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Gasparilla Island: From Legend to Luxury

Gasparilla Island, Florida is steeped in myths and legends of a nefarious past. Calusa Indians, Pirates, Cuban fishermen, and wealthy captains of industry all had a part in shaping modern Gasparilla Island. The most famous of these was José Gaspar, a Spanish sailor turned pirate who made the area around Gasparilla Island his lair for over 30 years. He plundered ships, and kept women as hostages, or held them for ransom on nearby Captiva Island. Legend has it he was about to retire when he was fooled by the American warship, the USS Enterprise, that was out looking for marauders disguised as a British merchant ship . Though he met his demise, Gaspar's legend survives, and even is the basis for an annual festival held on the island.

It is ironic that the first structure built on the island, the Boca Grande Lighthouse, was used not for plundering, but for assisting ships crossing in and out of Boca Grande Pass, one of the deepest inlets in all of Florida. In 1885 phosphate rock was discovered on the banks of the Peace River just above Punta Gorda, east of Gasparilla Island across Charlotte Harbor. It was this discovery that would turn the south end of Gasparilla Island into a major deep water port and become responsible for the development of the town of Boca Grande. The lighthouse, still a functioning beacon to ships in the area, is also a museum that highlights the history of the island and surrounding areas.

The village of Boca Grande is a step back into "Old World Florida," a carefully preserved part of Florida's history and beauty. The area has seven miles of white sand beaches, no high rise buildings, and no stop lights. Fine restaurants abound. Relaxation is the keyword of the day, and visitors recognize immediately that the pace is friendly and inviting.

The excitement in the area comes from a quest by anglers for another of the area's famous attractions: The Tarpon. Each year, between April and July, the tarpon, or "Silver Kings," run through Boca Grande Pass. These fish, famous for their fight, can reach up to 300 pounds! Boca Grande holds a women's only tournament one weekend, and on the next weekend hosts an event called, "The World's Richest Tarpon Tournament." The winner pockets a cool $150,000!

Boca Grande also offers all the other activities you would expect from an island paradise. Swimming, parasailing, wind surfing, power boating, and golf are available either on the island or right across SR 771 on the mainland.

If you need a break from the beautiful beaches and teeming fishing, Sarasota, with its rich cultural activities, is less than an hour north. Or, take some time and visit historic Fort Myers, located about an hour east.

  1. Elegant, beautifully furnished 3 bedroom luxury villa with pool — Property 72404

    Vacation Villa rental in Gasparilla Island area
    • Villa
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, rural
    • air-conditioning
    Rates (shown in USD)
    $1100 - $1300 per property per week
  2. If Privacy is What You Are Looking for Then You Have Come to the Right Place! — Property 303517

    Vacation House rental in Gasparilla Island area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • air-conditioning
    Rates (shown in USD)
    $1800 - $2150 per property per week

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