Top Naples Sailing

Come explore Florida's beautiful Paradise Coast aboard a Telstar 28 trimaran sailboat! Watch dolphins put on a show, scour the beach for shells, or simply cruise offshore and feel the wind in your sails.

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.

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.

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.

See the gentle giants of the sea in their natural habitat on this tour. Climb aboard the covered boat and set out along the Florida waterways to spot some wildlife. Alligators, dolphins and all sorts of birds are known to frequent the areas, have your camera ready! The manatees sometimes come right up to the boat for an extra special experience.

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 2.45 hr. Day-Sail or a 2.5 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 (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) Also available is our New 2020 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

Explore the Ten Thousand Islands by boat on a half-day tour to one of Florida’s top natural attractions. Depart from Marco Island, located just south of Naples, with a small group that is limited to 12 participants. Head to an isolated barrier island that is only accessible by boat, where you can snorkel and swim in the warm waters of the Gulf of Mexico.

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.

Even if you’ve never kayaked before, you can still see manatees, dolphins, seabirds, and more in the wild on this Naples kayaking tour. Follow a guide through the protected estuary and mangrove tunnels at Delnor-Wiggins Pass State Park and Barefoot Beach Preserve, learning about plant and animal wildlife from your guide and spotting animals you might miss on your own.

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 Compact Power Boat Tour and travel with a guide and group who won’t let you get lost. You’ll see stunning views of the wildlife refuge, as well as many animals and marine life as you cruise.

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.

Explore the waterways of Delnor Wiggins State Park and Barefoot Beach Preserve by kayak on a self-guided tour near Naples. Get equipped with kayak gear and a waterproof map that highlights landmarks in the preserve. Paddle around mangrove-lined estuaries, back bays, and white-sand beaches, keeping a lookout for dolphins, manatees, and a variety of birdlife. Suitable for all skill levels, no experience needed.