There’s a classic way of doing Key West. 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 is emerging, 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. A cult classic still sold in gift shops today (now in its eighth edition), 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.”
Digital Access For Only $0.99
For the most comprehensive local coverage, subscribe today.
“You really just can’t beat your daily life here,” Shultz said. “You probably have the best collection of people from all over the place that get along that you could ever have.”
Craft beer bubbles up
Shultz opened The Porch (429 Caroline St., 305-517-6358) in July 2010 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, the property’s large front porch and garden begs to entertain.
“I always wanted to own a bar,” Shultz said. “My grandparents owned a bar. And I felt like something was missing on the island. 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. Savvy tourists soon joined the party, too.
Since then, Shultz, 39, has become an island mogul, following The Porch with 2 Cents restaurant (416 Applerouth Ln., 305-414-8626) in January 2013, The Other Side cocktail bar (also 429 Caroline St.) last May and the forthcoming Waterfront Brewery set to open in the coming weeks at 201 William St., inside the old Waterfront Market at the historic seaport.
“I can’t help myself,” Shultz said with a laugh.
In each new endeavor, the formula has been the same: fill a void on the island and get the locals’ stamp of approval.
A gastropub is born
At 2 Cents, 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 said. “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: nachos with duck confit, chicken wings marinated in sweet chili sauce, brioche grilled cheese with tomato-basil jam and next-level jalapeño poppers wrapped in bacon.
Cocktails over here
The Other Side (305-849-0930) is situated 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 head and original photography by Michael Marrero.
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’ Piña 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.
More beer on the way
Shultz is opening Waterfront Brewery with business partners Joe Walsh and George Esdensen, an ambitious project that has renovated a vacant grocery store.
“It’s a huge, weird space,” Shultz said of what will soon be a 2,500-square-foot tasting room featuring live music on an outdoor deck, as well as two restaurant concepts: fine dining upstairs and a laid-back pub downstairs.
They’ve recruited Justin Stine of Tampa’s Cigar City Brewing as head brewer to create Key West-style craft beers like incorporate Key lime, star fruit, mango and other locally sourced ingredients.
Since December, longtime Key West chef and professional kiteboarder Paul Menta has been distilling rum for his Key West Legal Rum brand.
Located inside an old Coca-Cola bottle factory, Key West Legal Rum is producing seven year-round rum varieties and more than 15 seasonal offshoots. Menta even ages some of his rum in American oak barrels that he soaks in seawater for local flavor.
His distillery and tasting room (105 Simonton St., 305-294-1441) is open to visitors daily.
“We can’t keep Sloppy Joe’s stocked,” Menta says of the high demand for his rum at a popular watering hole and others on the island. New hotels, like The Marker and The Gates, also are 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 culinary and libation movers and shakers is honoring that history.
“I like providing a platform for people to do their talents,” Shultz said, referring to his team of chefs, bartenders and business partners. “They make me look good.”
Shayne Benowitz is Miami.com’s hotels & travel editor. On Twitter @ShayneBenowitz.
Where to stay
The new: The Marker Waterfront Resort, 200 William St., 305-501-5193. Opened in December, it is the first new hotel built on the island since 1994. From $489 a night.
The now: NYAH, 420 Margaret St., 305-296-9259. Short for Not Your Average Hotel, this wallet-friendly guesthouse is tucked behind a charming conch cottage in Old Town. From $40 a person or $359 a night.
The next: The Gates, 3824 N. Roosevelt Blvd., 305-320-0930. This is the first hotel you’ll see when you turn onto the island from U.S. 1, with shuttle service to be provided soon to Old Town. The hotel opened this month. Introductory rates from $249 a night.
The classic: Casa Marina, 1500 Reynolds St., 305-296-3535. Conceived by Henry Flagler, this 311-room Waldorf Astoria property is a South Florida gem. From $449 a night.