11 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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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. Your captain chooses the day’s snorkel site, with possible turtles, dolphins, or whales, followed by a fresh BBQ lunch and open bar. Crew members including Ian, Mario, Sam, and others are known for warm, capable service.

“Overall, good experience. We picked this one because it was close to our hotel and it was only 4 hours so it wouldn’t take up a big chunk of the day. Everything went smoothly, with great communication from the crew. Tanner, Elena, Kelly and Jake all did a great job with the organization, the food and the drinks. Food was good and well prepared. The open bar is always a plus. The boat took us near Lahaina to a spot that had plenty of turtles which were friendly and would swim right up next to you. Also go to see some dolphins up close. Highly recommend this tour.”

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9.Kaanapali Whale Watching Boat with Open Bar and Food

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

Join Teralani Sailing Adventures at 12:30 PM from Ka'anapali Beach for a 2.5-hour whale watch limited to 35 people. Captain Matt, Gavin, Captain Mario, and the crew share whale behavior insights while you enjoy open-bar drinks, gourmet pupus, and wide viewing decks. Beach loading requires stairs.

“Wonderful whale watching experience! Great food and beverages as well. We saw some amazing whale activity. Comfortable, safe and very relaxing trip. Highly recommend!”

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

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

Join Teralani Sailing for a two-hour sunset sail from Ka’anapali Beach. You’ll cruise Maui’s west coast with an open bar, chef-selected pupus, music, and views of West Maui’s mountains. The captain may also steer toward whale activity when conditions allow. Stairs from the beach reach the vessel.

“Fantastic crew and cruise. Drinks and appetizers were delicious and free flowing. Had the opportunity to see a lot of whales including babies. A perfect way to end the day!”

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11.Brewery and Beach Cruise in a Vintage VW Bus

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

Meet your crew in Wailea, then ride a restored vintage VW bus to Maui Brewing Company for lunch and a beer flight, followed by scenic coastal views and photo time at Pa'ako Beach. The tour lasts about three hours, serves a maximum of four people, and returns to Wailea.

“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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