Captiva Island Charter Touring

Local charter tours You can sail for a full day, go to Cabbage Key for lunch or enjoy a picnic lunch on the beach on Cayo Costa.

According to the local folklore, Captiva Island was the place the legendary pirate captain Gasparilla held his female captives for ransom or worse. The island was once the home of the Calusa (Fierce People), a tribe of 50 thousand warlike people who did not welcome explorers, but who were decimated in the 1700s nevertheless. It was the site of a spectacular shipwreck in the 1880s which left the lone survivor, the Austrian, Binder to live as a real life Robinson Carusoefor ten years. His grave can still be found in the tiny cemetery by the Chapel of the Sea. Theodore Roosevelt used to fish on the east side of the Island in the channel that bears his name. Pepperidge Farm created a dark brown brownie cookie named after it. This is a place rich in mystery and romance. You will want to book a local charter tour.

There are a number of charter fishing and nautical excursion companies around the island.

Captiva Cruises, a leader in the Florida ecotourism industry, offers excursion boat tours which honor the island’s history and environment. The Dolphin Watch and Wildlife Cruise takes you and your party along Pine Island Sound for an introduction to the natural environment of the island. The Out-Island Cruise is a half-day excursion around neighboring islands, Cabbage Key, Useppa Island, Boca Grande, and Cayo Costa. Private sailing cruises aboard the Adventure or charter group cruises aboard other spacious vessels can be arranged as well.

Captiva Kayak Company offers guided Kayak trips in the waters around Captiva. See manatees, osprey, cormorants, mangroves and mangrove tree crabs. The informative guides share the history of the island as well as the wildlife and hints about where to dine.

New Moon Sailing will take you sailing along the protected waters of Pine Island Sound or out into the Gulf of Mexico. You can cruise along the beaches and watch the bathers and race the dolphins as they jump in the wake of the boat. You can circumnavigate the historic island in half-day trips. You can sail for a full day, go to Cabbage Key for lunch or enjoy a picnic lunch on the beach on Cayo Costa. You can swim beside the manatees. You can sail up to Boca Grande for a full day tour. Trips longer than one day can also be arranged.

Sea Oats Captiva Island Luxury Estate is the largest and most luxuriously appointed home-away-from-home on the island, perfect for corporate retreats or family holidays. Please contact us for our concierge and planning services.