The 15 Best Sailing Trips on Maui

1.Whale Watching Tour Aboard Power Catamaran

★★★★★★★★★★4.7 · 827 reviews · from $50Our pick

See Maui humpback whales from a spacious catamaran with narration, hydrophone songs, drinks, and two hours on Maalaea Bay.

“This tour was brilliant! We went on this tour at the end of the whale season so weren’t expecting too much activity but we were incredibly lucky, even managing to see two whales breach! There were beers and strong cocktails available for a very cheap price, and all of the staff were very knowledgeable and entertaining.”

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2.Molokini and Turtles Luxury Yacht Snorkel

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

Review of Maui’s Molokini and Turtle Town yacht snorkel, with food, open bar, luxury amenities, costs, weather risks, and booking tips.

“It's definitely worth paying a little more to skip the crowd. There were only about 25 passengers vs 120 on other boats. The crew was great, food good, open bar was fun. Boat beautiful new and clean. The equipment for snorkeling was new and very good too. They offer ginger laced sprite to calm stomachs. Definitely a great trip. We highly recommend this trip and crew!”

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3.West Maui Snorkeling & Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 210 reviews · from $200

Sail from Maalaea to Lanai for clear-water snorkeling, whale watching, island views, breakfast, lunch, and an open bar.

“Wonderful and helpful crew. Awesome trip with great snorkeling. We even had dolphins swimming right along with us. One of our favorites things we did while in Maui”

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

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

See Maui’s humpback whales from the Winona catamaran, with whale songs, snacks, drinks, island music, and views of three islands.

“Things we liked: +The number of whales we came across! - we really lucked out that day and even caught a few jumps and fin slaps from off in the distance +The microphone they lower into the ocean -Listening to the whales singing was amazing! +The option to sit out front on the catamaran nets -you get splashed but the front row view is worth it! +The bag of chips and the drinks they provide -The mai tais were actually really good. +The registration team we spoke to prior to the trip - they were very personable and easy to get a hold of, and they sent over very thorough…”

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5.Snorkeling and Sailing Adventure with Buffet Lunch

★★★★★★★★★★4.8 · 115 reviews · from $172

Sail Maui’s west coast to snorkel with tropical fish and turtles, then enjoy a hot buffet, open bar, and seasonal whale or dolphin spotting.

“Awesome experience with excellent crew. Just the right amount of time to be out on the water too. Would do this again in a heartbeat!”

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6.Turtles & Tacos Luxury Catamaran Snorkel

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

Review of Maui’s Turtles & Tacos catamaran snorkel, with turtles, tacos, open bar, whale sightings, pricing, tips, and honest drawbacks.

“Wonderful time! The crew were all friendly and experienced. The ship was clean and taken care of and the trip was just the right amount of time for a 5 yr old and 7 yr old. Would absolutely recommend!”

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7.Ka’anapali Whale Watching Cruise on Luxury Sailboat

★★★★★★★★★★4.8 · 89 reviews · from $108

Watch Maui humpback whales from a spacious Ka'anapali catamaran with live commentary, hydrophone songs, snacks, and an open bar.

“The crew was attentive to our needs. Friendly and did what was expected for the purpose of the trip”

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8.Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

★★★★★★★★★★4.5 · 87 reviews · 2 hours (approx.) · from $119

Review of Maui’s Winona sunset sail, with whale watching, open bar, Hawaiian snacks, practical tips, value, and honest drawbacks.

“People were great. Sunset was great. Shouldn’t be labeled a sailing experience as the sail was never raised.”

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9.Luxury Catamaran Whale Watch

★★★★★★★★★★5.0 · 66 reviews · 2 hours (approx.) · from $119

Whale-watch from Maalaea Harbor on a roomy luxury catamaran with naturalist talks, hydrophone whale songs, food, and a full bar.

“Excellent customer service, staff was very friendly. Did not see alot of whales or any quite close but the experience was delightful”

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10.Hawaiian Canoe Sailing Experience in Maui

★★★★★★★★★★4.5 · 59 reviews · 2 hours (approx.)

Sail a private Hawaiian outrigger canoe off Wailea, snorkel with turtles, and learn Maui’s history in a relaxed two-hour outing.

“Sage provided a lot of great information about the islands. The trip was relaxing and fun. The snorkeling was great and Brody was helpful pointing out hidden gems. I highly recommend this tour.”

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11.Sunset Dinner Catamaran Cruise With Drinks

★★★★★★★★★★4.8 · 55 reviews · 2h 30m · from $153

Sail Maui’s coast on a 65-foot catamaran with sunset views, an open bar, chef-prepared dinner, and a champagne toast.

“The entire crew was great! They were quick with the drinks and came to us to offer refills, water, and any help with conquering motion sickness.”

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12.Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

★★★★★★★★★★5.0 · 43 reviews · 2 hours 30 minutes (approx.) · from $289

Review of Maui’s adults-only Royal Sunset Dinner Sail, with a five-course meal, open bar, spacious catamaran, and Pacific sunset views.

“Wonderful experience and delicious food! We went on June 10, 2025, and it was the first day for their new menu. I really didn't expect to have good food - I was going more for the view. However, I loved all the dishes. My husband joked with me that he'd never seen me eat so fast! The boat was new and very nice. Lots of seating options. The sunset was incredible, and we got some really good pictures. The whole crew was friendly. I would absolutely do this again.”

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13.Whale Watching Catamaran Cruise with Drinks

★★★★★★★★★★4.7 · 21 reviews · from $69

Watch Maui humpback whales from the Winona catamaran, hear their songs underwater, enjoy drinks, and take in Molokai and Lanai views.

“The crew was great, friendly and helpful. We got free fruit, chips and soft drinks on the boat. The boat was clean and they were available at the restrooms. The trip was flawless and even though it was the very end of the season, we did encounter whales! The crew knew what they were doing and where to find the whales. We had a great time and definitely recommend it!”

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14.Ma’alaea Catamaran Sunset Sail with Appetizers

★★★★★★★★★★4.7 · 16 reviews · 2 hours - 150 minutes · from $137

Sail Maui’s coast at sunset on a comfortable catamaran with island views, fresh appetizers, unlimited soft drinks, and your own approved alcohol.

“Best experience while I was there! Just need better drink mixologists..but, loved the boat, the crew and the ppl on there. Just so relaxing!”

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15.Sunset Sail on a Charming Hawaiin Catamaran

★★★★★★★★★★5.0 · 5 reviews · from $129

Sail Maui’s coast at sunset aboard the intimate Winona catamaran, with whale watching in season, pupu, local drinks, and Aloha spirit.

“sailing for a sunset is a must. We had a great time and it very nice crew. We were happy enough to book for snorkeling with them to Coral Gardens a few days later.”

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