Top Maui Sailing Tours

Snorkeling in Molokini Crater is undeniably one of the best parts about visiting Maui. Here in this crescent, submerged volcano off Maui’s southern coastline, over 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet, and swim with schools of tropical fish while cruising the vibrant reef. You can also just sit and suntan on the deck, with sweeping views of Haleakala set just off the back of the boat.

Enjoy stunning coastal views only available from the water during this sailing tour down Hawaii's Au'au Channel. Relax onboard a comfortable, well-equipped sailing yacht with a full captain and crew, enjoying complimentary beverages such as wine, local beer, or soft drinks.

Partake in a time-honored Hawaiian tradition during this private, outrigger canoe sailing experience along Maui's stunning Wailea coast. Learn about Hawaiian culture and history, including the ancient art of canoe construction, sailing, and navigation. Launch the boat from the beach using traditional methods. Spot sea turtles, reef fish, and seasonal humpback whales, with snorkeling equipment provided.

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by handcrafted cocktails and snacks during this sailing cruise from Kaanapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, cocktail and food in hand, as the Hawaiian sky puts on its nightly display. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.

Imagine swimming in a sunken volcano that teems with thousands of fish, while splashing in crystal clear water. On this Molokini snorkeling tour, cruise out to the crater, before jumping in the crystalline waters and scouring the colorful reef. Make a second stop dependent upon conditions, and search for turtles at Turtle Town or a spot named Coral Gardens. This family-friendly Maui activity is one of the island's most popular, and an unforgettable day of exploring the underwater world.

Leave behind the crowds of Ka’anapali Beach and spend the evening on a sunset cruise off the coast of Maui. The perfect romantic evening out, this sunset cruise offers unmatched island views, photo opportunities, and even the chance to spot whales (December–April).

Rather than spending the most magical time of day inside a restaurant or hotel, treat yourself to this sunset dinner cruise aboard a catamaran. Enjoy included drinks and watch the sun go down behind the island of Lanai as you cruise along the Lahaina coastline. Then, indulge in a delicious 3-course dinner accompanied by the sounds of a local musician. Depending on the time of year, you might even spot humpback whales.

Board the beautiful and spacious Pride of Maui catamaran for a sunset cruise near the Molokini crater. Enjoy an open bar including craft beer and blended drinks, plus a generous buffet featuring barbecued ribs, honey-glazed chicken, stir fried vegetables, and more. Watch the sun set, take in a live hula show and if you’re lucky, you may even see humpback whales during mating season.

Set sail into the sunset aboard a sailing yacht with this cruise. You'll hop aboard the Scotch Mist in Lahaina and sail out into the Pacific, where you'll have your choice of champagne, local beers, white wine, soda, juices, and bottled water. Best of all, group sizes are capped at 22 people so you won't have to worry about crowds.

Since 1978, we have been been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to the island as well as its waters; as stewards of our proud culture, we take that responsibility seriously. Our vessel is the widest and most stable on the island, ensuring a comfortable ride for everyone. We provide top of the line equipment, food, drinks, and customer service. Alii Nui’s Sunset Sail is a unique sailing and dining experience. We set the sails and chase the sun as it sinks into the distant horizon on the Pacific Ocean. Toast the day’s end as South Maui’s dramatic shoreline is bathed in a palette of spectacular colors. The Royal Sunset Sail offers a bountiful buffet served inside our spacious cabin. This casual dining experience offers seating in the comfort of the cabin, or enjoy your meal top-side on our spacious deck.

Maui's Olowalu reef and coral gardens which lies off the west coast of Maui, is home to hundreds of aquatic species and is an ideal place to snorkel. Enjoy your cruise to these beautiful snorkeling sites and begin exploring the volcanic gardens. Spend a good amount of time snorkeling and keep your eyes peeled for sea turtles, moray eels, and several fish species.

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience offers seating in the comfort of the cabin or enjoy your meal topside on our spacious deck. A variety of upscale hot and cold appetizers will be accompanied by a wide selection of domestic & craft beers, seltzers, premium red & white wines and champagne, and top tier liquors.

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Nui provides maximum space and comfort. There are plenty of areas to enjoy the "show" from our spacious, shaded cabin or deck areas. A Marine naturalist is always onboard with facts about these gentle giants. A hydrophone will allow you to listen to the amazing songs the humpback whales sing; Maui's best "Whale Karaoke." Our whale watch will run seven days a week from mid-December until the whales go home. Since 1978, Alii Nui Sailing Charters has been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to the island as well as its waters; as stewards of our proud culture, we take that responsibility seriously.

Avoid the over-crowded 30-50 and some with 100-passenger boats. Maui's sunset sail and boat trips are often overpriced and target tourists who don't know any better. We prioritize your comfort and take 15-20 passengers max. You'll enjoy personalized attention and plenty of space to move around. Don't miss capturing the moment when our colorful sails open – it's a sight you won't be able to resist capturing in photos and videos! Winona is not just any sail catamaran; she's Hawaii's only Hawaiian-built, well-kept, and spacious vessel. Get ready to experience true Aloha hospitality, indulge in delicious Hawaiian snacks and drinks, and so much more. Join us for an unforgettable adventure!

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convertible helm and cockpit areas, to the gracious, well-equipped cabin with enclosed head, the 420 is a champion at onboard entertaining and pleasure cruising, whether close to home or way offshore. With so many inviting spaces to settle in for the day, this is the yacht you'll want to enjoy with family and friends. Share Incredible experiences with Hawaii Nautical. Maalaea Harbor is a wonderful starting point for Maui’s best ocean experiences adventures. Join the fun, welcome aboard for world class whale watching, experience top snorkeling spots, and romantic sunset cocktail cruises.

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to the island as well as its waters; as stewards of our proud culture, we take that responsibility seriously. Our vessel is the widest and most stable on the island, ensuring a comfortable ride for everyone. We provide top of the line equipment, food, drinks, and customer service. Snorkeling demo is given to any individuals with all levels of experience. Included in the price of your charters is all snorkeling and flotation equipment, including premium silicon masks, snorkels, and fins, boogie boards, flotation belts, water noodles, wet suit tops, optical masks, and large terry beach towels. Once you have had your fill of snorkeling, enjoy a refreshing "rinse-off" shower with one of four heated fresh-water showers.

Start your day off with an exciting adventure aboard this snorkel tour from Lahaina. Join a small group and set out onto the seas for a sail along Maui's west coast. Your captain chooses a location for the day, depending on weather conditions, for the chance to see green sea turtles and other aquatic species that hang around the coral reefs.

This sunset sail in Maui makes the perfect start or finish to your Hawaiian getaway. Not only does your guide know the perfect spot on the water to see the sunset, but you’ll also enjoy hors d’oeuvres, beer, wine, Champagne, and mai tais as you go. Unlike other cruises, this one sets off on a small boat, making it a more intimate experience for you and other cruise goers.

Sail aboard a catamaran to Molokini crater, one of Maui’s best snorkel sites. The volcanic atoll off the south coast is a natural marine preserve, home to 250 species of tropical fish. Join the crew at the helm of “Paragon II” as Maui’s afternoon trade winds get the boat to this top destination.

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. Our warm, relatively shallow and protected waters make an ideal location for the humpbacks to mate and give birth to their calves. These whales are known for their acrobatics, and are often seen fully breaching out of the ocean!

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. Our warm, relatively shallow and protected waters make an ideal location for the humpbacks to mate and give birth to their calves. These whales are known for their acrobatics, and are often seen fully breaching out of the ocean!