According to Florida folklore, Gasparilla Island gets its name from the legendary pirate captain José Gaspar (“Gasparilla“, c. 1756–1821), who had his base on the island and purportedly hid his fabulous treasure there.
Situated above the Boca Grande Pass, just north of Cayo Costa, this island is famous for two things; The town of Boca Grande and the world’s best tarpon fishery. It’s the playground of presidents and Fortune 500 CEOs. You can visit too, as long as you’re willing to pay the 6 dollar toll to cross the old swing bridge from Placida. You’ll pay again to park at one of the public beaches, or you can visit The Southbeach Bar & Grill and skip the parking fee, (if you can find a parking spot).
Having the reputation for hosting society’s elite and for charging to visit, keeps the beaches uncrowded. The wide expanse of white sand leading down to the clear, blue waters of the Gulf of Mexico are a sight to behold.
The Boca Grande Pass is known worldwide for it’s awesome tarpon fishing, and is also the entrance to beautiful Charlotte Harbor.
The old lighthouse on the southern point of Gasparilla has been converted into a museum, and is worth a visit.
Although I could never afford the real estate there, it’s nice to visit once in a while. The anchoring possibilities are either inside Boca Grande Bayou, or just outside behind the golf course. I have taken the dinghy into the bayou from Cayo Costa when the winds are light. It’s a short walk into town from there. Note: there is a public dock available, but dockage is limited to 15 minutes during tarpon season (mid-april thru June). Anchoring inside the bayou means dropping a hook, then backing into the shore and using a stern hook or tying off directly to the mangroves. There is zero swing room. I wouldn’t try it in my boat, but I see boats less than 30 feet do it all the time.