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A small sailboat in the middle of a large body of water

Boating Adventures in Fort Myers

From island-hopping for lunch to sunset dinner cruises, being out on the water is one of our favorite ways to spend a day in the Fort Myers area. With so many bodies of water to choose from, your choices are practically unlimited: Charter a boat in the Gulf of Mexico, go on an eco-tour to see dolphins and other wildlife, join an expert guide on a private fishing excursion and get into the vacation spirit on a pirate ship or tiki boat.

The appeal of Fort Myers boating is not just the sun shining on your shoulders and miles of sparkling water around you. It also comes from passionate captains who love every moment of their job and know these waterways like the back of their hand. For example, Captain Brian Holaway is a certified Florida Master Naturalist who deftly navigates Pine Island Sound to bring you out for a day of shell-collecting and stopping at the world-famous Cabbage Key Restaurant for lunch. On a catamaran with Captain Cathy Madigan Eagle — known by locals as “the dolphin whisperer” — you’ll enjoy more than a boat ride; it’s a day filled with delight as you cruise around barrier islands and beyond to see bottlenose dolphins, manatees and even jumping mullet.

Fishing is a year-round sport in Fort Myers and its nearby islands, beaches, and neighborhoods; long considered an angler’s paradise for both inshore and offshore fishing. Tarpon fishing is world class, but even if you’re not ready to seek out the mighty silver king, you’ll find abundant saltwater fish like snapper and redfish, plentiful snook in the back bays, and trout and largemouth bass in the freshwater canals and Caloosahatchee River. Charter a guided boat tour and ask about local restaurants that can cook your catch just the way you like it.

A dolphin swimming in the ocean with its mouth open

It’s always a swashbuckling good time in Fort My-arrrghs onboard a Spanish galleon. Salty Sam’s Pirate Cruise offers all-age outings and adults-only cruises that bring a treasure trove of fun on board with interactive comedy, games and dancing. Or choose to charter a floating tiki bar where you and your friends (old and brand new!) can sail through the beautiful waterways with cocktails in hand.

If vacation is just about the only time you can truly appreciate a sunset, why not enjoy it on the water? Take a comfortable ride on a catamaran from one of the many sunset cruises available in the area and enjoy a relaxing and peaceful time as the sun sinks down over the Gulf of Mexico. Or reserve a spot on the 100-foot Sanibel Harbour Princess Yacht that sets sail at the golden hour, accompanied with dinner on board.

Couple Shore Walk

Join the locals on their favorite pastime by cruising the waters in Southwest Florida, and find more on-the-water activities throughout your stay.