Top Naples Cruises & Sailing

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.

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

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.

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.

Experience the natural wonders of Southwest Florida on a private 2-hour dolphin and eco tour through the Ten Thousand Islands. Cruise aboard a comfortable boat with a USCG-certified local captain, spotting dolphins, manatees, sea turtles, sharks, and a variety of coastal birds in their natural habitat. Enjoy a stop at a secluded barrier island for shelling and beach time, where you can explore pristine sands and collect unique shells. This small-group tour (up to 6 guests) offers a personalized adventure ideal for families, and couples. Whether you're a nature lover, photographer, or family looking for a memorable adventure, this tour delivers unforgettable moments Frequent sightings of dolphins, manatees, and native wildlife Visit a remote island for shelling and beachcombing Count ALL guest, including children as adults when booking. ***Have a Group Larger than 6? We can take groups up to 12. Reach out to customer service and they will assist you in booking***

Don't just witness a sunset, experience a transformation. Our Naples Sunset Adventure is your ticket to the "golden hour" magic that defines Florida's Gulf Coast. Each evening is a unique, ephemeral performance as the sun kisses the horizon, exploding into a symphony of color that paints both the sky and the shimmering water. This is where cherished memories are forged, where the kids gasp in wonder, and where couples find a moment of perfect romance. Let us guide you to the heart of this nightly wonder, creating an unforgettable highlight of your Naples vacation.

Explore the thousands of islands around Marco Island by Go Cat boat. Whether you're an experienced boater or a complete novice, these two-person fiberglass boats are fun and easy to drive and maneuver, which means that exploring the mangroves, while looking for dolphins, manatees, and many different birds, is a breeze.

Enjoy hours of tranquil island shelling on this small-group boat trip from Marco Island, Florida. Soak up the scenery and keep a lookout for local marine wildlife on the boat trip over to and from your beach destination that’s only accessible by boat. Learn more about the different types of shells you find and the local ecosystem from your captain and crew.

Explore the waters around Marco Island on a private boat excursion combining wildlife viewing, shelling, beach time, and catch-and-release fishing. Cruise to a remote island for time on the beach before heading to local fishing spots, with the flexibility to tailor the experience to your group's interests. Limited to six guests, this is a versatile way to spend a day on the water without having to choose between different activities.

Kick back, relax, and let your captain set sail for the sunset with you and your party on this private cruise from Marco Island, Florida. Feel free to bring a cooler packed with your favorite food and refreshments, alcoholic and otherwise. Stop off at a secluded beach for some shelling, and keep your eyes peeled for local wildlife such as dolphins, alligators, manatees, and coastal birds.

Southwest Florida is home to a diverse ecosystem and marine life. See where the Gulf of Mexico and the waters of the Everglades converge during this sunset cruise. You’ll begin your sail in Naples then head out into the Everglades in search of alligators, sharks, and manatees. Then, you’ll ride through the Everglades National Park to the 10,000 Islands where more wildlife awaits. Finally, you’ll gaze at the sunset before heading back to Naples.

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.

Explore Ten Thousand Islands, Keewaydin Island and more aboard our luxury pontoon. Private 2 ½ hour luxury pontoon tour Accommodates up to 6 guests Eco/Nature Tours Island hopping Shelling

Ahoy Matey! If you are captivated by stories of infamous pirates and legendary mobsters, then this is the tour for you! The Ten thousand Islands are abundant with tales of notorious pirates, nefarious mobsters and legendary ghost ships. On this distinctive tour, you will be regaled with stories of the area, including the legendary lost treasure of the Ten Thousand Islands, ghost ships witnessed by multiple people, the infamous pirate that's known worldwide who used to hide out in the area, and mobster influences in the Everglades. In addition, as you float toward the Everglades you’ll learn why the Canal here was made, and what the notorious local historic hotel was originally designed for. You’ll be taken to an abandoned beach that pirates and swashbuckling buccaneers have lived in days past. This tour is full of rich history, exciting tales and captivating stories, allowing you to walk on the same sand that pirates once roamed. Climb aboard and book your adventure today!

Begin your day with a peaceful private cruise through Naples Bay, where the calm morning waters create one of the most beautiful times to experience Naples by boat. Your 2 hour journey takes you through the scenic waterways of Naples and Port Royal, one of the city's most prestigious waterfront neighborhoods, known for its remarkable estates and coastal setting. As you cruise, enjoy a complimentary breakfast accompanied by coffee and orange juice while your captain searches the surrounding waters for dolphins and other local wildlife. Keep your camera ready: dolphins are frequently seen in the area, along with manatees, ospreys, pelicans, and other native marine and bird life. Because these animals are wild, sightings cannot be guaranteed, making every encounter a special part of the experience. With the boat reserved exclusively for your group, there is no need to rush. Sit back, enjoy breakfast, take in the morning breeze, and experience a quieter side of Naples from the water.

Paddle the waters of the Naples coastline on a paddleboard or kayak while you try your luck at spotting some local wildlife with the help of a guide. Not only are you in with a chance of seeing manatees and dolphins, but sea turtles, bald eagles, and pelicans too. Take in the area’s beautiful scenery from the water and dive into the adventure.

The exclusive Go Cat Boat is a luxury catamaran. This is the newest and coolest way to explore the 10,000 islands around beautiful Naples Bay! Check us out on the web gocatsonthewater dot com. We visit unique mangrove tunnels and winding waterways. Super comfortable and super easy to drive; great for first time boaters or experienced mariners. It is real fiberglass boat (unlike those plastic boats) and sooooo fun to drive. We have local guides who know history, sea life, birds, manatee, dolphin, eco systems and local lore. Guaranteed to put smiles on everyone's face or your money back. Free pictures capturing the beauty and sea life. Don't hesitate to take this tour, check out our reviews, you'll love it!

Nature lovers can spend a day immersed in pristine landscapes on this shelling cruise from Naples, Florida to Keewaydin Island. Join a small group and board your vessel for the journey to the remote island. Cruise past mangrove forests and see wildlife such as alligators, dolphins, and even manatees along the way. Once you reach Keewaydin, take a nature walk and fill your big with beach treasures before heading back.

Relax on the water and enjoy stunning views of Naples Bay on a sunset cruise. The boat seats six guests, letting you skip the crowds and enjoy a more personalized experience. You may also see local wildlife such as dolphins, manatees, ospreys, and more. You don't need to worry about bringing anything, since snacks and drinks come with the cruise.

Enjoy a private sunset tour for up to five people. During the trip, look for wild animals such as dolphins, blue herons, egrets, and roseate spoonbills. Stop for a swim at Keewaydin Island, take a walk on a secluded beach, or collect a few souvenir seashells. Learn about the greater Everglades ecosystem and the steps being taken to preserve it on this private boat tour.

- Visit beautiful Keewaydin Island, accessible only by boat - Choose between our peaceful Secret Beach or lively main Keewaydin beach - Enjoy a scenic cruise through Naples Bay and mangrove waterways - Look for wild dolphins, manatees and coastal wildlife - Beach chairs with canopies provided for every guest - Beach towels, umbrella, cooler and beach games included - Souvenir shell bags provided for shelling - Bucket and shovel available for children - Complimentary bottled water, soda and snack - Small-group experience with a maximum of 6 guests - Complimentary marina parking just steps from the boat Secret Beach: Our quieter option for guests who want to relax, shell, swim and enjoy a less crowded part of the island. Main Keewaydin Beach: The livelier side of Keewaydin and a favorite gathering place for local boaters, particularly on weekends. We recommend bringing sunscreen and bug spray, along with anything personal you would like for your time on the island.

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.

Florida's south-west coast is filled with sea life, wildlife, and nature sightseeing you won't want to miss. This Naples Bay and Gulf of Mexico Private Eco Tour by Boat takes you to areas along the water in Naples Bay and the Gulf of Mexico so you can see a variety of animals and fish in their natural habitat. Plus, a guide narrates so you can learn about the ecosystem, too.