The 4 Sailing Trips with an Open Bar in Oahu That Earn Their Price

1.Moana’s Sunset Cocktail Sail

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $89Our pick

Set sail from Kewalo Basin Harbor for two hours along Waikiki and past Diamond Head. The Moana Catamaran offers a barefoot cruise, a premium full bar with your first drink included, and a chance to spot dolphins or humpback whales. Crew members such as Vivian help keep the mood warm and relaxed.

“The crew were very attentive and made the trip enjoyable despite the rough seas and some people suffering from sea sickness. Drinks were plentiful with a good variety.”

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2.Waikiki Sunset Cocktail Sail with Open Bar

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

Board the Holokai Catamaran from Waikiki for a 90-minute sunset sail with unlimited drinks, including Maui Brewing beer, wine, champagne, rum punch, and the signature Holokai Hooch. Expect barefoot beach boarding, ocean views, a social crowd, and crew members such as Ryan, Chase, Kevin, Alec, Kayla, and Bridget.

“Every time I come to Hawaii I alway ensure I do this fun experience. I highly recommend it. All the staff are friendly, helpful & very hospitable. A definite 10/10 every time.”

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3.Waikiki Sunset Catamaran Cocktail Cruise

★★★★★★★★★★4.7 · 348 reviews · 1h 30m · from $99

Board the Hanu Lani at Kewalo Basin Harbor for a 90-minute sunset sail past Waikiki and Diamond Head. You get a full bar, snacks, shaded and open-air seating, restrooms, and an English-speaking crew. Arrive early for parking and bring a light layer for the trade winds.

“This was just a fantastic sunset cruise! The boat was the perfect size, the crew was amazing and the views were spectacular. The captain kept us out a little longer so we could enjoy the full sunset.”

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4.Waikiki 3pm Tradewind Sail – Open Bar Included

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

Sail for 90 minutes from Waikiki aboard Holokai’s catamaran, riding the afternoon tradewinds toward Diamond Head Lighthouse. Expect beach boarding, ocean views, possible turtles, dolphins, or winter whales, and a relaxed crew-led outing. Drinks are available, but confirm the open-bar details before booking.

“We got there on time, and the guy on the boat waved for us and left us. I talk to them after and see if they can give us another time or we get our refund but they said no.”

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