11 Open-Bar Cruises in Maui to Plan a Maui Day Around

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

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

Board a barefoot catamaran from Ka’anapali Beach for a roughly two-hour sunset sail. Expect an open bar, substantial pupus, coastal views toward Lanai, Molokai, and Kahoolawe, and possible dolphins or winter whales. The crew handles drinks and safety; beach boarding means you will wade through water, and shoes come off before you board.

“We had a great time on the sunset cruise. The drinks and food were great and plentiful. The crew was fun and kept our drinks full. We plan on doing it again next time we're in Maui!”

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

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

Sail from Ka’anapali Beach for a two-hour humpback whale watch aboard Sea Maui’s catamaran. A trained naturalist explains whale behavior and migration while you scan the West Maui waters from open nets or regular seating. Snacks and unlimited drinks are included. Check in 30 minutes early; beach boarding may be difficult if you have mobility issues.

“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

Set out from Ka'anapali Beach on a two-hour sunset sail aboard a Teralani catamaran. Expect ocean and West Maui Mountain views, an open bar, and pupus such as coconut-crusted shrimp and caprese skewers. You’ll wade through shallow water to board. Humpbacks may appear from November to April, but this is a sunset cruise, not a whale-watching tour.

“Great fun! Captain Julia and First Mates Anna and Nico were fabulous. Felt warmly welcomed, had a wonderful sail with the spectacular sunset and avoided the rain showers. Cocktails and pupus were perfect. Mahalo!”

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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, a Hawaiian-built catamaran, at Maalaea for an approximately two-hour sunset cruise with island-style music, appetizers, and alcoholic and nonalcoholic drinks. The captain and crew take you out along the coast, with possible dolphin sightings and humpback whales from December through April. The boat has two restrooms and a maximum of 40 people.

“Very friendly staff. Amazing experience. Would highly recommend this adventure. Good food and drinks too”

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5.Whale Watching Cruise with Open Bar

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

Sail from Whaler’s Village for a two-hour search for humpback whales, with English-speaking naturalist guides, Kaanapali shoreline views, and an open bar serving cocktails, beer, and wine. Sightings can include mothers and calves, but vary by day. Whale season runs December through April.

“We had a great crew- Travis, Jenny and Mario made it a great time, They served up great drinks and good times. We got to see a lot of whales and even got to hear them. The crew was very fun and it was the highlight of my trip!”

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

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

Sail from Kaanapali aboard a luxury catamaran for two snorkel stops chosen to suit seasonal conditions. Breakfast, snorkel gear, flotation aids, a barbecue lunch and an open bar are included. The crew may vary; Captain Sam, Drew and Mario are among the names associated with past sailings.

“Super fun part of our trip! The crew was awesome and made the day so fun. Food was great and snorkeling was amazing! Definitely will do again on our next visit.”

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7.2 Hour Sunset Dinner Sail with Open Bar and Appetizers

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

Board Gemini from Kaanapali Beach for a two-hour sunset sail with cushioned seating, island-style food, and an open bar serving Mai Tais, local beer, wine, and more. You’ll see the West Maui Mountains and nearby islands from the water. Check in by the Westin’s Ulu Kitchen, and expect to get your feet wet during beach boarding.

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

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

Sail from Ka’anapali on a four-hour catamaran trip, with a crew to help you get set up for snorkeling among Maui’s fish and, if luck is on your side, turtles or dolphins. Breakfast, snorkel gear, a BBQ lunch, and an open bar are included. Crew members have included Captain Ian, Mario, and Sam, though your crew may differ.

“This is by far the best experience we had in Maui. The Kids had the most fun. Mario was extremely friendly and patient with the Kids, answering all their questions, from Snorkeling to technical stuff about the yacht. His crew was a delight to talk to. They made sure everyone on the Yacht was taken care of. They were all multitasking, and it's rare to see this kind of commitment to customer service. I would highly recommend this experience to everyone.”

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9.Kaanapali Whale Watching Boat with Open Bar and Food

★★★★★★★★★★5.0 · 6 reviews · 2h 30m · from $167

Sail from Ka'anapali Beach on a 35-person catamaran for a 2.5-hour humpback whale watch. The crew shares insights as you scan the water, with gourmet pupus and an open bar included. Departures are daily at 12:30 PM, and if no whales are seen, you can join a Classic Whale Watch for free.

“The crew was great and made it extra fun! Cpt Matt and Gavin were especially attentive and enjoyable. It was a perfect day and saw lots of whale activity, so no complaints. Only thing I was missing was jumping in and swimming it was so hot! All around will recommend and do again with future family and visiting friends. Mahalo!”

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

★★★★★★★★★★4.5 · 5 reviews · 2 hours (approx.) · from $141

Teralani Sailing’s two-hour Holo Holo cruise follows Maui’s west coast from Ka’anapali Beach. You’ll have an open bar with beer, wine, champagne and tropical cocktails, plus pupu and dessert. Expect sunset views of West Maui’s mountains from the water, a small group capped at 49, and stairs between the beach and the vessel’s deck.

“What a wonderful experience! From check in to goodbye the staff was so warm and friendly, made us feel safe; helping my mother on and off the boat. They curated a fun atmosphere with their positive vibes, humor, music, yummy food and drinks- and with energetic expertise- we sailed smoothly for a gorgeous sunset and our fabulous captain, she navigated us to breaching whales and flapping tails! What a wonderful way to spend Christmas Eve! Thank you! Highly recommend! ⭐️⭐️⭐️⭐️⭐️”

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11.Brewery and Beach Cruise in a Vintage VW Bus

★★★★★★★★★★3.5 · 3 reviews · 3 hours (approx.) · from $229

Ride in a restored vintage VW bus from The Shops at Wailea to Maui Brewing Company for lunch and an optional beer flight, then continue to Pa'ako Beach for photos and a short break. The small-group tour lasts about three hours and includes water, Maui chips, and a meal. Jay has driven the tour, though your driver may differ.

“We had an amazing time on the Brewery & Beach Cruise . My wife & I were picked up by our driver Jay. He made us feel welcome from the moment he arrived. He had a great knowledge of the island and was a great driver. The VW van is amazing, restored to perfection and embodies the island vibe. We were chauffeured to the Maui Brewing Co. & treated to a delicious lunch. We highly recommend the pork sliders! We then jumped back into the bus and took a scenic drive down the southern Maui coastline to the lava fields. We were treated to complimentary drinks while enjoying the scenic…”

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