Start from 21 curated places around Boca Grande, FL, then choose the recommendations that fit your guests.
Restaurants & cafés
The Pink Elephant
The bi-level bayou-side restaurant and pub at the edge of the Gasparilla Inn grounds is where islanders and regulars end up regardless of occasion. The downstairs pub has a bar facing the water; the upstairs dining room is quieter and leans toward fresh seafood and regional cuisine. The outdoor patio faces the Bayou, which makes it the place for a long Tuesday-afternoon lunch in the sun.
The Temptation Restaurant
The oldest restaurant still running on the island dates to 1947, and the main dining room's rustic murals of early Boca Grande life still set the supper-club tone even after the 2024 storms pushed three feet of water through the place. Grilled pompano is the standard-bearer, and the seafood is sourced locally when the season cooperates. The Caribbean Room in back and the wine bar offer quieter alternatives to the livelier front rooms.
Trails & outdoors
Boca Grande Rail Trail
The paved multi-use path runs 6.5 miles along the former Charlotte Harbor and Northern Railway corridor from the north end of the island to the lighthouse at the south tip. It passes through the historic downtown, under the Banyan Street canopy, past the train depot, and along stretches of open bayou and beach access before reaching Gasparilla Island State Park. On a rented bike or golf cart it is the best single thing to do on the island.
Gasparilla Island State Park Beach Walk
The beach walk through the southern state park stretches 1.5 miles along the Gulf between the Sandspur and Seawall parking areas, with no development behind it and shell collecting that gets better the farther south you go. Five distinct parking areas give you the choice of starting points, each with slightly different dune and beach character. The Range Light and Sea Grape sections have the safest swimming; the stretch south of the Seawall runs closer to the Pass current.
Things to do
Tarpon Fishing Charter — Boca Grande Pass
Booking a half- or full-day tarpon charter through one of the licensed guides who fish the Pass and Charlotte Harbor is the defining experience of a Boca Grande trip. Local guides grew up fishing these waters and know the Pass tides in a way that matters enormously when tarpon are stacked in schools below the surface. The season runs from spring through fall; May through July is peak, with fish rolling in visible numbers from the boat.
Gasparilla Adventures — Bike and Golf Cart Rentals
The main rental outfitter in downtown Boca Grande rents bikes, kayaks, SUPs, and golf carts, making it the logistical starting point for almost any active day on the island. The golf cart is the classic island transportation mode — nearly silent, street-legal on the rail trail corridor, and the right tool for exploring without burning time finding parking. Staff know the island well enough to give genuine routing advice, not just a map.
Landmarks & sights
Port Boca Grande Lighthouse and Museum
The 1890 lighthouse at the island's southern tip is one of only six in Florida open to the public and the only one on the Gulf coast. The adjacent museum, housed in the former assistant keeper's dwelling, covers the island's phosphate shipping days, Calusa history, the arrival of tarpon as currency for the wealthy, and old fishing boat relics. Volunteers run it with genuine enthusiasm, and the boardwalk around it offers the best view of Boca Grande Pass.
Whidden's Marina
Sam Whidden founded this waterfront in 1926 as a dance hall and fish house, and the property has stayed in the family ever since, landing on the National Register of Historic Places. The Gasparilla Island Maritime Museum on the grounds holds relics from the early fishing industry, including old fighting chairs that reportedly saw service with notable literary anglers. The atmosphere is quirky and unpolished in a way that the rest of the island no longer is.