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Just northwest of Bokeelia, across the choppy tarpon-packed waters of Boca Grande Pass, sits Gasparilla Island and the town of Boca Grande. If Sanibel is the spot for a certain type of affluent nature lover, and if Pine Island attracts quirky off- the-gridders, then this particular barrier island is the scene for the sort of person who summers in Martha’s Vineyard. Preppy and upper crust but with a certain relaxed charm, Boca Grande makes for a genteel day trip.


Where to Stay

The Gasparilla Inn (500 Palm Ave., Boca Grande; (800) 996-1913; is indisputably the place to lodge on the island. Originally constructed in 1911 as a refuge for wealthy northeasterners seeking to escape the bitter winters, its reservation books have long been filled with names pulled from the social register.


The old pier.

Where to Eat

For crab cakes and grouper sandwiches, swing by the Loose Caboose (433 Fourth St. W., Boca Grande; (941) 964-0440;, an island-casual eatery set inside the historic train depot. The Temptation (350 Park Ave., Boca Grande; (941) 964-2610), affectionately known by locals as The Temp, offers white-tablecloth dining and a menu where Gulf seafood shines. And The Pink Elephant (491 Bayou Ave., Boca Grande; (941) 964-4540), set inside the historic and elegant Gasparilla Inn, offers a relaxed alternative to the inn’s more formal dining room.


Where to Shop

If Boca Grande had a uniform for women, Lilly Pulitzer would be its supplier. Swing by The Palm on Park (444 4th St. E., Boca Grande; (941) 964- 4448) for tropical prints in bright pastels. For a wide selection of island souvenirs in a historic setting, try Fugate’s (428 Fourth St. W., Boca Grande; (941) 964-2323). Opened in 1916, the department store has been serving tourists and locals for more than 100 years.


Where to Visit

The Boca Grande Lighthouse Museum (880 Belcher Road, Boca Grande; (941) 964-0060; sits at the southern tip of the island and offers a glimpse around its old- est structure. Built in 1890, the building served as both a lighthouse and home for its keepers. Today, it offers a five-room museum filled with artifacts from Florida history. The beach in front of the museum, part of Gasparilla Island State Park, has powder sand and views of nearby Cayo Costa, though the water here is off-limits to swimmers because of the strong currents.


Where to Fish

Boca Grande Pass is world-famous for its tarpon, and there are plenty of guides available to reveal the best spots to drop a line. Local favorite Capt. Chris Slattery of Reel Intense Inshore Charters (941) 468-1618; is known as the “tarpon whisperer” and has a reputation for drawing in fish when other boats can’t get a bite.


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