Top Maui Sailing Tours

Relax in the Maui sunset, taking in orange and pink evening skies as you glide over the waves on this catamaran trip including dinner. Take in seascape views from the boat’s spacious deck which features unobstructed views of the ocean, or sip a tropical drink at the fully licensed onboard bar before tucking into a dinner crafted from fresh local ingredients. A professional photographer onboard captures magical memories available for purchase.

Spend the morning on the water off the Maui coast aboard a 64-foot catamaran sailing to Lanai’i. The expert crew will find the best reefs to snorkel so you can see incredible underwater sea life. After your snorkel, return to the boat for lunch and stunning sea views in the golden afternoon light. Look out for playful spinner dolphins on the sail back to Maui.

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buffet lunch is served and our complimentary bar is open after you are done snorkeling. We hoist the sails and return to Ka'anapali Beach while viewing the amazing coastline of Maui. Note: We are a beach loading catamaran and you might get wet up to your knees boarding.

Sail along the Maui coast on a 47-foot catamaran at sunset for an unforgettable evening adventure—and leave the logistics to someone else. Set off from Lahaina and enjoy the majestic Maui ocean scenery during the colorful sunset hours. A selection of hors d'oeuvres, wine, beer, and non-alcoholic drinks are available on board so you can relax and have fun.

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.

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kaho‘olawe. Guests can relax on trampolines or in shaded seating while enjoying locally-inspired appetizers and a selection of beverages, including cocktails, beer, and wine. From December to March, keep an eye out for majestic humpback whales as they migrate, often providing unforgettable sightings during the sail. - Enjoy a scenic 2-hour sunset sail aboard the 55-foot Akialoa catamaran. - Indulge in a selection of local appetizers and an open bar of drinks. - Limited to 48 passengers, ensuring a cozy and intimate experience. - Spot migrating humpback whales from December to March for a unique wildlife encounter.

Embark on a once-in-a-lifetime family adventure, where sun, sea, and stunning sunsets come together for the perfect day on the water! Whether you’re snorkeling or simply soaking in the views, there’s something for everyone to enjoy. This unforgettable journey perfectly blends adventure, family fun, and the awe-inspiring beauty of a Maui sunset-creating lasting memories to cherish forever. Join us for an extraordinary afternoon and evening on the water!

Embark on an unforgettable sunset sail in Maui where everything is taken care of to ensure a fun and relaxing time. As the sun sinks into the gentle waves, enjoy craft cocktails, wine, and beer at the open bar. Experience a golden happy hour at sea with music and drinks to get your Maui night started in style.

Cruise Maui's scenic coastline on a sunset outing aboard a catamaran whose two hulls offer increased stability, more deck space, and a sheltered cabin equipped with restrooms—all designed for a comfortable ride. An evening departure time makes the most of sweeping views along the shore, as the sun sinks over nearby Lanai. Stay refreshed with included soda, juice, and water, or visit the galley to purchase alcohol and snacks.

Join us for an unforgettable West Maui Snorkel & Sail adventure! Departing from Maalaea Harbor, we’ll explore the coastline, stopping at the day’s best snorkeling spots to discover vibrant coral reefs, sea turtles, and diverse marine life. After a thrilling underwater experience, enjoy a delicious deli-style lunch and drinks. With stunning views and a relaxing sail, this excursion offers the perfect mix of adventure, nature, and relaxation.

Experience an unforgettable catamaran cruise in Maui with two snorkeling stops—and leave the logistics to someone else. Sail from Kaanapali Beach to snorkel at two reefs, with the chance to swim with sea turtles and other marine wildlife. While on board the boat, you’ll enjoy breakfast, a BBQ lunch, and an open bar. Don’t forget to look out for dolphins and whales (in season)!

Experience an unforgettable catamaran cruise in Maui. Sail on a 65-foot boat along the Pacific Ocean where the professional crew takes care of everything—including photos (fee to purchase). Snorkel at a reef with guaranteed sea turtles, and after enjoy a taco lunch on the boat with margaritas and beer. Relax on the cruise back to Maui—look out for whales in season and beautiful views all year long.

Discover the clear blue waters of Molokini Crater with a guide to make sure everyone is having fun and staying safe on this group snorkeling experience. Begin with breakfast on board, and end with lunch before you head back to the harbor. In between, go snorkeling and look for sea turtles in the summer and whales in the winter.

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.

Leave the crowds of Ka’anapali Beach behind and step onto a premium sunset dinner cruise, where Maui’s coastline sets the stage for an unforgettable evening. Perfect for capturing stunning views, snapping share-worthy photos, or even spotting whales (if you’re visiting between December and April), this experience adds just the right amount of romance to your getaway.

Sail along the Maui coast on a humpback whale-watching excursion in the ʻAuʻau Channel—and leave the logistics to someone else. See these gentle giants spouting, tail-slapping, and maybe even breaching in their natural habitat from a comfortable boat, crewed by local experts. Enjoy the comfortable boat, ocean scenery and wildlife spotting, and look out for mother and whales and their calves because this is their winter breeding ground.

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.

Choose your own adventure after you set sail from Maui to Coral Gardens on this cruise. You get three activities in one excursion: sailing, snorkeling, and whale watching. Spend your time in the water, relaxing on deck, or enjoying the buffet-style lunch and drinks. As a bonus, the tour also includes reef-safe sunscreen to protect you and the environment.

Board the beautiful and spacious "Pride of Maui" catamaran for a relaxing sunset dinner cruise. Enjoy an open bar featuring craft beer and blended drinks, plus a generous buffet complete with barbecued ribs, chicken, roasted 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.

This afternoon sail in Maui offers a chance to see humpback whales in the ‘Au ‘au channel. Enjoy snacks, water, sodas, and alcoholic beverages aboard a small boat for an intimate experience focused on whale watching. Chat with your crew along the way and learn all about whale behavior as you keep an eye out for the majestic marine mammals.

The waters off the coast of Maui are often home to majestic humpback whales. Set sail from West Maui on this catamaran whale-watching tour as you attempt to catch a glimpse of the marine giants in their natural habitat. The onboard hydrophone will even let you listen to the whales’ song as you travel.

Snorkeling in Molokini Crater is a frequent bucket-list experience for Hawaii visitors. Here in this submerged volcano off Maui’s southern coastline, more than 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet (23 meters), and swim with schools of tropical fish. This half-day tour from Maalaea Harbor takes care of all the logistics for you.

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by cocktails and snacks during this sailing cruise from Ka’anapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, drink and food in hand, as the Hawaiian sky puts on its nightly display. Plus, keep your eyes peeled for local marine life, including whales from mid-December to mid-April. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.