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.

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 swim in the warm waters of the Gulf of Mexico.

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

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.

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.

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.

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.

Experience the natural beauty and marine life of Southwest Florida up-close with a CLEAR kayak! Don't just take our word on what an awesome tour this is... see our TripAdvisor Travelers' Choice Awards for 2022 and 2023! Paddle Naples' tours are in the top 10% of all worldwide tours! Our Five-Star guided eco-tours and rentals take you through Estero Bay and the Gulf of Mexico’s most incredible paddling routes... including mangrove tunnels, secluded beaches, and prime shelling areas! This is prime habitat for dolphins (year round) and manatees (mostly warm water months). We use top quality standard kayaks and paddleboards that are comfortable and easy to paddle. We have CLEAR paddleboards too, and HOBIE pedal kayaks if needed. Complementary photos included! Looking for something truly unique? Try our CLEAR Kayak Sunset Glow Tour. We will paddle to a secluded beach for shelling until sunset, then we turn on the colorful underwater LED lights and have a great time paddling back!

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.

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 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.

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.

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.

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. You will also learn about the greater Everglades ecosystem and the steps that are being taken to preserve it.

Naples has been rated one of the most beautiful places in the US to paddle. This is because of the beautiful blue waters and the vast array of sea life and wildlife that can be observed in Naples! Guests will have a relaxing time as they paddle through the pristine waters and experience the true beauty of "Natural Florida". While we are on our adventure your tour guide will guide you to all of the areas where we see the most dolphins, manatees, sea turtles, bald eagles, pelicans, osprey, conchs and much more. In fact, there are only a few places in the world to see the West Indian Manatee and Naples is one of them! We were recently featured on the Travel Channel as one of the country's best tour operators and our tours fill up fast so book your tour today for a once in a lifetime adventure.

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

Experience the magical Naples sunset while cruising on our Edison Explorer. This 90-minute sunset cruise takes you from historic Tin City Waterside Shops out to the Gulf of Mexico. Along the way, you will see the southwest Florida wildlife, Keewaydin Island and also enjoy the historical narration provided by expert Captains. Admire some of the most beautiful mansions in Port Royal, an incredibly exclusive neighborhood home to well-known millionaires and move throughout the boat to get the best view, unique photo opportunities and to relax on the water. Choose from one of eleven departure times when you book.

On our 4 Hour Kice Island Shelling Trip we depart from the Goodland Boat Park. Marco Island sits atop the 10,000 Islands. With so many amazing beaches just south of us, only accessible by boat, these islands are littered with amazing shells. Our expert captains and guides will teach you about each individual shell that you find. They will explain their habits, eating behaviors, and how they live in and out of the tides. Our crew doesn’t only know how to identify them, but they know where the best spots are. You will learn identification, and also learn about this unique ecosystem, and why these creatures are so important. Our shelling tour will provide you with the experience of shell combing and you will walk away with new knowledge about sea snails and bivalves.

On your private 2.5 hour guided sunset cruise we often see dolphins, alligators, manatees, sharks, sea turtles and many different species of birds. We observe local marine life in its natural habitat. Getting a personalized experience of a small group is the way to go In the 10,000 islands. With a small group the captain and truly tailor this trip to the guest.

You don’t have to leave Fido behind on this dog-friendly boat tour: bring you furry family member(s) and let them be part of the fun! Stop first at Keewaydin Island for a walk on secluded beaches (and maybe a few frisbee throws). Then, hop back on the boat and enjoy the sunset over the Gulf of Mexico. Non-alcoholic drinks and small snacks are provided. BYO dog treats.

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, SOUVENIR SHELL BAG, BUCKET & SHOVEL FOR KIDS, BEACH GAMES, COMPLIMENTARY WATER, SODA AND SNACK.

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.