24 Places That Keep the Spirit of Old Florida Alive

From secluded island getaways to raucous dollar-bill bars, these two dozen spots should be on your must-visit list

Photo: Courtesy of the Colony Hotel

Cruising at the Colony Hotel in Palm Beach.

Looking for secret island getaways, swamp sanctuaries, sunken gardens, dive bars, oyster shacks, and other haunts that embody a not-quite-bygone Florida? Here are twenty-four hot spots where you can still enjoy a piece of classic Old Florida. 

Bonnet House
Fort Lauderdale

A block from the seaside strip’s bars and tacky T-shirt shops lies a hidden gem that comes with a bittersweet love story. Chicago lawyer Hugh Birch gave his daughter, Helen, this thirty-five-acre estate, with its tropical gardens and eclectic design, for her wedding to the artist Frederic Clay Bartlett in 1919. She died just six years later, and Bartlett later married Evelyn Fortune Lilly, herself a talented painter. Their whimsical artwork and decor, much of it honoring the couple’s beloved monkeys, remain perfectly preserved.

Cabbage Key Inn and Restaurant

The burger at the Cabbage Key Inn and Restaurant is, like umpteen other places, rumored to have inspired Jimmy Buffett’s “Cheeseburger in Paradise.” Back in the seventies, Buffett drifted to the quiet key and its eponymous establishment by seaplane. Visitors today arrive by boat and can channel the icon with a cold one at the dollar-bill-covered bar, a stay at the inn or one of its surrounding cottages, and of course, a cheeseburger (though don’t expect “french fried potatoes”—the sides on offer are coleslaw and potato salad).

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Cap’s Place Island Restaurant
Lighthouse Point

Opened in 1929 by Eugene Theodore “Cap” Knight, a steamship captain who ran bootleg whiskey in burlap bags from the Bahamas, this seafood dive on the Intracoastal has impeccable Old Florida cred. Behind the bar of the onetime speakeasy and gambling den hangs a wooden figurehead from the bow of a Spanish galleon. The time-warp menu plays the old standards: linguine with clams, crab cakes, hearts of palm salad.

Charles Hosmer Morse Museum of American Art
Winter Park

The artist Louis Comfort Tiffany could coax color and texture from glass, and each December, Winter Park displays nine of his towering stained-glass windows in the central garden downtown. Steps away, the Morse Museum collects the world’s most complete trove of his work, including a chapel that surrounds visitors in mosaics and majestic filtered light. Meditative galleries share vignettes of Tiffany’s ceaseless creativity in the late nineteenth and early twentieth centuries—jewelry, experiments in pottery, and the sketches he drafted before transforming sand into relics.

Courtesy of The Colony Hotel

The Colony Hotel
Palm Beach

Since 1947, the Colony has set the standard for laid-back Palm Beach cool with its dreamy pastels and über-attentive service. For a day in the sun, take a ride on the hotel’s Beach Buggy, a custom-made golf cart with seats decked out in the same fun Seagrape print as its paddleboards. Lounge oceanside on and beneath powder-pink chairs and umbrellas, and if you get hungry, staff will deliver a picnic in a matching cooler.

Corkscrew Swamp Sanctuary

The thirteen thousand acres of undisturbed wilderness in the heart of the Corkscrew watershed provide sanctuary for many of the state’s endangered species, including Florida panthers and roseate spoonbills. Take it all in from the park’s boardwalk, a two-mile trail that ends at the largest old-growth bald cypress forest on the continent.

Cummer Museum of Art

In September 2017, the Cummer Museum’s three formal gardens beside the St. Johns River got a visit from an uninvited guest: Hurricane Irma. The storm swamped the lower tier in four feet of brackish water, uprooted plants, and wiped out electrical, lighting, and irrigation systems. Last June, after a $1.3 million restoration, the revived gardens reopened, their lawns once more green, their reflecting pools once again glassy and pristine: the calm after the storm.

Photo: Courtesy of Florida Southern College

Danforth Chapel at Florida Southern College.

Florida Southern College

Thirteen of Frank Lloyd Wright’s innovative creations grace the west side of this campus in Lakeland, making it the largest single-site collection of the architect’s visionary designs. The impressive structures, some built by Depression-era and postwar students working their way through college, include a chapel that appears to hover above the ground, a first-of-its-kind water dome, a planetarium, and more than a mile of geometric esplanades.

Hole in the Wall Seafood Market and Raw Bar

The shucker wears a ponytail and a camo Ace Hardware ball cap, and if it’s not too busy, he’ll show you a pair of oyster tongs, a miniature replica of the ones they still use in the beds just offshore. Bottles of beer emerge from an ancient green icebox. The waitress is as salty-sweet as the half-shell beauties she delivers by the trayful. (Overheard when the owner lingers to chat up customers instead of giving her a hand: “His jawbone’s got to be sore in the morning.”) Come for the oysters, stay for the unscripted dinner theater.

Photo: Cedric Angeles

Half-shell beauties at Hole in the Wall in Apalachicola.

Honeymoon and Caladesi Islands
West of Dunedin

In 1940, lucky newlyweds won a Life magazine contest to honeymoon in thatched bungalows on a secluded Gulf Coast island, the brainchild of a clever real estate developer who then owned the land. Those lodgings are long gone, but you can still dig your toes into the sand at what is now Honeymoon Island State Park. Bring your pup for a frolic on the pet beach, or for a deeper wilderness experience, catch the ferry to Caladesi Island State Park’s sugar-sand beaches to lounge, or rent a kayak to cruise among the mangroves and seagrass.

Key West’s Bookish Side
Key West

When tickets go live for January’s Key West Literary Seminar, they typically sell out in minutes. That’s partly because the event features best-selling authors, but also because Key West is as alluring to book lovers as it is to party hoppers. That literary draw goes beyond the always-packed Ernest Hemingway Home & Museum: Papa’s in-the-know fans also pop into his apartment building at 314 Simonton Street, where he wrote A Farewell to Arms. (And they’re sure to toast him with a daiquiri at his former haunt Sloppy Joe’s.) Over at Books & Books, visitors who grew up on Are You There God? It’s Me, Margaret delight to discover Judy Blume herself ringing up customers. A couple blocks away, at the Chart Room bar, the novelist Thomas McGuane came to hear an up-and-coming musician named Jimmy Buffett play in the 1970s—and met Buffett’s sister Laurie, now McGuane’s wife. Both McGuane and Buffett have been spotted in the Monroe County Public Library, where archivists will retrieve Tennessee Williams’s faded library card—if you know to ask.

Lorelei Restaurant and Cabana Bar

At mile marker 82 in the Keys, by the beckoning roadside mermaid, you’ll find one of the nation’s premier après-fish watering holes. Famous guides, including Rick Ruoff and Tim Klein, ferry clients directly to the congenial decks of the tiki bar (a former bait shop), where, over cold beer, conch chowder, and live music, they ponder tarpon battles won and lost while watching the sun set lazily over the blue-green water of Florida Bay.

Photo: Dylan + Jeni

Fire dancers spin at Mai-Kai.

Fort Lauderdale

Tiki torches light paths to man-made waterfalls and lush gardens, but at Mai-Kai, the classic kitsch of hula dancers and fire spinners takes center stage at the nation’s longest-running Polynesian dinner show. Drink in the island vibe—waitresses wearing floral bikinis and sarongs serve up punches in ceramic heads—with a splash of prestige. A celebrity favorite in the sixties and seventies, Mai-Kai now resides on the National Register of Historic Places.

Alys Beach

There will always be a place on the Panhandle for mullet tosses and two-dollar Budweisers. But even on the Redneck Riviera there comes a time to put on a clean shirt and splurge on a round or two of “thoughtfully curated,” Instagrammable cocktails. Should the mood strike, NEAT’s sleek tasting room will be ready, amid Alys Beach’s whitewashed villas and art-directed plunge pools. Its rotating menu features cameos by small-batch gins, Japanese whiskeys, and such mixological novelties as turmeric and activated charcoal.

Ole Florida Fly Shop
Boca Raton

Tucked into a nondescript shopping center a few blocks from the Atlantic, Ole Florida Fly Shop serves as the brick-and-mortar mother ship to a massive online store. That enables the shop to carry an enormous selection for walk-in customers. Envision forests of fly rods, walls of fly-tying materials, and concierge-level service that frequently turns a quick stop for a fly or two into an hours-long visit.

Mount Dora

Carry small bills to barter, and scout blue-and-white garden urns and seasoned Wagner and Griswold cast-iron skillets at Renninger’s, the 117-acre flea market and antiques utopia north of Orlando on U.S. 441. Ramble downhill through the outdoor vendors to the air-conditioned heirloom wonderland and find longtime vendor Peggy’s booth for age-softened monogrammed linens and perhaps the same tiny orange juice glasses your mom had when you were a kid.

Rod & Gun Club
Everglades City

Travel to South Florida’s yesteryear at this venerable inn and restaurant. The sprawling complex sits on five waterfront acres at the gateway to the famed Ten Thousand Islands of the Everglades, and has hosted luminaries that include Hemingway and five former presidents. Guests overnight in updated cottages on the grounds, but the original lobby and dining room, lined with square miles of pecky cypress paneling and a Noah’s ark of mounted fish and game, still charm.

Sarasota Art Museum

For a town with a population of less than sixty thousand, Sarasota is surprisingly fertile ground for the arts, with symphony, opera, and ballet productions and a mother lode of midcentury design. “People make pilgrimages from all over the world to see Sarasota architecture,” says Anne-Marie Russell, executive director of a new institution that promises to further raise the Gulf Coast’s arts profile: the Sarasota Art Museum at Ringling College of Art and Design, opening in December. Rotating exhibitions occupy a campus of three buildings, two of them historic schoolhouses that are themselves architectural landmarks.

Stan’s Idle Hour

For one weekend in January, this beach town bursts to life as the dive bar Stan’s Idle Hour hosts the Mullet Festival (this year January 24 to 26). Created in 1985 by the late bar owner and local legend Stan Gober, the event centers on a zany dance contest with elaborate feathered costumes and outlandish choreography, after which one lucky lady is crowned with the coveted title Buzzard Lope Queen. With fresh seafood, live music, and the memory of Gober himself looming large, the festival remains a phenomenon—one that draws as many as five thousand revelers.

Sundy House
Delray Beach

You might think of the Sundy House as a cure for the common hotel: twelve artsy guest rooms behind a 1902 Queen Anne showpiece with a wraparound porch and an airy dining room that serves brunches of national renown. The showstopper, though, is the Taru Garden, a riot of tropical greenery with thousands of plants—coconut palms, ferns, bananas, elephant ears, gingers, bamboo, and plumeria—framing a freshwater swimming pond landscaped to suggest a Yucatán cenote, complete with limestone boulders and waterfalls to explore during your afternoon dip.

Sunken Gardens
St. Petersburg

Decades before Mickey Mouse arrived, tourists drove instead to the west coast to visit Sunken Gardens, one of Florida’s first roadside attractions. A century later, the destination has lost none of its vintage charm in the midst of cosmopolitan St. Petersburg—an oasis chock-full of meandering paths, cultivated lawns, spreading canopies, secret pools and waterfalls, rare flowers, and, of course, its famous pink flamingos.

Photo: Jennifer Kielich

Sponges in Tarpon Springs.

Tarpon Springs
Northwest of Tampa

This city where the Anclote River meets the Gulf of Mexico opens a window to old-world Greece. Divers from the old country came to Tarpon Springs in the early 1900s to harvest sea sponges, and today the Sponge Capital of the World is home to the U.S.’s largest Greek American population per capita (and the biggest Epiphany celebration in the Western Hemisphere). At the docks, catch the aroma of smoked, savory octopus drifting from a nearby restaurant, and overhear locals speaking in their native tongue. If you’re lucky, you may even spot a dive boat returning, piled with a sponge haul.

Three Sisters Springs
Crystal River

When temperatures dip in the winter, manatees flock like snowbirds to Three Sisters Springs on the Gulf Coast, where the clear-as-glass water stays about seventy-three degrees year-round. Don a mask and snorkel to swim alongside the gentle giants mid-November through March, or grab a paddle for kayaking, stand-up paddling, or canoeing. A boardwalk surrounds the springs for an overhead perspective.

Photo: Vlad Kharitonov

A garden at Vizcaya.

Vizcaya Museum and Gardens

Like a scene out of an F. Scott Fitzgerald novel, Vizcaya—once the estate of the millionaire James Deering—surprises with its sculpture-lined driveway, lavish plantings, and juxtaposition of century-old infrastructure, ornate gold accents, and sparkling cerulean water. Pause in the glass skylight courtyard, which lends an ethereal feel to a space that might have played host to Gatsbyesque parties bathed in moonlight not so long ago. 

Susan B. Barnes, Monte Burke, Allison Entrekin, Mike Grudowski, Andrea Guthmann, Sallie Lewis Longoria, CJ Lotz, T. Edwards Nickens, Steph Post, Allison Ramirez, Katherine Rodeghier, Caroline Sanders, and Abigail Tierney