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“Everything was great!! We seen whales! The sun was shining it was a good day. The captain was very friendly and knowledgeable about the whales. The staff were polite and friendly served drinks . We would highly recommend this whale 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“Parasailing in Maui was thrilling and an unforgettable experience! The crew were friendly and incredibly helpful. This was our first time parasailing and the team made it smooth and very safe! Would definitely look at booking again!”
★★★★★★★★★★
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“Captain Brandon and his crew were great. Super friendly, helpful and knowledgeable. Many times they detoured the boat so we could see whales, an amazing extra for our tour to Molokini. The snorkel spot in the crater was great and we got there at a…”
★★★★★★★★★★
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“Absolutely marvelous. Jeff, Brandon, Micah, and Lucas were exceptional with leading, assisting, and guiding us on an incredible excursion to Molokini Crater. We were graced by a mama humpback, her baby, and a pod of dolphins on the way. For an hour, they breached, swam…”
★★★★★★★★★★
214 reviews5 hours (approx.)From $200.00by Sail Maui
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Yearning for an unforgettable adventure?
★ 4.8“This tour was definitely one of the top 2 highlights of our vacation! The crew was amazing and so helpful. Thank you Patrick, Dan, Maloni and Allie. The whole experience was perfect. Sailing, snorkeling and sunshine! A day we will never forget!”
★★★★★★★★★★
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“We really enjoyed our sunset sail. Our all female crew were fun and hard working (I had no idea of the physical exertion required in hoisting the sail). The food was really good and my beer was cold. But the real attraction was nature itself.…”
★★★★★★★★★★
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“Great experience. Saw over ten whales, both mothers with babies and males. We saw them all breaching and diving.”
★★★★★★★★★★
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.
“Amazing and loads of fun. Great music , informative of the reef and able to relax and see turtles , whales, dolphins , and our captain was great! She made sure to turn around and look for the whales , pause and patiently await their…”
★★★★★★★★★★
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 crew is very professional and friendly, and the food and beverage service is top notch. We didn’t see any turtles that day, but the trip and snorkeling was still awesome!”
★★★★★★★★★★
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“The crew was fun and friendly. We had a great time. It was the perfect ending to our Maui trip. It was a relaxing and beautiful evening.”
★★★★★★★★★★
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“I was offended at being booed loudly for getting a nonalcoholic drink! I’ve been sober a long time and can’t imagine I’m the first adult non drinker they’ve had on the cruise. If I was newly sober that would’ve gone much differently and I would’ve…”
★★★★★★★★★★
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“Beautiful boat and amazing area to be out in. The crew were super nice and friendly continuously making sure youre taken care of and having a good time. Loved they offered professional photos as well.”
★★★★★★★★★★
70 reviews2 hours (approx.)From $159.00by Alii Nui Sailing Charters
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