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.

Avoid the over-crowded 40-50 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 30-40 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!

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.

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-up perspective when viewing Maui's natural inhabitants above water and below. With spacious seating, Koa Kai allows for optimum viewing for all participants. A snorkeling demo will be given to any individuals will all levels of experience.

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.

Catch a wave of excitement as you learn to surf during this 2-hour beginner’s, small-group, lesson in Maui. Join no more than 6 other students for an introduction to the fundamentals of surfing, including ocean awareness, water safety, riding skills and proper etiquette. You’re guaranteed to be surfing in one easy lesson, or your next lesson is free! An instructor, surfboard and rash guard are all included.

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.

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.

Unwind after a day of exploring Maui on a sunset cruise with a 4-course dinner. Enjoy delicious cuisine and included Mai Tais and other beverages against the stunning backdrop of the Pacific Ocean and surrounding islands of Lana'i and Moloka'i. With a limited number of guests aboard, this makes for the ideal romantic experience.

This Maalaea Harbor Sunset Dinner Cruise from Wailuku is perfect for couples or anyone looking to add a beautiful, sunset experience to their trip while in Maui. When booking, choose from multiple dinner options such as prime rib, baby back ribs, and a vegetarian penne pasta. During your cruise, sit back with tableside service and drinks included as your captain and crew take care of the rest and you take in the sunset with island-style music playing in the background.

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.

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.

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.

Sail along the coast of Maui and enjoy a stunning Hawaiian sunset during this evening cruise from Lahaina Harbor. Get comfortable on a spacious catamaran and enjoy the views while you enjoy complimentary hors d’oeuvres and non-alcoholic drinks. If you’re traveling between December and May, you may even spot humpback whales while you sail.

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.

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.

Join us on this thrilling snorkeling adventure at one of Maui's premier Pali Coast. Then enjoy a leisurely sunset cruise to experience a relaxing Maui sunset. (Trip location can be subject to change due to weather and ocean conditions, as the Captain sees fit for safety and well being of the guests.) A snorkeling demo is given to any individuals with all levels of experience. Included in the price of your charter is all snorkeling and flotation equippment, including premium silicon masks, snorkels, and fins, flotation vests, and optical masks. This tour operates April 16 - December 14. Check out our Koa Kai Sunset Whale Watch from December 15 - April 15.

Leave the chaos of the mainland behind when you embark on this sunset cruise in Maui. An exclusive experience for up to six guests, this trip takes you through multiple natural landscapes, from the Molokini Crater to the Kahalewai Mountains and Lanai Island. Take in views of the coastlines and island volcanoes and relax as you watch the sun setting with your chosen group. You even have the chance to catch a glimpse of the green flash phenomenon.

Join us on a thrilling snorkeling adventure at Molokini Crater, then experience close encounters with Maui's most famous visitors, the humpback whale in Ma'alaea Bay! A snorkeling demo is given to any individuals with all levels of experience. Included in the price of your charter is all snorkeling and flotation equippment, including premium silicon masks, snorkels, and fins, flotation vests, and optical masks. This activity operates from December 15 - April 15. Check out Koa Kai's Molokini Snorkel tour from April 16 - December 14.

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.

The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Gardens which boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Enjoy the best conditions of the day, on the water as the world wakes.

LIVE DJs on board, amazing dance music, and sound systems. Day trip or sunset on the water with warm weather and breathtaking views - meet and party with locals and other visitors. Bring your own drinks on board for more fun.

The Au’au’ Channel is best known for its concentration of humpback whales. Hop on a boat in Maalaea Harbor to sip on a drink and spend time in the whales’ natural habitat. Your guide not only offers a trained whale-spotting eye but ensures you learn about the animals’ behavior and migration patterns. Don’t forget your camera: Lucky visitors get the chance to see the whales breaching in the open water.