Top Naples Cruises & Sailing

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

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

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.

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.

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.

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.

Our 2-hour cruise is designed for relaxation and deeper discovery. While shorter tours offer a quick look, this experience allows your licensed captain to guide you through the winding canals of Aqualane Shores and Port Royal. Enjoy a front-row view of prestigious waterfront estates—architectural masterpieces hidden from the main bay. With extra time on the water, relax, socialize, and take photos as you cruise calm canals and scenic waterways. Watch for dolphins and native birds along palm-lined shores—without the rough Gulf waters. Step aboard our tropical, hexagon-shaped tiki boat for a fun, personal experience with your captain. Book by the seat (up to 6 passengers) or reserve a private charter. This is a BYOB cruise—bring your favorite drinks and snacks. We provide a cooler with ice, cups, leis, photo props, Bluetooth music, and all required safety equipment. Also consider our Bonita Springs tour launching from The Fish House and our pontoon cruises.

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, couples, and nature enthusiasts. Whether you're a nature lover, photographer, or family looking for a memorable adventure, this tour delivers unforgettable moments in one of Florida’s most scenic coastal regions. Frequent sightings of dolphins, manatees, and native wildlife Visit a remote island for shelling and beachcombing ***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***

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.

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.

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.

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.

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 some of coastal Florida's loveliest scenery, and its wealth of wildlife, on this small-group tour of the Ten Thousand Islands National Wildlife Refuge from Marco Island. Pick from several daily departure times, and set off with just a small group for company. Go on a naturalist-guided boat tour to spot animals like dolphins, pelicans, spoonbills, manatees, sea turtles, and more. Then, disembark at an uninhabited barrier island for a shelling expedition.

Cruise the beautiful waters of Marco Island while taking in the wildlife and making a stop at a remote island for some shelling and beach time. After the beach we check out some of the local hot spots for some catch and release fishing. This trips is a crowd favorite. We customize each trip to the guests to make a unforgettable experience! This excursion lasts for 4 hours. Pricing is for 6 people max. *** Have a Group Larger than 6? We have 2 boats and can take groups up to 12 people. Please reach out to customer service and they will assist you in booking***

Explore Marco Island’s best-kept secrets on this exclusive three-hour adventure, combining wildlife encounters, island exploration, and tubing fun. Unlike larger tours, this small-group experience offers a personalized journey through the 10,000 Islands, where you’ll have close-up encounters with wild dolphins in their natural habitat. Step onto a secluded barrier island—only accessible by boat—and search for rare shells along the untouched shoreline. Then, cool off with a tubing ride in the crystal-clear waters, with your captain adjusting the speed to match your comfort level. Whether you’re looking for relaxation, adventure, or family-friendly fun, this tour delivers it all in one unforgettable trip. Book now and experience the perfect blend of nature, excitement, and discovery on the water!

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.

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!

Join owner and guide Mike on a LED HOBIE GLOW ADVENTURE!!! Our Hobie Pedal Mirage Drives and their powerful LED lighting make our sunset kayak tour unique. Whether you choose to paddle or pedal, your experience will be epic, and allow you to effortlessly go through currents, go further, and see more. The LED glow lights not only highlight the mangrove eco system but make the experience very exciting. Southwest Florida Sunsets are breath taking, as you travel to the beach to watch the sunset, we will search for Dolphins and Manatees, and navigate mangrove tunnels. When we return from the sunset, the LEDs will light your way in an special way.

Hop aboard the best water experience in Naples, where the shimmering Gulf waters become your highway to paradise. We'll whisk you away to the secluded, white-sand shores of Keewaydin Island. Spend your day basking in the sun, shelling along the beach, or exploring the island's lush flora and fauna. We offer two choices on where to be dropped off. The first option, we call it the secret beach, is a much quieter option. It is way less crowded than the main beach on Keewaydin Island, so if you want a more chilled out, quiet, and relaxing experience this one may be for you. The second option is to be dropped off in the heart of the action at the main beach. This is a favorite hangout for locals, buzzing with activity, and there are usually lots of boats (particularly on the weekends). We also provide each passenger a BEACH CHAIR WITH CANOPY, BEACH TOWEL, BEACH UMBRELLA, SOUVENIR SHELL BAG, BUCKET & SHOVEL FOR KIDS, BEACH GAMES, COMPLIMENTARY WATER, SODA AND SNACK.

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.