7 Drinking Tours on Maui Worth Booking

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 at Ka’anapali Beach for a two-hour sunset sail with unlimited cocktails, soft drinks, and hearty pupus. The crew, including names such as Tommy, Travis, Jenni, and Mario, keeps service lively. Expect island views, possible whales or dolphins, and wet feet during beach loading.

“Best experience solo traveling in Maui! Thank you Sea Maui crew for an unforgettable night! The crew kept the drinks flowing and the vibes going. Shout out to Tommy for being especially attentive to all the guests 😊 Definitely coming back!”

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

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

Join Sea Maui at Ka'anapali Beach for a two-hour whale-watching cruise led by trained naturalists. Look for humpback whales, calves, breaches, and other sea life from a catamaran with open viewing nets, snacks, and unlimited drinks. Captain James, Captain Nick, and whale expert Charlie are among the crew members praised for their attentive service.

“Excellent trip, crew AND fun! Highly recommend you pick this specific trip. The crew was great and knowledgeable. Thanks Sea Maui!”

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

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

Board the Teralani catamaran from Ka'anapali Beach for a two-hour sunset sail with ocean views from every table, premium drinks, and pupus including coconut shrimp and teriyaki meatballs. Crew members such as Captain Ian, Anna, and Patrick have earned praise for warm service, while whales may appear from November through April.

“Such an incredibly fun time! Great food and drinks, awesome music, beautiful views, and very welcoming and friendly crew. Thank you so much for a fantastic evening!”

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

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

Board Winona in Maalaea at 4:30 pm for a roughly two-hour sunset sail along Maui’s coast. You’ll get Hawaiian snacks, local beer, seltzers, cocktails, soft drinks, music, and two restrooms. From December through April, keep watch for humpback whales.

“It was fun for rverone, they allowed you to walk all over the sail boat barefoot, it was a beautiful sunset, we were lucky and seen whales and dolphins”

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5.Whale Watching Cruise with Open Bar

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

Join Sea Maui at Kaanapali Beach for a two-hour whale watch led by English-speaking naturalists. Watch for breaching humpbacks, hear whale song through an underwater microphone, and enjoy mimosas, beer, wine, Bloody Marys, cocktails, and snacks aboard a comfortable catamaran.

“This was a fun whale watch ! Just what we needed !”

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

★★★★★★★★★★4.8 · 73 reviews · from $183

Set out from Ka’anapali on a five-hour catamaran sail with crew members such as Captain Sam, Drew, and Mario. You’ll visit two snorkel sites chosen for seasonal conditions, search for turtles, fish, dolphins, and whales, then enjoy breakfast, a BBQ buffet, and an open bar.

“Crew was excellent!! Experience was awesome. We actually got to sail on the way back. Saw whales and dolphins in addition to snorkelling with fish and turtles. A great excursion. Highly recommend.”

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7.2 Hour Sunset Dinner Sail with Open Bar and Appetizers

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

Join Gemini Sailing Charters at Kaanapali Beach for a two-hour sunset sail with open-bar Mai Tais, local beer, wine, snacks, and island-style BBQ chicken. You’ll cruise past views of the West Maui Mountains, Molokai, and Lanai from a catamaran with cushioned seating in sun or shade.

“Food and drinks were fine. Nothing too exciting but decent enough. Views and experience were excellent. Easy access and low key guides made this a fun trip.”

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