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.
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…”
★★★★★★★★★★
827 reviewsFrom $50by Quicksilver Charters
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Witness the captivating aerial vistas of Maui's stunning landscape from the thrill of parasailing over the pristine Ka'anapali Beach.
★ 5.0“First time paradailing. The staff was very friendly We had 3 other couples with us on the boat and spent around 8-9 minutes up Definitely worth it”
★★★★★★★★★★
295 reviews1 hour (approx.)From $88.67by UFO Parasail Maui
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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😁”
★★★★★★★★★★
224 reviews5 hoursFrom $200by Sail Maui
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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!”
★★★★★★★★★★
214 reviews5 hours (approx.)From $200.00by Sail Maui
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Yearning for an unforgettable adventure?
★ 4.8“Incredible day! Beautiful boat and full service crew. Great food and drinks and plenty of it! The banana bread was fantastic. The crew did everything to make us comfortable and to make sure we had a great time. We had a lovely peaceful sail at…”
★★★★★★★★★★
210 reviewsFrom $200by Sail Maui
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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”
★★★★★★★★★★
207 reviewsFrom $151.00by Pacific Whale Foundation
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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.”
★★★★★★★★★★
194 reviews2 hours 30 minutes (approx.)From $85.00by Makena Coast Charters
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Embark on an unforgettable Maui snorkeling and sailing adventure! Immerse yourself in the vibrant marine world, indulge in a delicious buffet lunch, and create lifelong memories.
“Everything was amazing!! The crew was so cool. We can’t wait to go to Maui.”
★★★★★★★★★★
115 reviewsFrom $172by Gemini Sailing Charters
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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…”
★★★★★★★★★★
103 reviews3 hours (approx.)From $199.00by Alii Nui Sailing Charters
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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.”
★★★★★★★★★★
101 reviews2 hours (approx.)From $100.22by Sail Maui
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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”
★★★★★★★★★★
97 reviewsFrom $162by Teralani Sailing Adventures
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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…”
★★★★★★★★★★
87 reviews2 hours (approx.)From $119.00by Makena Coast Charters
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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.”
★★★★★★★★★★
82 reviews5 hours (approx.)From $206.00by Sail Maui
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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.”
★★★★★★★★★★
74 reviewsFrom $112.90by Sail Maui
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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”
★★★★★★★★★★
70 reviews2 hours (approx.)From $159.00by Alii Nui Sailing Charters
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