7 Sunset Sailing Cruises in Oahu to Get on the Water

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 Beach Sunset Sail

★★★★★★★★★★5.0 · 378 reviews · 1 hour 30 minutes (approx.) · from $70

Sail from Waikiki Beach aboard Ke Kai for about 90 minutes, with Diamond Head, Mamala Bay, music, soft drinks, and alcoholic beverages included. Crew members including Kyle, Johnny, Justin, and Aiden have been praised for their friendly service and fun energy. Expect an upbeat boat ride, ocean spray near the bow, and a party atmosphere more than a quiet sunset cruise.

“Beautiful cruise. Party atmosphere with bar and places to congregate. We enjoyed the sunset and the lights on the shore.”

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4.Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

★★★★★★★★★★5.0 · 277 reviews · 1 hour 30 minutes (approx.) · from $72

Sail from Waikiki Beach aboard the 50-foot Hāwea for about 90 minutes, with one included drink, music, local stories, and views of Diamond Head and the Honolulu coast. Crew members such as Cameron, Dez, and Kapono help create a friendly, relaxed mood. You will board barefoot through shallow surf, so wear shorts and keep bags light.

“All crews are nice and took photos for us. The tour was amazing and definitely would come back next time.”

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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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6.2-Hour Oahu Sunset Catamaran Sail

★★★★★★★★★★5.0 · 122 reviews · 2 hours (approx.) · from $130

Sail from Ko Olina Marina on a 53-foot catamaran for two hours of ocean views, sunset light, complimentary cocktails, soda, juice, shrimp cocktail, and charcuterie. The crew, including names such as Jackie, Ethan, Todd, Brittany, and Captain Tamika on some departures, handles drinks and snacks while you relax offshore.

“We loved our sunset sail. The staff were great, the ship was beautiful and the snacks and drinks were great. I highly recommend this trip to anyone looking for a comfortable and relaxing sunset cruise.”

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7.Sunset Sail Cruise in Waikiki

★★★★★★★★★★4.8 · 6 reviews · 2 hours · from $54Best value

Sail from Kewalo Harbor on a 55-foot, double-decker catamaran for two relaxed hours along Oahu’s coast. You’ll have shaded cabin seating, an open-air upper deck, snacks, nonalcoholic drinks, two restrooms, music, and an underwater viewing room. Bring your own alcohol if you are 21 or older, and arrive 30 minutes early.

“The activity was good except the boat was really rocky and it made us sick”

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