Top Naples Cruises & Sailing

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.

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 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

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 to watch a breathtaking sunset while sipping your favorite cocktail. 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. Guests are welcome to bring small coolers with their favorite beverages and snacks. Alcohol is permitted. Please note this is not a private boat tour, this is a group tour with others onboard Boarding time is 15 minutes prior to scheduled departure time. Please allow enough time to park and walk down the dock. We leave promptly on time.

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.

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.

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***

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.

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.

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.

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!

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.

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.

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 serene sunset cruise in Naples Bay aboard a comfortable New Godfrey boat, accommodating up to 6 guests for an intimate experience. As you glide over the tranquil waters, keep an eye out for dolphins, manatees, and ospreys while soaking in the breathtaking views of the sunset. Your knowledgeable captain will share insights about the local marine life, enhancing your understanding of this beautiful ecosystem. Perfect for couples, families, and friends, this cruise includes everything you need for a relaxing evening—water, wine, soda, charcuterie and blankets for added comfort. Private boat cruise for up to 6 guests, ensuring a personalized experience Observe local wildlife such as dolphins and manatees in their natural habitat Learn about Naples Bay’s marine life from your friendly captain Complimentary snacks, drinks, and blankets included for your convenience

Feel the gentle breeze as you cruise through the canals of Naples Bay; Enjoy a complimentary breakfast as you take in the beauty of the morning; Spot playful dolphins, manatees, and seabirds in their natural habitat; Relax on a luxury pontoon and soak in the elegance of a coastal paradise

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.

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. * Please note this is a catch and release trip* *** 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***

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.

This is the only tour of its kind around Marco Island! Experience the best of the 10,000 Islands on this exciting dolphin-watching and tubing adventure. Cruise through mangrove-lined waterways, spotting wild dolphins playing in their natural habitat. Then, switch gears for some fun as you float and glide across the water on a tubing ride, perfect for all ages. This private, small-group tour offers a unique mix of wildlife viewing and thrilling water activities, making it an unforgettable way to explore Southwest Florida’s scenic coast. Book now to combine adventure and relaxation on the water!

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.