Top Maui Sailing Tours

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.

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that made Teralani famous.

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.

Embark 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, as well as a selection of snacks. 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.

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.

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite sphere of color, surrounded by the islands of Maui, Lāna‘i, and Moloka‘i. Enjoy the best of performance sailing in Maui on our Conser 47' performance sailing catamaran. With spacious trampolines, shaded cabin seating, and a professional crew, this is the ultimate Maui sunset cruise. We invite you to relax, sip a cocktail, and watch the sky transform over the Pacific. Your sunset sail includes local appetizers and a full open bar with sparkling wine, white wine, and local beer. Experience the magic of Maui. This tour is perfect for all ages, with a limited capacity of 25 passengers ensuring a cozy atmosphere.

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.

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.

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.

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.

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and delicious island-style pupus as you glide over the calm waters, led by a captain who knows the best spots. Experience the beauty of Maui, whether at the crater’s edge or hidden coastal treasures, while soaking in the sun and the vibrant atmosphere on this relaxing cruise. - Relax on the widest sailing catamaran in Maui - Discover the best water spots, from Molokini to turtle sanctuaries - Enjoy hand-shaken Mai Tais and island-style pupus onboard - Ideal for those looking to unwind and experience Maui's beauty

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.

Dive beneath the waves to explore Maui’s colorful fish, vibrant coral, and graceful sea turtles on this 6-hour snorkel excursion to Honolua Bay. Experience one of the island’s most popular snorkel spots with the help of a certified marine naturalist before heading to a second site for more underwater adventure. An included breakfast, barbecue lunch, and periodic sightings of wild dolphins help add to the experience.

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.

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.

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.

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers, unlimited non-alcoholic beverages, and 2 complimentary adult beverages as you cruise around. From December to March, the tour includes a whale watch to see humpback whales and extends by 30 minutes.

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.

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! This charter is a seasonal opportunity, available from December 15th to March 31st annually.

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.

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.

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them too. With a partnership with the award-winning immersive experience “Sounds of the Ocean,” be immersed in the hauntingly beautiful songs of the humpbacks as they echo through the Pacific. For twenty-five unforgettable minutes, everything else fades away and you’re transported into the whales’ world of sound with onboard hydrophone technology and personal headphones. Along the way, expert naturalists will share the classic PacWhale Eco-Adventures experience you love — breathtaking encounters, small group interpretation, and fascinating whale behavior — but with a special focus on the incredible role sound plays in the lives of these ocean giants. Discover how whales communicate, court, navigate, and even share cultural traditions through song. Learn about the growing challenges of noise pollution in the oceans.