Top Maui Sailing Tours

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.

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.

Embark an unforgettable sunset sail in Maui, leaving from Ka’anapali Beach. As the sun sinks into the gentle waves, leave the details to someone else while you enjoy mai tais, wine, and beer at the open bar, as well as a selection of appetizers. Experience a romantic happy hour at sea with drinks to get your Maui night started in style.

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.

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.

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.

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

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, watch for humpback whales during an extended tour.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Enjoy the ultimate Ma‘alaea premium dinner cruise with a 4-course meal served as the sun dips below the horizon. Sip on included Mai Tais or other beverages while soaking in incredible views of the Pacific, Lana‘i, and Moloka‘i. With only a select number of guests aboard, this cruise delivers an intimate, unforgettable evening.

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.

Board the beautiful and spacious *Pride of Maui* catamaran for a sunset cruise near Molokini crater. Enjoy an open bar including craft beer and blended drinks, plus a generous buffet featuring barbecued ribs, 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.

Experience the magic of a Molokini and Turtle Town on this catamaran snorkeling adventure, where you can swim inside a sunken volcano surrounded by vibrant marine life. Start your day cruising to Molokini Crater, then dive into its pristine waters to explore the coral reef teeming with colorful fish. Depending on the conditions, your next stop may be Turtle Town or Coral Gardens, where you’ll have the chance to search for sea turtles and create lifelong memories in Maui’s dazzling underwater world.

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.