Top Naples Sailing Tours

Set sail from Naples aboard a spacious catamaran that cruises along the Gordon River, Naples Bay, and drops anchor at Keewaydin Island. This half-day cruise takes you to pristine white-sand beaches where you can go swimming and shelling. Hear live commentary about the sights along the way and keep an eye out for dolphins. The catamaran accommodates up to 44 passengers and is suitable for all ages.

Immerse yourself in some of Florida’s loveliest scenery—and enjoy a relaxing excursion out on the water—with this private sailing tour. Meet your guide in the afternoon in Goodland, hop aboard your stiletto catamaran, and set sail. You’ll tour the Ten Thousand Islands region, known for its lush seascapes, mangrove forests, and wealth of wildlife. Your guide will point out landmarks and highlights as you go.

Discover the sights and marine life of Naples on a sightseeing cruise. You have the opportunity to see birds, dolphins, and, season permitting, manatees. The cruise also takes you past the area’s top mansions, Keewaydin Island, and more. Relax and learn about local history, wildlife, and celebrity real estate during on board commentary. It’s the perfect time to take unobstructed photographs of the city and its natural surroundings.

Set sail into the glorious Gulf of Mexico for a luxurious 2.5-hour Catamaran day sail, aboard the beautiful 42ft. MaineCat Cool Beans. Journey to an exclusive island paradise where you can bask in the sun and take part in some exciting shelling (weather permitting). Relax with pristine views as calming island tunes fill your ears, while sipping on complimentary drinks from comfortable seating—with the choice of basking indoors or outdoors. Create memories with your loved ones on the high seas.

Set sail on this beautifully appointed Catamaran, "Cool Beans", and start making lasting memories! Cool Beans Cruises is the perfect way to see SW Florida, By Water! Choose from a 2.5 hr. Day-Sail or a 2 hr. Champagne Sunset Cruise. With quick access to the Gulf of Mexico, you will experience true sailing with limited motoring. A stop for a swim to a secluded pristine beach for shelling can be part of the Day Sail Only(weather permitting). Keep your cameras ready to capture a photo of the local wildlife to see along the way! Cool Beans Catamaran will accommodate up to 20 passengers. PRICE INCLUDES SODA, WATER, BEER, & WHITE WINE . A CHAMPAGNE TOAST AT SUNSET IS INCLUDED FOR THE SUNSET CRUISE. Please note that parties of 7 or more, an 18% gratuity is added to our base price and is due and payable to the Captain. Also available is our 25 Ft .Pontoon, Lil' Beans! Perfect for up close eco/nature /shelling and island hopping. Book a Private tour for a group for up to 6 guests

See the gentle giants of the sea in their natural habitat on this Everglades wildlife tour. Climb aboard the covered boat and set out along the Florida waterways to spot manatees, alligators, sharks, birds, and more. Learn about the local ecosystem and wildlife from your Coast Guard-certified captain and keep your eyes peeled for manatees that sometimes come right up to the boat.

Cruise aboard the Double Sunshine from Naples and into the Gulf of Mexico at sunset. Move freely on the deck to see the best views and capture lovely pictures. You may be able to spot dolphins or manatees swimming in the gulf. Cruise past stunning mansions in exclusive Port Royal, serene Keewaydin Island, and enjoy the tales of Florida history from your knowledgeable captain.

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico. Cruises are narrated to point out interesting sights along the way. Dolphin sightings are plentiful and fun for all ages. Pack your favorite drinks and snacks in a cooler, and don't forget to take some pictures! We've been cruising the Naples Waterways since 1991 and are family-owned and operated.

Explore the Ten Thousand Islands by boat on a small-group cruise tour to one of Florida’s top natural attractions. Depart from Marco Island, located just south of Naples. Head to an isolated barrier island that is only accessible by boat, where you can swim in the warm waters, search for shells, and look for marine and other wildlife.

Get an up-close view of Florida’s spectacular, coastal mangrove forests—and enjoy an active way to explore—on this kayaking or paddleboarding tour. Pick from multiple tour times, head to the departure point, and meet your guide: after an introduction to your kayak or paddleboard, you’ll hit the water. Paddle through mangrove tunnels, have the chance to spot wildlife like dolphins and manatees, and learn more about the forests from your guide.

Look for dolphins in the waters of the Ten Thousand Islands on this boat tour from Marco Island. With a captain-guide, explore a piece of Florida's gulf coast to see and learn about the natural environment. You also have the opportunity to spot shorebirds with your live guide on hand to identify them.

Exploring the Ten Thousand Islands National Wildlife Refuge on your own can be intimidating if you don’t know your way around on the water. Book this Thousand Islands 2-person Catamaran Tour to follow a knowledgeable guide who will keep you from getting lost and ensure you enjoy this pristine preserve to the fullest, with great opportunity to view the wildlife and sea life that inhabit the refuge.