Travel Guide: 2 Days on Gasparilla Island

A Sun-Soaked Weekend on Gasparilla Island

Where Old Florida charm meets effortless coastal living

There’s something undeniably timeless about Gasparilla Island — a quiet, car-light barrier island off Florida’s Gulf Coast where days move slower and traditions still matter. We spent a dreamy two days soaking it all in while staying at the iconic Gasparilla Inn & Club, and here’s exactly how we’d recommend doing it.

Day 1: Beach Club Bliss & Island Classics

Morning Coffee + Breakfast

We started the day at The Inn Bakery, grabbing fresh coffee and pastries before the island fully woke up. It’s casual, charming, and the perfect first stop before heading beachside.

Beach Club, Bright & Early

Next stop: the Beach Club at Gasparilla Inn. Pro tip: arrive early to snag your preferred lounge chair by the pool or directly on the beach. From there, it’s pure relaxation — ocean breezes, turquoise water, and not a rush in sight.

Lunch by the Water

Lunch at the Beach Club keeps things easy and breezy. Fresh salads, sandwiches, and island favorites mean you don’t have to leave your sun-soaked spot for long.

Afternoon Tea at The Inn

One of Gasparilla’s most beloved traditions: afternoon tea at The Inn. Served daily, it’s a charming throwback complete with finger sandwiches, sweets, and that signature Old Florida elegance. Pro-tip: Pack your travel Mahjong set to play on the patio during Tea Time! We love the Island Travel Mahjong Tiles from Mahjong House.

Dinner at The Pink Elephant

We wrapped the day with dinner at The Pink Elephant, a Boca Grande institution. Known locally as “The Pink,” this lively spot has been serving guests for decades and is famous for its seafood, creative cocktails, and vibrant island energy.

Day 2: Tennis, Trails & Timeless Dinners

Breakfast on the Island

For breakfast, you can return to The Inn or try The Outlet at The Innlet, a popular local spot loved for its relaxed vibe and classic breakfast fare — perfect fuel for an active morning.

Early Morning Tennis

One of our favorite ways to start the day: tennis at the Inn. Courts fill up quickly, so booking ahead is a must. Morning play keeps things cool (and justifies that extra pastry).

Lunch at a Local Favorite

After tennis, we headed back to The Outlet at The Innlet for a casual lunch — an island staple for sandwiches, salads, and easy midday bites.

Beach Walk at the State Park

Post-lunch, we took a long stroll along Gasparilla Island State Park. With wide, uncrowded beaches and incredible shelling, it’s the perfect place to slow down and soak up the natural beauty.

Happy Hour at BZ’s

Before dinner, we stopped at BZ's for happy hour. This classic Inn lounge is a guest favorite — ideal for cocktails, conversation, and sunset vibes.

Dinner at The Temptation

Our final dinner was at The Temptation, a Boca Grande landmark dating back to the late 1940s. Fun fact: it’s one of the island’s oldest restaurants and known for its old-school supper club feel, fresh seafood, and timeless charm — the perfect way to end the trip.

Why We Love Gasparilla Island

Gasparilla Island is equal parts nostalgic and effortless. From beach club mornings to historic dinners and sunset cocktails, it’s the kind of place that invites you to slow down — and stay a little longer.