5 Sailing Tours with an Open Bar in Oahu, Best Day First

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

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

Board the Hawaii-built Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and past Diamond Head. Your captain and crew serve a complimentary first drink from the premium bar, with more available for $8. Look for dolphins, and humpback whales from November through May. Shoes are collected before boarding.

“A really wonderful expierence, we did the VIP which we liked to board early and get the free drinks included. Lovely hosts and weather was amazing!”

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2.Waikiki Sunset Cocktail Sail with Open Bar

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

Join Holokai Catamaran for a 90-minute sunset sail from Waikiki. Drinks include wine, champagne, Maui Brewing beers, rum punch, sodas, juices, and the signature Holokai Hooch. Crew members such as Ryan, Chase, Kevin, Kayla, Bridget, and Alec are known for keeping the mood social. Expect barefoot boarding through shallow water and possible spray.

“Beautiful scenery and vibes !! ✨️ Good drinks at open bar !! Very relaxing, smooth ride to see the sunset 😎 🌺🌇”

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3.Waikiki 3pm Tradewind Sail – Open Bar Included

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

Sail from Waikiki for about 90 minutes aboard the Holokai catamaran. You may see Diamond Head Lighthouse, sea turtles, dolphins, or humpback whales in winter. Captains and crew may include Ryan, Mitch, Austin, and Marc. Expect beach boarding, wind, some boat movement, and a relaxed rather than fast-paced cruise.

“Worth it!!! We had 7 people and everyone enjoyed it a lot. Beautiful scenery and people working were so personable!”

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

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Best value

You’ll spend about two hours sailing from Kewalo Basin toward Diamond Head, with time to swim from the catamaran or stay aboard for coastal views. The friendly English-speaking crew serves cocktails for purchase, provides float belts, and keeps the mood relaxed. This is a swim-and-sail outing, not a snorkeling tour.

“Love the all women crew. Very friendly to talk to and very helpful. 10 out of 10 would recommend again. Very worth the money. Great drinks for great price.”

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5.Honolulu Sunset Sail from Kewalo Harbor Including Drinks

★★★★★★★★★★5.0 · 169 reviews · 1 hour 30 minutes (approx.) · from $61

Board the Na Hoku 2 at Kewalo Basin Harbor for a 90-minute sunset sail toward Waikiki. Expect Diamond Head views, included alcoholic and non-alcoholic drinks, music, and a social party-boat mood. Crew members such as Ricki and Jeff have helped make past sailings especially fun, but check your confirmation for the current departure point.

“What a Fun crew we had! They kept us laughing, played great music, the drinks were just as good. They came around and checked on us, helped take pictures if needed. The only downside I might say is my husband doesn’t drink, but drinks non alcohol beer and I wish more activities like these would have that option, it truly is not fun to not feel included on a booze cruise that you are graciously doing with your wife and daughters. The sail it self was gorgeous, the timing was perfect for the peek of the sunset and the glow bouncing off mountains and pacific. The price was very reasonable…”

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