15 Maui Sailing Tours to Get on the Water

1.From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

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

Set sail from Ma’alaea Harbor aboard the 49-passenger catamaran *‘Alihilani* for two hours in Maui’s Au‘au Channel. Enjoy included drinks and cold hors d’oeuvres while the crew handles the details. Stretch out on the forward trampolines, use the covered seating, and watch for dolphins or humpback whales from December through March.

“The catamaran sunset cruise was amazing from start to finish. The crew was attentive and highly competent. The sunset was breathtaking! I would highly recommend this activity.”

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2.Molokini Snorkel and Performance Sail with Lunch

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

Sail from Ma’alaea Harbor to Molokini on Sail Maui’s fast catamaran, with breakfast, lunch, snorkel gear, drinks, and reef-safe sunscreen included. Captain Greg, Brandon, and the crew have earned praise for friendly service and good sailing. Expect about 1.5 to 2 hours in the water, plus whale watching in season and a chance to help at the helm.

“Catararan was great, crater was awesome and snorkeling was very good. The crew was great-service and interaction with guests. Greg, Lily and Ben were all exceptional. Breakfast, lunch and beverages were very good.”

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

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

Set sail from Mā’alaea Harbor at 7:30 a.m. with Sail Maui for about five hours aboard a catamaran bound for Molokini Crater. You’ll get snorkel gear, flotation, reef-safe sunscreen, breakfast, lunch, coffee, beer, wine, and attentive crew support. Captains and crew members such as Greg, Jeff, Brandon, Micah, and Lucas are praised for making beginners and families feel comfortable.

“What a delightful morning on the water… the Captain and his two crew members were so warm and accommodating. The Catamarran was comfortable and the food served was yummy. The snorkeling was great ❤️ this excursion far exceeded our expectations!”

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4.Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

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

Sail Maui takes you from Maalaea Harbor toward Lanai for reef snorkeling, sea turtles, fish, and possible whales or dolphins. Expect a five-hour catamaran outing with breakfast, buffet lunch, snorkel gear, reef-safe sunscreen, and an open bar. Captains and crew members such as Patrick, Dan, Chase, Ron, James, and Allie have been praised for clear safety guidance and friendly help.

“Captain Ron, James and the rest of the crew did a great job today. My family had a blast and we appreciate them working on Christmas Eve. The food, music and drinks were also wonderful.”

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5.Sunset Sail from Ma’alaea Harbor

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

Spend about two hours sailing from Ma’alaea Harbor aboard the Ocean Spirit, a luxury catamaran limited to 55 people. The crew serves appetizers, coffee, tea, and non-alcoholic drinks while Hawaiian music and sunset views set the mood. Humpback whales may appear in season. Alcohol arrangements have changed, so confirm them before booking.

“The crew was so amazing. Having to serve in crazy wind was impressive but even more they did it with smiles and positive energy.”

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

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

Spend two hours aboard Teralani’s luxury catamaran, boarding directly from Ka'anapali Beach by wading through shallow water. Enjoy premium drinks, pupus, music, and sunset views of the Pacific and West Maui Mountains. From November through April, you may spot humpback whales, though this is not an official whale-watching trip.

“The staff on the boat was very friendly and helpful. The cruise was beautiful and our spot to watch the sunset was perfect. Be aware that you have to walk in the water (2-3 steps) to get in and off the boat. I wish there was a reduced price for adults not drinking alcohol, but otherwise I think it’s a good value for the money.”

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7.Ka’anapali Luxury Sunset Dinner Sail

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

Spend 150 minutes aboard Teralani Sailing Adventures’ luxury catamaran, boarding directly from Ka’anapali Beach. You’ll enjoy a buffet of Hawaiian-inspired dishes, an open bar, live music, and wide views of the West Maui Mountains. Captain Patrick and crew members such as Sammy, Miles, and AJ have earned praise for warm service and helpful wildlife spotting.

“Great experience. Staff was excellent. The boat was beautiful. We saw dolphins, got great sunset pictures and had drinks and food in hand the whole ride. I highly recommend and we are so glad we did this.”

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8.Snorkeling and Sailing Adventure with Buffet Lunch

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

Spend four hours aboard Gemini from Kaanapali, snorkeling at Honolua Bay or another west Maui site, then sailing with a hot buffet and open bar. The crew provides instruction, quality gear, prescription masks, flotation aids, and reef-safe sunscreen. In winter, watch for humpback whales; in summer, keep an eye out for spinner dolphins.

“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 return! It was a great!! We will be bringing the kids”

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9.Ka’anapali Whale Watching Cruise on Luxury Sailboat

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

Board Teralani’s luxury catamaran directly from Ka'anapali Beach for a two-hour whale watch. A marine naturalist explains North Pacific humpback behavior while an underwater hydrophone lets you hear whale songs. Enjoy Kona coffee, tropical juices, snacks, soft drinks, and Pogmosas, with whale sightings guaranteed or you can return free.

“We had a great time whale watching! The crew was knowledgeable and we saw lots of whales. The boat was comfortable with easy access and there were snacks provided. I would recommend this whale tour.”

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10.2 Hour Sunset Dinner Sail with Open Bar and Appetizers

★★★★★★★★★★4.7 · 65 reviews · from $149

Join Gemini Sailing Charters for a two-hour sunset catamaran cruise from Ka'anapali Beach. You’ll board barefoot from the sand, enjoy BBQ chicken, fried rice, cookies, and an open bar, then watch the sun drop behind West Maui with views toward Molokai and Lanai. Crew members such as Kayla and Russell are known for attentive drink service.

“Beautiful boat, nice and helpful crew, lots of fun, good music! Great view of island and sunset!”

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11.Deluxe Whale Watch Sail & Lunch from Ma`alaea Harbor

★★★★★★★★★★5.0 · 33 reviews · 3 hours · from $137

From Maalaea Harbor, you’ll spend 2.5 hours watching humpback whales with a certified Marine Naturalist. Hear whale songs through an underwater hydrophone, look for mothers, calves, breaching whales, and dolphins, then enjoy sliders, island fruit, snacks, drinks, and up to three alcoholic beverages for adults.

“It was amazing tour. We got to see a lot of marine life and increadibly close whails!”

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12.Ma’alaea Catamaran Sunset Sail with Appetizers

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

Board a PWF Eco Adventures catamaran for a 2 to 2.5-hour sunset sail from Maalaea. You will get open-deck seating, island views, unlimited soft drinks and water, plus ahi crostini, prawn cocktails, kalua pork quesadillas, cheese, fruit, and dessert. Bring approved alcohol, since cocktails are not supplied.

“i highly recommend this cruise! it was the most relaxing part of our trip. the staff was great and served us delicious appetizers and drinks. 10/10”

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13.Lahaina: Private Sunset Sailing Trip & West Maui Mountains

★★★★★★★★★★5.0 · 3 reviews · from $1,936 whole boat, up to 6

Set sail from Whalers Village on a private three-hour cruise for up to six people. Captain Eli, Patrick, Phil, or Matthew may guide your evening, with Hawaiian stories, a fruit and cheese platter, soft drinks, and sunset views of the West Maui Mountains. Bring your own alcohol, and expect shallow-water boarding.

“Captain Eli and Phil were awesome and we had an amazing sunset sail! They shared some really cool details about Maui! The fruit and cheese/cracker platter was delicious too. We would highly recommend this and will definitely be back!”

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14.Coral Gardens Coastal Snorkel & Sail

★★★★★★★★★★5.0 · 2 reviews · from $146

Sail from Ma'alaea Harbor through Maui’s Au‘Au Channel, watching for humpback whales before stopping at Coral Gardens. An English-speaking guide leads the trip, with snorkeling gear, reef-safe sunscreen, lunch, and alcoholic and non-alcoholic drinks included. Bring a towel, hat, sunglasses, and swimwear.

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15.Luxury Catamaran Whale Watch & Sail

★★★★★★★★★★5.0 · 2 reviews · 2 hours · from $119

Join Alii Nui Sailing Charters at Maalaea Harbor for a two-hour, whale-focused trip aboard a 65-foot catamaran. Marine naturalists explain humpback behavior while a hydrophone brings live whale songs onboard. Enjoy panoramic decks, shade, local snacks, and an open bar with valid ID for anyone over 21.

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