If you’re looking to trade the winter slush for a dose of "barefoot luxury," there is no better time to put Sarasota on your 2026 travel map. While Florida is full of sunshine, Sarasota offers a rare "vintage-meets-modern" energy—a place where you can spend your morning in a world-class gallery and your afternoon kayaking through mangroves or walking the iconic Ringling Bridge.
According to Brian Hersh, CEO of the Arts and Cultural Alliance of Sarasota County, the region is currently hitting a remarkable cultural high. "Sarasota offers this incredible duality—small-town charm with big-city amenities," Hersh explains. Winfred van Workum, General Manager ofThe St. Regis Longboat Key Resort, agrees that the area defines refined relaxation. "Sarasota defines barefoot luxury," van Workum says. "It delivers a refined yet relaxed sense of luxury that today’s discerning travelers seek."
In 2026, Sarasota is celebrating a wave of 100th anniversaries, including the historic Sarasota Opera House, the legendary Ca' d'Zan (the Ringling mansion) and Art Center Sarasota. As Hersh puts it: "It's like watching a century's worth of cultural investment come into focus all at once... some people are just now discovering what's always been here, kind of like vinyl making a comeback." The city is celebrating with a "Centennial Season" of special concerts and exhibitions that make every block feel like a piece of living history. Here is your insider guide to the best of Sarasota this spring:
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Where to Stay: Seaplanes and Circus Chic
View this post on InstagramSarasota’s hotel scene is leaning into its unique heritage with a sophisticated flair, offering everything from high-design boutiques to ultra-luxury beachfront escapes.
The St. Regis Longboat Key Resort: For those seeking the ultimate arrival, you can now "arrive by seaplane directly into Sarasota Bay" via a partnership with Tropic Ocean Airways. Once on property, you can explore a 500,000-gallon saltwater lagoon where marine biologists are currently introducing new spotted eagle rays.Cirque St. Armands Beachside: This new standout on Lido Key blends "circus-town charm with real elegance." The design is a whimsical mix of Art Deco and Big Top—think ostrich feather chandeliers and pinstriped columns.The Ritz-Carlton, Sarasota: For the classic standard of excellence, you can't beat the Ritz, which is celebrating 25 years in the city. Van Workum notes that "what really sets it apart is access to the Beach Club," allowing guests to toggle between downtown energy and private Gulf-side lounging.While the city is famous for Siesta Key Beach, locals often gravitate toward Lido Beach or the "quiet, unspoiled backdrop" of Longboat Key Beach. For a deeper immersion in nature, Hersh recommends a kayak tour through the mangroves or a visit to The Bay Park. If you’re feeling adventurous, head south to Venice’s Caspersen Beach to hunt for prehistoric shark teeth. At the St. Regis, guests can even snorkel and explore thousands of marine creatures with its Under the Sea Lagoon experience, getting up close with stingrays and puffer fish. Of course, no trip is complete without a stop at Marie Selby Botanical Gardens, which van Workum calls "absolutely astounding."
Where to Eat: Hyperlocal and Award-Winning
Sarasota’s dining scene is currently defined by creativity and quality. Indigenous is the "must-book" spot for award-winning, hyperlocal sustainable seafood, while Baker and Wife is a favorite for showcasing the region’s creative culinary talent. Inside the St. Regis, CW Prime has recently debuted a new menu under head chef Drew Adams, who van Workum says has brought "such a charismatic, elevated approach to the restaurant." For a classic Sarasota experience outside the resorts, Michael’s on East has undergone beautiful recent renovations, and Veronica’s in South Side Village remains the go-to for an "elusive date-night."
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Can’t-Miss Shops and Stops
For the best browsing, head to the historic Palm Avenue to explore its legendary galleries, or wander through St. Armands Circle to visit boutiques like The Met. If you’re looking for a hidden gem, Hersh recommends 502 Gallery in Burns Court, which champions local creators. For a stylish souvenir, stop by the Vilebrequin boutique at the St. Regis to snag their bespoke, circus-inspired print. Before you head home, grab a morning bite at Bread Bandits—Hersh is a "loyalist through and through"—or visit Le Shop in St. Armands for a sophisticated coffee break.
Related: These 5 ‘Analog’ Florida Towns Are Trending for Spring Break 2026
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