Best Boozy Tours in Maui: Our Top 9

1.Original Sunset Cruise with Open Bar from Ka’anapali Beach

★★★★★★★★★★5.0 · 1,422 reviews · 2 hours (approx.) · from $127Our pick

Board Sea Maui’s barefoot catamaran from Ka’anapali Beach for a two-hour sunset sail with unlimited drinks, hearty pupus, live music on Tuesdays and Thursdays, and seasonal whale watching. Crew members including Jim, Travis, Jenni, Mario, and Tommy are known for attentive service. Expect wet feet and a lively, casual ride.

“We had a great time! The crew was very attentive an brought us drinks as soon as we were done, and gave clear instructions so everything went smoothly! Would definitely do again!”

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2.Whale Watching Cruise with Open Bar from Ka’anapali Beach

★★★★★★★★★★5.0 · 802 reviews · 2 hours (approx.) · from $115

Cruise two hours from Ka’anapali Beach aboard Sea Maui’s catamaran, watching for humpback whales with help from naturalists such as Charlie, Captain James, and Nick. You’ll have open-net seating, snacks, an open bar, and a small group of up to 42 people.

“The staff on this cruise was really great from the very start. We saw whales almost every minute and got to see several breach. At the end of the cruise I wanted to book another. I would go every day with this crew. Nico, “Bob”, and Nick, Thank you for an amazing time!! 🐋”

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3.From Ma’alaea: Maui Sunset Cruise with Drinks and Snacks

★★★★★★★★★★4.8 · 331 reviews · from $103

Join Sail Maui aboard the catamaran *‘Alihilani* for a two-hour sunset sail from Ma’alaea Harbor. Relax on the forward trampolines or under the cabin, enjoy cold hors d’oeuvres and drinks, and watch for dolphins, seabirds, or humpback whales from December through March.

“Absolutely amazing experience! Jamie, Nicholas, and Steven were a fantastic crew, and we would recommend this to anyone coming to Maui!”

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

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

Board Teralani’s luxury catamaran from Ka'anapali Beach for a two-hour sunset sail with oceanfront seating, an open bar, chef-inspired pupus, and views of the West Maui Mountains. From November through April, you may also spot humpback whales, though this is not an official whale-watch trip.

“Great fun. Good mai tais and au d’oevres. Cheers to Israel”

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5.Kaanapali Beach 5-hr Snorkel w/ BBQ Lunch & Open Bar

★★★★★★★★★★4.8 · 116 reviews · 5 hours · from $193

Cruise from Ka’anapali on Teralani’s luxury catamaran, stopping at two snorkel sites chosen for the season. You’ll get breakfast, gear, a grilled BBQ lunch, and an open bar. The crew, including captains such as Mario, Ian, and Patrick, keeps the day friendly and well organized.

“This snorkel activity was the best we could have chosen! Despite not ideal weather conditions, the crew was able to find us 2 perfect spots to snorkel and explore! Through the coral reef with fishies then sea turtles and dolphin siting on the way back in! Captain Sam and crew were a delight! Could not have been a more perfect day!”

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6.Kaanapali: Whale Watching Cruise with Open Bar

★★★★★★★★★★4.9 · 83 reviews · 2 hours · from $103

From Sea Maui’s kiosk at Whaler’s Village, you’ll cruise from Kaanapali Beach with naturalist guides, a premium open bar, and whale-watching time focused on Pacific humpbacks. Crews such as Travis, Jenny, Mario, Em, Bobby, Kyle, and Lanny have led lively outings with whale songs, breaching whales, and family-friendly commentary.

“Wonderful trip, saw lots of whales, boat was fun and drinks were a bonus!”

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7.2 Hour Sunset Dinner Sail with Open Bar and Appetizers

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

Spend two hours sailing from Ka’anapali Beach aboard Gemini, a spacious catamaran with indoor and outdoor seating, a full open bar, island-style BBQ chicken, fried rice, and sunset views toward West Maui, Molokai, and Lanai. Check in by Ulu’s Kitchen at the Westin.

“The whole tour was run so well, the boat was very modern & plenty of room for people to sit and watch the sunset. There seemed to be a lot less people onboard than other tours, and the team were very attentive bring food & drinks throughout so you didn’t have to get up. Would highly recommend!”

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8.Kaanapali Beach 4-hour Snorkel w/ BBQ Lunch & Open Bar

★★★★★★★★★★4.8 · 42 reviews · 4 hours · from $167

Spend four hours aboard Teralani Sailing Adventures’ catamaran from Ka’anapali Beach. Crew members such as Captain Ian, Mario, Sam, and their teams help you snorkel with tropical fish and turtles, then serve breakfast, a BBQ buffet, and drinks on the sail home.

“Fun snorkling cruise with young but skilled crew, lots of fish to see, good real food and drinks. Great music onboard!”

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9.From Maalaea: Whale Watching Catamaran Cruise with Drinks

★★★★★★★★★★4.7 · 26 reviews · 2 hours · from $69Best value

Cruise from Maalaea aboard the small catamaran Winona for two hours of whale watching with a marine biologist, hydrophones, island music, soft drinks, and two adult beverages for guests 21 and older. Humpback season runs from December through March.

“Posádka skvělá, příjemná a ochotná. Na lodi jsme dostali zdarma ovoce, lupínky a nealko nápoje. Loď byla čistá a byly k dispozici u toalety. Cesta proběhla bez chyb a ikdyž byl úplný konec sezony, na velryby jsme narazili! Posádka věděla, co dělá a kde velryby najít. Moc jsme si to užili a rozhodně doporučujeme!”

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