10 Maui Sailing Trips to Build a Day Around

1.Whale Watching Tour Aboard Power Catamaran

★★★★★★★★★★4.6 · 979 reviews · 2 hours · from $49Our pick

Cruise Maalaea Bay with Quicksilver Charters from December through April. Your captain and crew explain whale behavior while you watch for breaches, tail slaps, spy-hops, mothers, and calves. The double-deck catamaran has open and shaded seating, restrooms, drinks, and underwater hydrophones.

“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 who was at the bar. Also, great!”

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2.Molokini and Turtles Luxury Yacht Snorkel

★★★★★★★★★★5.0 · 477 reviews · 5 hours (approx.) · from $263Top rated

Spend about five hours aboard Pride of Maui’s modern yacht with Captain Justin and crew. Snorkel at Molokini and Turtle Town when conditions allow, then enjoy breakfast, a grilled lunch, warm showers, and an open bar. The boat welcomes ages 8 and up and carries no more than 40 people.

“Awesome boat and crew, but cancelled 2 days in a row due to bad weather. On third day we finally went but never went to Molokini crater or turtle town due to wind and water conditions. Snorkeling was below average in a protected cove along shore.”

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3.‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114

Board Sail Maui’s Alihilani at Maalaea Harbor for a two-hour sunset sail in the Auau Channel. You’ll find cold hors d’oeuvres, drinks, open deck space, forward trampolines, and an English-speaking crew. From December through March, keep watch for humpback whales.

“We really enjoyed our sunset cruise, the crew was fun and attentively engaged with the passengers -checking on & asking if people wanted a drink brought out to the deck. As well as being willing totake pictures. It was my most favorite activity in Maui, because it was so relaxed for my hisband & I- we loved sitting on the net and watching the sunset. Not rushed and a highlight of our vacation!”

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4.Molokini Snorkel and Performance Sail with Lunch

★★★★★★★★★★4.8 · 224 reviews · 5 hours · from $200

Sail Maui takes you from Maalaea Harbor to Molokini on a fast catamaran for a five-hour trip with breakfast, lunch, drinks, snorkeling gear, and reef-safe sunscreen. Expect a small-group feel, clear water, trade-wind sailing when conditions allow, and possible whale sightings from December through May.

“Super well organized and laid back. The crew was super nice and knowledgeable. Sailing was amazing and beautiful. Snorkeling at the Molokini was great (not all trips make it there as it depends on the weather, we did :)). Winds are usually strong and it is a bit rough so be aware. You may not want to do this if you get sea sick. Otherwise, I highly recommend.”

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5.Molokini Snorkel and Performance Sail: Mā’alaea Harbor

★★★★★★★★★★5.0 · 214 reviews · 5 hours (approx.) · from $200

Sail Maui takes you from Mā’alaea Harbor to Molokini Crater aboard a catamaran with snorkel gear, reef-safe sunscreen, breakfast, lunch, beer, wine, and a crew that includes captains and guides such as Greg, Jeff, Brandon, and Micah. Expect about five hours on the water, with whale sightings possible in season.

“Such a nice experience. I don't love touristy boat trips but this team really made the experience nice and treated us like adults. Even took us to an extra location that I'd never been to before which was amazing.”

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6.Sunset Sail from Ma’alaea Harbor

★★★★★★★★★★4.5 · 207 reviews · from $151

Sail aboard the Ocean Spirit catamaran from Ma’alaea Harbor for about two hours. You’ll get island-style music, appetizers, coffee, tea, and non-alcoholic drinks while watching the Pacific sunset. Humpback whales may appear in season. Confirm current alcohol rules before booking.

“Had a delightful sunset cruise recently. The water was calm, sailing was smooth, and the crew was attentive. The drinks were fantastic, and the Hawaiian music set a perfect vibe. While the appetizers were just okay, the overall experience was very enjoyable. No whales spoRead more”

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7.Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

★★★★★★★★★★5.0 · 194 reviews · 2 hours 30 minutes (approx.) · from $85

Sail from Maalaea aboard Winona, Maui’s Hawaiian-built catamaran, for about 2.5 hours of humpback watching from December through March. Captains Sam or Spencer and crew members such as Megan share whale facts, serve snacks and drinks, and use underwater microphones to let you hear whale songs.

“Excellent trip that fulfilled a bucket list item! The crew was incredible. Extremely knowledgeable and patient with questions. They provided excellent insight to the marine life of Maui.”

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8.Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.7 · 150 reviews · 2 hours · from $134

Board Teralani’s luxury catamaran directly from Ka'anapali Beach for a two-hour sunset sail. Enjoy premium drinks, Hawaiian beer, wine, Mai Tais, pupus, and 360-degree views of the Pacific and West Maui Mountains. From November through April, you may also spot humpback whales, though this is not a formal whale watch.

“Fabulous and fun crew. Very safe and lovely tour! Mario and Bree were awesome as was the captain!!!”

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9.Ka’anapali Luxury Sunset Dinner Sail

★★★★★★★★★★4.8 · 123 reviews · 2h 30m · from $169

Spend 150 minutes aboard Teralani’s luxury catamaran, loading directly from Ka’anapali Beach for a sunset sail with buffet dinner, premium drinks, and views of the West Maui Mountains. Crew members such as Captain Patrick and Captain Sam add local insight, while seasonal whale sightings can turn dinner into a wildlife show.

“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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10.Turtles & Tacos Luxury Catamaran Snorkel

★★★★★★★★★★4.5 · 103 reviews · 3 hours (approx.) · from $199

Sail from Maalaea Harbor on a spacious Ali’i Nui catamaran for roughly three hours of turtle snorkeling, tacos, margaritas, and local beer. Captains such as Bre, Josh, and Tim have earned praise for calm, attentive service. Gear, reef-safe sunscreen, showers, and shaded seating are included.

“Great crew, very clean boat, great lunch. The trip was fun and we saw turtles, fish, and whales. Overall a fun three hour trip.”

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