Top Maui Sailing Tours

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.

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.

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.

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.

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.

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.

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.

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.

Discover the underwater wonderlands off the coast of Maui on a snorkel tour of Turtle Town from Ma‘alaea Harbor. Soak up spectacular views of Hawaii’s coastline from a double-decker catamaran—equipped with a waterslide for extra thrills—before swimming among turtles and tropical fish at snorkel stops renowned for their wealth of wildlife. Lunch is included so you don’t need to pack a picnic.