If you live in Southwest Florida, you’re not easily tempted by another beach. We live on one of the most desirable coastlines in the country, with calm waters and elegant resorts. But there are things our region doesn’t provide—Atlantic waves, comprehensive butler services, a resort tradition that predates Naples by a generation. For those, you get in the car.We asked three Gulfshore Life insiders who know South Florida and travel it well to make the case for their favorite long weekend. Here are the reservations they opt for when they want to go—not far, not for an extended stay, just long enough for the Gulf to call them back.
High-Gloss History at The Breakers Palm Beach
David Corban has spent his career thinking about how people experience a space, how architecture makes them feel. When the acclaimed Naples architect and Gulfshore Life community advisory board member describes The Breakers Palm Beach, he doesn’t start with pools or the golf course, but with the entrance. “The procession onto the property is consciously done,” he says. “It’s on a monumental scale—you can see it from blocks away, so there is this anticipation entering the site.”
The brick-paved, Florentine fountain–punctuated approach says it all. This is the original language of American resort culture, established in Palm Beach at the turn of the 20th century. Southwest Florida intentionally distilled the formula into an understated form. The Breakers preserves the source material 130 years later.
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Courtesy The Breakers Palm Beach
where swfl spend weekend away breakers palm beach entrance
When Naples architect David Corban describes The Breakers Palm Beach, his mind goes straight to the entrance. “You can see it from blocks away,” he says. The palatial 1896 construction was reimagined in 1925 to mirror Rome’s Villa Medici, with a Florentine fountain at the entry and a 200-foot-long lobby with a vaulted fresco ceiling.
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Courtesy The Breakers Palm Beach
where swfl spend weekend away breakers palm beach dining
Still commanding in its theatrical elegance, The Breakers traces its origins to Henry Flagler in 1896. The resort earned its grande dame status after 1925, when a fire forced a major renovation. Schultze & Weaver—the firm behind Waldorf Astoria New York—designed the facade to evoke Rome’s Villa Medici, constructing a palatial setting to draw the height of Golden Age society: presidents, royalty, the Rockefellers, the Astors, the Vanderbilts.
That legacy resonates beyond the 140-acre oceanfront retreat. A short bike ride leads to Worth Avenue, where in the 1920s, renowned architect Addison Mizner codified the city’s Mediterranean-inflected elegance with a three-story, mixed-use shopping complex—a first for the primarily residential street. Today, the cobblestone streets, arcaded courtyards and Spanish moss of Via Mizner hum with designer boutiques and fine dining establishments that, if only for an afternoon, coax visitors beyond the resort’s storied halls.
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Courtesy The Breakers Palm Beach
where swfl spend weekend away breakers palm beach lobby
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Courtesy The Breakers Palm Beach
where swfl locals spend weekend away breakers palm beach golf course
Set on 140 acres, The Breakers’ storied grounds include one of the state’s oldest golf courses. The Ocean Course was updated in 2018 by Rees Jones, who is among the Southeast’s most respected course architects.
Excursions rarely last long: The Breakers comes with its own culinary prowess. The Seafood Bar—an aquarium-topped bar filled with tropical fish—overlooks the Atlantic waves below. Sunday brunch at The Circle is an occasion, with a raw bar and domestic caviar served beneath a 30-foot domed fresco depicting Italian Renaissance landscapes. At the top of the property, the Flagler Club’s rooms come with a dedicated concierge team and chauffeur service, keeping the formality intact from arrival to departure.
In many ways, Palm Beach is the foil to Southwest Florida—the flash many residents chose to bypass in favor of the Gulf’s restraint. But for a weekend, it’s a visual and cultural feast—especially in the summer, when the crowds thin and the property’s architectural bones are laid bare.
Full-Immersion Luxury at The St. Regis Longboat Key Resort
Gulfshore Life president Jim Schwartzel and his wife, Carly, didn’t plan to stay put all weekend when they left for The St. Regis Longboat Key Resort to celebrate her birthday this past winter. That changed once they experienced the resort’s service. “They’re thinking ahead of you as a guest, almost like they’re reading your mind,” Carly says.
Southwest Florida has no shortage of polished resorts, but even at its most sophisticated, our luxury tends to stay relaxed, residential and familiar. You run into someone at valet, drift into dinner and end up at a table next to people you know. Longboat Key gives you a similar Gulf backdrop—a narrow barrier island, pale sand, wind-ruffled bay—but St. Regis changes the register. You go here when you want the indulgence turned up and the social circuitry turned down.
Courtesy The St. Regis Longboat Key
where swfl locals spend weekend away st regis longboat key bar
Gulfshore Life Jim Schwartzel and his wife, Carly, drive to the St. Regis Longboat Key Resort for unrivaled service along 800 feet of private beach. Sarasota’s arts culture shapes the property’s design. The lobby bar features a circus-cage–inspired installation and art by South Florida muralist William Savarese; drinks are served in Murano glassware inspired by the Ringling family’s winter estate, Ca’ d’Zan, across the bay.
Set on 18 acres with 800 feet of private beach, the resort opened in 2024 on the former site of the Colony Beach & Tennis Resort. The new build marks a clear shift away from the old country club culture, introducing the Gulf to a self-contained destination resort, with all the gloss and five-star service found in the Caribbean or East Coast. The brand’s storied butler program extends to every guest here, regardless of room category, and a separate pool team can be summoned from discreet call buttons at each cabana and lounge chair.
In addition to the main pool, the resort centers around a $14 million courtyard with a waterfall, multiple pools and a winding river system that breaks into smaller enclaves, including a grotto hot tub with a call button that brings Champagne straight to you. Nearby, the 500,000-gallon Under the Sea Lagoon offers aquarist-led snorkeling in a controlled reef environment. Inside, the 20,000-square-foot spa keeps the Gulf in view from the vitality pool, with massage jets and an infinity edge, overlooking the expansive blue.
Courtesy The St. Regis Longboat Key
Courtesy The St. Regis Longboat Key
Courtesy The St. Regis Longboat Key
Courtesy The St. Regis Longboat Key
Imprints from mainland Sarasota, 20 minutes away, keep the glass-clad towers from feeling like placeless, imported luxury. John Ringling chose Sarasota for the winter quarters of Ringling Bros. and Barnum & Bailey. The legacy comes through in the aerialist-inspired rope light fixtures and a maritime-circus print at the Vilebrequin boutique and poolside.
At the theatrical The St. Regis Bar, the brand’s trademark bloody marys are poured into Murano glassware inspired by Ca’ d’Zan, the Ringlings’ winter estate across the bay. Traces of the Colony show up, too. The Monkey Bar returned on its original footprint, now serving elevated beach-stand classics. The balance of play and precision gives the resort its shape.
Unscripted Beach Living at The Moorings Village in Islamorada
Most people know The Moorings Village in Islamorada as the filming location for the Netflix series Bloodline. For Gulfshore Life editor in chief Stephanie Granada, it’s the place with the coconut palms. Before taking the helm here, she spent years as a travel editor chasing singular experiences around the world. More than a decade later, she still remembers the scene. “There must have been hundreds of coconut palms on this expansive stretch of white sand,” she says.
The actual count is 800. Remnants of a former coconut plantation, the palms conceal 18 cottages across 11 acres. You’ll appreciate the instinct: understated, nature-forward, ease over spectacle.
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Courtesy The Moorings Village
where swfl locals spend weekend away moorings islamorada pool
At The Moorings, 18 cottages with wraparound porches provide ready access to the beach, one of the longest sandy stretches among the Keys’ often rocky shores. The crystal-clear water is perfect for snorkeling and fishing.
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Courtesy The Moorings Village
where swfl locals spend weekend away moorings islamorada suite interior
More akin to staying in a beach house than in a hotel, the family-run, 1930s-era property keeps its operations deceptively bare-bones. There’s no beach valet, no clubby pool scene, not even a restaurant on-site. Instead, each standalone cottage comes with a kitchen that staff can discreetly pre-stock with groceries upon request.
Five-star amenities are there if you want them. To dine out, you cross U.S. 1 to Pierre’s Restaurant for a French take on regional bites or Morada Bay’s The Beach Café & Bar for toes-in-the-sand lunches and sunset drinks. A Peloton-stocked fitness center and heated lap pool sit tucked out of sight. Most days, guests stick to bikes, kayaks and paddleboards—or don’t move much at all, alternating between wraparound porches and hammocks.
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Courtesy The Moorings Village
where swfl locals spend weekend away moorings islamorada porch place setting
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Courtesy The Moorings Village
where swfl locals spend weekend away moorings islamorada cottage exterior
The layout prioritizes the tree canopy over blockbuster ocean views, but the Atlantic is always close, offering a distinct departure from the familiar Gulf settings. A short walk from each cottage leads to a beach—one of the few natural sandy stretches in the Keys—and clear-as-glass waters. Snorkelers gain access to the third-largest barrier reef in the world, while flyfishers search for elusive bonefish, and sailfish and marlin test deep-sea anglers. It’s a short distance from the Gulf, but a world away beneath the wake.
A few hours in either direction, the landscape shifts—Naples’ mangrove-lined coast gives way to dense wetlands, then open fields, then island bungalows and stretches of Atlantic beach. Each place runs on its own terms, but the throughline holds. You’re not trading one version of Florida for another so much as moving between them, before settling back into the one you chose.