From the DuPonts to the Bushes, the tiny town of Boca Grande on the sprawling island of Gasparilla has thrown out the red carpet for wealthy escapees with a yen for fishing since the early 20th century. That’s when the Gasparilla Inn, Boca’s gracious grande dame, opened and the railroad came to town.
The Inn is still THE place in Boca, especially in January for its annual wine event. It takes up most of the town with its golf course, restaurants, and beach club. But there’s still plenty to explore outside of its campus, including fun shops and restaurants in historic digs such as the old railroad depot and historic theater.
And, of course there’s the beach. Gasparilla Island State Park protects the public access beaches and historic lighthouse, which today holds a small museum. The beach wraps around the island’s south end which borders Boca Grande Pass, a fabled fishing arena for giant tarpon, a.k.a. “the silver king.”
Late spring/early summer is tarpon season, and the town turns rabid with fishermen. In October, however, it practically shuts down.