Boating & Sailing Charters

Welcome aboard the Pieces of Eight, a magnificent 65ft replica Spanish galleon pirate ship pillaging and plundering the Gulf of Mexico from the shores of Fort Myers Beach. Pieces of Eight, an authentic pirate themed cruise is looking for buccaneers young and old to experience a real-life pirate voyage back through the Golden Age of Piracy. You are guaranteed to have a jolly roger of a good time.

Backwater Fishing Trips, Sealife Encounters, Morning, Afternoon & Sunset Dolphin Cruises, Shelling & Lunch Excursions, Island Trolley Tours, Wedding Cruises, and more!

Complimentary Trolley to & from your hotel/condo in Sanibel.

We also offer private charters and activities whether your group is large or small; Island Trolley Tours, Wedding Cruises, and more! We are sure that we can tailor fun

Unobtrusive dolphin encounters, shelling, wildlife sightseeing, and historical narrative led by Captain Steve Plein of Captiva Island's very own New Wave Eco Charters. Chosen as one of In Flight Network's ''42 Best Eco Adventures of 2017 in the United States.'' Experience the barrier islands and their surrounding inhabitants in an up close and personal manner

Sanibel resident Captain Brandt Symes is a full time, professional guide offering private inshore FISHING CHARTERS, SHELLING TRIPS, LUNCH CRUISES, SIGHTSEEING and ECO-TOURS. From novice to die-hard angler, we fish the shallow waters of Sanibel, Captiva and Pine Island Sound for Redfish, Snook, Tarpon, Sea-Trout, Shark, etc. We genuinely enjoy taking families fishing! LGBT friendly. Up to 6 people.

America’s #1 Sailing School has taught over 140,000 adults and families how to sail at all levels. From two days to weeklong sailing courses with resort accommodations, you will learn how to skipper a boat up to 50’. Offshore Sailing School’s fleet includes Colgate 26 sailboats, and 40’-50’ cruising yachts and catamarans on Captiva Island, Ft. Myers Beach, and Cape Coral, Florida.

SANIBEL AND CAPTIVA ISLAND'S MOST EXCITING BOAT TOUR

You will cruise the waters of the Gulf of Mexico and Pine Island Sound, circumnavigating the shores of both Sanibel and Captiva Islands. During the narrated tour and dolphin watch you will be amazed to see that even the dolphins are thrilled with the Sanibel Thriller.

The Sanibel Thriller also offers the boat as a private charter....