Boating & Sailing Charters

Island Time Cruises offers a variety of activities you can experience out on the water. All trips are private and can be customized to meet your needs.
Shelling Excursions
Dolphin Tours
Eco & Historical Tours
Out Island Lunch Trips

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.

Fabulous out island excursions to Cabbage Key, Useppa and Boca Grande for lunch or Cayo Costa State Park for shelling as well as Dolphin Adventures, Sunset Serenades, Sailing Cruises aboard our 24 passenger sailing catamaran, naturalist led shoreline discovery and starlight tours, private charters and custom expeditions. An excursion with Captiva Cruises is sure to be the highlight of your trip!

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.

Ready for a Sailcation? Learn how to ''sail away'' with Offshore Sailing School and go from the couch to the Captain's chair in just 3 days.

2 locations: South Seas Island Resort on Captiva Island & Pink Shell Beach Resort & Marina on Ft Myers Beach.