Maui
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“Great fun! learned a lot from the captain and got to see the whales! Don’t skip on the drinks :)”
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827 reviewsFrom $50by Quicksilver Charters
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
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“The people working there were amazing ! They really took care of us, a special hello to Ben”
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224 reviews5 hoursFrom $200by Sail Maui
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 small group tour with captain Greg, Ben and Micah! Everyone was super personable and friendly. Happy to be on a smaller boat with a knowledgeable captain and wonderful crew! Breakfast, lunch and drinks!”
★★★★★★★★★★
214 reviews5 hours (approx.)From $200.00by Sail Maui
Yearning for an unforgettable adventure?
★ 4.8“This was a fantastic trip! The crew were all totally awesome, friendly, helpful, and informative. Snorkeling area was great, boating was fun, drinks and food were plentiful. Would absolutely recommend this trip to anyone.”
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210 reviewsFrom $200by Sail Maui
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“Beautiful sunset. A few whale spottings! Good and filling appetizers! Sorry that they do not have a liquor license yet!!”
★★★★★★★★★★
207 reviewsFrom $151.00by Pacific Whale Foundation
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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194 reviews2 hours 30 minutes (approx.)From $85.00by Makena Coast Charters
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.
“We would recommend to everyone visiting Maui. Amazing value. Unbeatable guides providing unbelievable service!”
★★★★★★★★★★
115 reviewsFrom $172by Gemini Sailing Charters
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“Great service, food and boat. Unlimited free drinks also a bonus! Saw fish, a whale and one giant honey.”
★★★★★★★★★★
103 reviews3 hours (approx.)From $199.00by Alii Nui Sailing Charters
Experience the thrill of sailing with majestic whales in Maalaea. Join us for a midday adventure on the open seas. Book now!
★ 5.0“Lovely crew, attentive service, enjoyed the smaller boat/ smaller group size. We had a large group including two 3 year olds and an infant, and the crew made really relaxing”
★★★★★★★★★★
101 reviews2 hours (approx.)From $100.22by Sail Maui
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“Great staff! We were able to see several whales.. the captain looked for them and directed the catamaran toward them! Very fun cruise”
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97 reviewsFrom $162by Teralani Sailing Adventures
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“Great sunset cruise! Last minute booking and worth every penny! Staff was friendly and very helpful! Would highly recommend!!!”
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87 reviews2 hours (approx.)From $119.00by Makena Coast Charters
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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82 reviews5 hours (approx.)From $206.00by Sail Maui
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“So much fun, food and drinks were great. Amazing crew. The humpback whales were putting on an incredible show.”
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74 reviewsFrom $112.90by Sail Maui
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“The Aliʻi Nui catamaran sunset sail was a highlight of our trip. Captain Jordan and her almost-all-female crew were not only warm and cheerful but also incredibly hard-working and skilled—raising sails and serving with seamless ease. The meal felt authentically local with pulled pork sliders…”
★★★★★★★★★★
70 reviews2 hours (approx.)From $159.00by Alii Nui Sailing Charters
Sunrise above the clouds, whales under the hull; this is how I'd spend every Maui day.