6 Group Island-Hopping Tours around Fort Myers & Sanibel

Woman searching for shells on beach

When in Southwest Florida, do as the boaters do and explore our shores. Whether you’re celebrating a special occasion, entertaining meeting attendees, or simply looking for a relaxing way to enjoy incredible weather, your group’s journey begins at the water’s edge. In other words, on the dock of one of these popular tour companies.

Captiva Cruises

As the saying goes around here, variety is the spice of island life. And if there’s one thing this treasured locale has, it’s a huge variety of excursions – from dolphin watching to sunset watching, to shelling at Cayo Costa State Park, to learning about astronomy under a starry sky. Plus, groups with 25 or more people can enjoy up to $5 off each adult ticket, giving you the best excuse to embark on one (or two) of these picturesque Florida cruises.

Ferry at sunset

Estero Bay Express II

Head toward the southern tip of Fort Myers Beach to hop aboard this 40-foot catamaran. Perfect for private group events, a 1.5-hour narrated dolphin tour is accompanied by manatees, osprey and pelicans. There’s also a 1.5-hour sunset cruise that lets you venture into the tranquil backwaters of Estero Bay. Bringing your own food is encouraged, and cameras are pretty much mandatory for the scenery your group will see. Take time to discover Estero Bay Preserve State Park, too.

Fort Myers Princess

With catering capabilities and a full-service bar, this double-decker yacht is no stranger to hosting onboard events. Grab up to 148 other folks and take off for your choice of two 2-hour cruises. The eco tour guides you through Matanzas Pass into the Gulf, passing dolphins, manatees and seabirds along the way. This sunset party cruise comes complete with drink specials and dance music for all ages.

Manatee swimming underwater

Tropic Star of Pine Island

There’s no doubt that this boat’s Cayo Costa shelling cruise is a favorite group travel activity. But if you’re on the hunt for a truly iconic experience, opt for the eco-heritage nature cruise. You’ll journey to secluded Cabbage Key, stopping for lunch at the tiny island’s namesake historic inn. Cabbage Key is a fascinating destination for many reasons. Explore the Cabbage Key Inn, where dollar bills are plastered across the walls and ceiling. Plus, take in Cabbage Key’s incredible history and learn how it was built on a Calusa Indian Mound. 

Shells on the beach

J.C. Cruises

And now for something completely different! Departing from downtown Fort Myers’ eclectic River District, this company’s triple-deck paddle-wheeler can hold more than 300 people – even after accounting for three full-service bars. The novelty vessel offers sightseeing with a side of buffet-style lunch, and cruising west toward the Gulf reveals a few looks into local history (like the Edison & Ford Winter Estates).


Pure Florida

Pure Florida is truly the jack of all trades. Enjoy a wide variety of cruises – from a Matlacha Island cruise where you can learn about the area’s history, nature and wildlife to a wine cruise that allows you to taste fine wines from around the world. With more than 10 different group cruises, you’re bound to find something for everyone with Pure Florida. If you go during the day, you can even get a discounted group price of $25 per person. 


Ready to test the waters? Treat your group to one of the most popular things to do along The Beaches of Fort Myers & Sanibel by planning your tour today!

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