If ever a postcard for Old Florida made it into the 21st century, it would be of this thinnest of islands parked on the shimmering Gulf of Mexico between Fort Myers and Sarasota. But Gasparilla is more complex than the visuals. Atop a local population that loves its playground setting (and seven miles of sugar-sand beaches), the seasons bring in a diverse group of wealthy industrialists fleeing the frigid North, tarpon-obsessed fishermen, and maritime pleasure cruisers in boats of all styles and sizes. The little village of Boca Grande is the epicenter of Gasparilla life, with pastel cottages and palm-lined streets, nary a stoplight, and low-key preppy attitude.
Gasparilla Island by the Numbers
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Average July high: 92
Average January low: 52
Median home price: $1,268,500
Average commute time: 22 minutes
Number of sunny days: 266
Best Beaches and Other Attractions
The nine miles of sand that line Cayo Costa State Park are a gorgeous getaway, and reachable only by ferry or private boat. On-island, locals love to raft up when the sandbar (it has no other name) by the causeway emerges from the water at low tide.
The Boca Grande Bike Path runs the length of Gasparilla Island on an old rail bed, a six-mile ribbon of asphalt that makes for a great self-guided tour as well as a non-motorized way to get around. Beach access from the path is a breeze. Don’t miss the insanely photogenic Port Boca Grande Lighthouse and Museum, and then dally among upscale shops and restaurants around the former Boca Grande Railroad Depot.
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Where to Eat and Drink
The patio at the Pink Elephant (locals just call it “the Pink”) is a nice place to nosh on a salad, flatbreads, or a fish sandwich alongside the Boca Grande Bayou. PJ’s Seagrille sounds and looks like a seafood shack, but steps it up with a basil-tomato crab bisque and artistically presented grouper and red snapper plates.
Where to Stay
Don’t let the scurvy pirate on the sign fool you: the stately and stylish Gasparilla Inn and Club oozes Old Florida elegance (mind the evening dress code). Cottages have parlors as well as lanais, and there are three croquet lawns (world championships have been held here) along with a Pete Dye-designed golf course, tennis, and a beach club that includes the resort’s spa, plus a pool and restaurant.