Maui

15 Best Maui Sailing & Catamaran Tours

Sailing is Maui showing off, and these are the catamaran trips I’d pick for snorkeling, whales, or plain wind in the sails. Several load right off the sand at Kaanapali Beach; you wade in, climb the ladder, and go. Afternoon departures catch true trade-wind sailing instead of motoring.

1.Ma’alaea Harbor: Whale Watching Catamaran Cruise

On a journey like no other, discover the ocean's secrets with Ma'alaea Harbor's Whale Watching Catamaran Cruise.

Most Popular★ 4.7

“The tour was wonderful! We saw so many whales. Worth the $$. Dave was amazing and super attentive. The Captain (forgot his name but an Aussie and fr New Zealand) was very informative and the perfect host. There was a 3rd gentleman on the tour…”

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3.Maui: Molokini Snorkel and Performance Sail With Lunch

Discover the ultimate adventure in Maui! Snorkel at Molokini, sail like a pro, and indulge in a delicious lunch. Click now for an unforgettable experience!

★ 4.8

“It was such a great experience! Nice small boat, with few people on made it better. The food they had was delicious, breakfast and lunch included and free drinks after snorkeling was just what we needed😁”

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4.Molokini Snorkel and Performance Sail From Maalaea Harbor

Lose yourself in the vibrant underwater world of Molokini Crater during a thrilling snorkel and sail adventure from Maalaea Harbor, where more surprises await.

★ 5.0

“Great experience. Boat was nice, captain and mates were awesome and super friendly. They served breakfast and lunch on board which were both good. Provided good snorkel gear. Would def use them again!”

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6.Sunset Sail From Maalaea Harbor

Experience the magic of a sunset sail from Maalaea Harbor. Set sail on the shimmering waters and witness breathtaking views as the sun dips below the horizon.

★ 4.5

“Fun and beautiful sunset cruise. We saw lots of whales. The captain and crew were great. Informative and entertaining”

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7.From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran

Witness the enchanting songs of whales and the breathtaking views of Maui's coastline aboard the renowned Winona Catamaran, a tour that promises an unforgettable adventure.

★ 5.0

“A lovely experience, many whales.... good, knowledgable crew. A bit hard to find the boat- could use better signage.... No need for music, but good song list - they turned down some when whales were close so we could hear them.”

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9.Turtles & Tacos Luxury Catamaran Snorkel

Adventure awaits on the Turtles & Tacos Luxury Catamaran Snorkel, where vibrant marine life and gourmet tacos promise an unforgettable experience—discover what surprises lie beneath the waves.

★ 4.5

“The boat was really nice, and the crew and captain (Josh) were excellent! They knew exactly where to go to see green sea turtles and an abundance of tropical fish. The service was top, and the food was really good as well. Definitely recommend this…”

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10.Midday Sail With the Whales Maalaea

Experience the thrill of sailing with majestic whales in Maalaea. Join us for a midday adventure on the open seas. Book now!

★ 5.0

“Great environment, crew was fun & made sure we always had a drink in our hand. Saw many whales this trip which made the experience even better. Highly recommend this company to sail with.”

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11.Maui: Sunset Dinner Sail in Ka’anapali

Experience the ultimate romantic evening on a sunset dinner sail in Maui's stunning Ka'anapali. Indulge in delectable cuisine while watching the sun melt into the horizon.

★ 4.6

“It was absolutely fantastic! The sunset was beautiful. We did not see any whales breach but we got to see some whales. The meal was great Good music and good appetizers”

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12.Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

Just imagine setting sail on a charming Hawaiian catamaran, sipping complimentary drinks as the sun dips below the horizon, creating a breathtaking display.

★ 4.5

“It was lovely, just what we expected… We had a little trouble finding the catamaran, Wynonna , as the pin 📍 didn’t work.. It was very windy, food was good, drinks were great,, turned out to be quite spiritual as I met a nice lady…”

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13.West Maui Snorkel & Sail From Maalaea Harbor

Captivating marine life, breathtaking vistas, and a chance to immerse yourself in the vibrant coral reefs of West Maui await you on this unforgettable snorkel and sail adventure.

★ 5.0

“They took us out despite 15 people canceling last minute. We felt like we had rented a charter. Boat was beautiful and the staff was excellent. Even saw some turtles.”

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14.Alihilani Sunset Sail From Maalaea Harbor

Glide across Maui's waters aboard the Alihilani catamaran, soaking up stunning coastal vistas and the chance to spot majestic humpback whales during the enchanting sunset sail.

★ 5.0

“My family and I had a great time! The staff was very friendly and helpful. We caught a beautiful sunset along with some snacks and drinks.”

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15.Alii Nui Makani Cocktail Sunset Sail

Set sail on the Alii Nui Makani Cocktail Sunset Sail and be swept away by a mesmerizing experience that will leave you craving for more.

★ 4.5

“What a wonderful way to end a trip to Maui. A beautiful Catamaran. Delicious sushi and incredible drinks. The Captain and crew were top notch. Highly recommend”

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