GASPARILLA ISLAND: Old Florida, Barefoot and Beautiful

Travel

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If you close your eyes and imagine Florida before the neon and noise — before theme parks and crowds — you might find yourself on Gasparilla Island.

It’s a sliver of sun-kissed coastline tucked between Sarasota and Fort Myers, where the Gulf breeze carries whispers of old fishing tales and the only traffic jams involve golf carts.

Here, mornings start with the smell of salt and fresh pastry. Afternoons dissolve into shell-hunting and sunsets that feel like a benediction. It’s not a party scene — it’s a slow exhale. The kind of place you come to reset your rhythm.

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Where to Stay: The Gasparilla Inn & Club

If Ernest Hemingway, Jackie O, and Jimmy Buffett designed a getaway together, it would look a lot like The Gasparilla Inn & Club — genteel, storied, and casually luxurious.

Step through the white-columned entryway and you’ll feel time ease its grip. The veranda hums with quiet conversation, the kind that pairs well with a mint julep and a sea breeze. Guests drift between the main inn, beach cottages, and the waterfront club like it’s a private world — because it sort of is.

Stay for the impeccable service; linger for the island calm. You’ll play a round on the legendary golf course, sip cocktails at BZ’s, and dine by candlelight at The Pink Elephant — one of Florida’s most charming, wink-and-a-smile kind of restaurants.

If your soul leans more barefoot than bowtie, hop a water taxi to Little Gasparilla Island, where rental cottages perch right on the sand and golf carts are the only way around. No cars, no noise, no pretense — just waves, wind, and wide-open stars.

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7 Unmissable Things to Do on Gasparilla Island

1. Bask at Gasparilla Island State Park – Swim, snorkel, and collect shells at one of the Gulf’s cleanest, calmest beaches.
2. Visit the Port Boca Grande Lighthouse & Museum – Built in 1890, it’s the postcard view you’ll want to keep forever.
3. Charter a Tarpon Fishing Boat – These waters are legendary for “the Silver King” — even if you just watch, it’s a thrill.
4. Bike or Golf-Cart Around Boca Grande – Charming boutiques, ice cream parlors, and pastel homes that could fill a novel.
5. Boat to Cabbage Key – Dine beneath thousands of dollar bills signed by travelers before you; Hemingway would approve.
6. Stroll Historic Banyan Street – Shaded, stately, and straight out of a watercolor painting.
7. Chase the Sunset – From South Beach Bar & Grille, you’ll swear you’ve never seen that many colors in one sky.

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Eat & Drink: From Bright Mornings to Golden Nights

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Daytime & Brunch Vibes

• The Inn’s Beach Club Café – Gulf views and Southern breakfast classics done right.
• The Fishery – Fresh catch, boat access, no fuss — just perfect coastal dining.
• Johnny Leverock’s – Shrimp baskets, key lime pie, and the casual rhythm of locals who’ve earned their slow pace.

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Romantic & After-Dark Magic

• The Pink Elephant – Elegant but playful, with coastal cuisine and martinis that linger on your lips.
• Beach Road Wine Bar & Bistro – Outdoor tables, soft live music, and a wine list worth a toast (or three).
• Cabbage Key – Reachable only by boat — half adventure, half island party.
• BZ’s at the Inn – Where you sip nightcaps in linen and laughter, trading tomorrow’s plans for another round.

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The Passport Life Takeaway

Gasperilla Island isn’t for everyone — and that’s exactly the point.

It’s for the ones who crave quiet over chaos, charm over flash, and sunsets over screens. It’s for the traveler who knows that sometimes the most beautiful journeys happen at half-speed.

So come hungry. Come barefoot. Come ready to rediscover how good life can feel when you trade the noise of the world for the rhythm of the waves.

Because here, on Gasparilla Island, time doesn’t pass — it shimmers.

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