Under sail · SAILING TOURS WITH DRINKS IN OAHU

4 Sailing Tours with Drinks in Oahu to Book

4 sailing trips  ·  seats from $35 each

The good sailing tours with drinks in Oahu fill their decks early in the season. Here are the 4 to book first, what each includes and how they differ.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - A barefoot sail along the Waikiki coast
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

1.Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Top of the fleet

Join the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a barefoot sunset sail along Waikiki and past Diamond Head. Your first premium drink is included, with more available for $8. The crew, including staff such as Viv and Eli, serves drinks while you watch for dolphins, humpback whales from November to May, and changing sunset colors.

“Great experience, great crew, very satisfied. The positive attitude of the crew made for a very enjoyable and relaxing trip. They were very attentive, boat is clean and well kept. They went to extra efforts to see a whale off of Diamond Head and we were successful at capturing whale flukes with a gorgeous sunset in the background”

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Waikiki Sunset Cocktail Sail with Open Bar - Bare feet, sand, and the first splash
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Waikiki Sunset Cocktail Sail with Open Bar

2.Waikiki Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 554 reviews · 1 hour 30 minutes (approx.) · from $84

Set sail from Waikiki aboard the Holokai Catamaran for 90 minutes of sunset views, conversation, and unlimited drinks. Choose wine, champagne, beer, soda, juice, or the signature Holokai Hooch. Crew members including Ryan, Chase, Kevin, Kayla, Bridget, and Alec have been praised for keeping the mood friendly and the bar moving.

“I would definitely recommend thus to everyone, no matter the age! Our entire family loved it! The crew were all extremely friendly and the sunset was beautiful! Will definitely do this again the next time we come back!”

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Waikiki 3pm Tradewind Sail - Open Bar Included - What the 90-minute route actually delivers
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Waikiki 3pm Tradewind Sail – Open Bar Included

3.Waikiki 3pm Tradewind Sail – Open Bar Included

★★★★★★★★★★5.0 · 246 reviews · 1 hour 30 minutes (approx.) · from $53

Set out from Waikiki at 3 p.m. aboard the Holokai catamaran for a relaxed 90-minute sail toward Diamond Head Lighthouse. Expect ocean views, trade winds, and possible sightings of whales, dolphins, and turtles. Crew members including Captain Austin, Ryan, Mitch, and Grace have earned warm praise for friendly service. Boarding is from the beach, so wear easy-off shoes.

“Great experience! We saw a few whales and even some turtles! The drinks package was nice but you can have a great time without it. I went solo and enjoyed it but groups and families also had a great time.”

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Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast - Sailing toward Diamond Head
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Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

4.Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Lowest fare aboard

Leave Waikiki Beach behind on a two-hour catamaran cruise from Kewalo Basin Harbor. Sail toward Diamond Head, watch for turtles, dolphins, fish, and whales, then swim from the boat or stay aboard with a cocktail. The crew keeps things relaxed, and the small-group setting, capped at 47 people, feels far calmer than the beach.

“We had such an amazing experience✨ 100% recommend this for everyone. The crew was amazing and did their best to make sure everyone was safe and satisfied.”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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