you like and he'll whip up something special just for you.
CRAFT BREWERY ON THE HORIZON
Along with business partners Joe Walsh and George Esdensen, Shultz is opening the long-awaited Waterfront Brewery (201 William St.). Located in the iconic, and enormous, Waterfront Market covered in a Wyland mural, The Waterfront Brewery is one of the island's most ambitious projects to date.
"It's a huge weird space," Shultz says of the former grocery store that's stood vacant for the last five years. The brewery will feature a 2,500 square-foot tasting room featuring live music on an outdoor deck, as well as two restaurant concepts: fine dining upstairs and laidback pub downstairs.
They've recruited Justin Stine of Tampa's Cigar City Brewing as head brewer to create Key West micro-suds such as the Crazy Lady Honey Blonde and Key Lime Witness using honey, key lime, star fruit and mango among other locally sourced ingredients.
LEGAL RUM RUNNING
Craft beer isn't the only locally distilled libation in town. In December 2014, Paul Menta, longtime chef, professional kiteboarder and former owner of the still popular Cuban Coffee Queen and Amigo's Tortilla Bar, went out on a limb to create the island's first legal rum distillery inside an old Coca-Cola bottle factory. With seven year-round rum varieties, 16 seasonal and some aged inside an American oak barrel, soaked in the ocean for salty local flavor, the distillery and tasting room is open to visitors daily.
Key West Legal Rum (105 Simonton St.; 305-294-1441) is served at bars throughout the island. "We can't keep Sloppy Joe's stocked," Menta says of the high demand. New hotels, such as The Marker and The Gates, are also putting his rum front and center in welcome cocktails and bar menus.
Key West has remained an attractive destination over the years because of its people, a free-spirited and creative crew. And this new class of movers and shakers is honoring that history. "I like providing a platform for people to do their talents," Shultz says, referring to his team of chefs, bartenders and business partners. "They make me look good." And the whole island is better off because of it.
WHERE TO STAY IN KEY WEST
The Marker Waterfront Resort A stone's throw from the historic seaport and in the heart of Old Town, The Marker hotel opened in December 2014 as the first new hotel built in Key West since 1994. Owner Pritam Singh, the developer behind Truman Annex and the Key West Golf Club, has taken great care to ensure that The Marker blends seamlessly into its tropical, historic surroundings. With 96 guest rooms, a courtyard pool and Cero Bodega restaurant, it embodies Old Key West in new lux digs. From $489 per night. 200 William St.; 305-501-5193.
NYAH Short for Not Your Average Hotel, this wallet-friendly guesthouse is tucked away behind a charming conch cottage in Old Town. Perfect for those traveling in large groups, each of NYAH's 36 unique rooms can accommodate up to six people comfortably thanks to flexible configurations. The rooms are bare bones and clean, while also offering a courtyard pool, complimentary continental breakfast and happy hour in a setting that couldn't be more Key West. From $40 per person or $359 per night. 420 Margaret St.; 305-296-9259.
The Gates Appropriately named The Gates, this is the first hotel to greet you once you turn onto the island from US 1. The New Town hotel opened April 2015. While it's a 15-minute hike to the attractions of Old Town, shuttle service will soon be provided to guests. They're aiming to create a destination resort with island-chic rooms, a pool, cigar bar, food truck and weekly parties courting locals. Opening rates from $249 per night. 3824 N. Roosevelt Blvd.; 305-320-0930.
Casa Marina Conceived by oil tycoon Henry Flagler, who built the Overseas Railroad originally connecting Key West to mainland Florida, the 311-room Casa Marina, A Waldorf Astoria Resort is a historic South Florida gem. The lavish Mediterranean Revival property situated on the Atlantic Ocean is fully updated with an elegant poolscape, private beach and waterfront dining. From $449 per night. 1500 Reynolds St.; 305-296-3535.
(Shayne Benowitz is Miami.com's hotels and travel editor. Follow her on Twitter @ShayneBenowitz.)
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