Under sail · SUNSET SAILING CRUISES IN OAHU

Sunset Sailing Cruises in Oahu: Our 4 Favourites

4 sailing trips  ·  seats from $70 each

These are the 4 sunset sailing cruises in Oahu to put on the shortlist, each with its price, its time on the water and what comes with the seat. Start at the top and work down.

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 Beach Sunset Sail - A 90-minute route along Mamala Bay
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Waikiki Beach Sunset Sail

3.Waikiki Beach Sunset Sail

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

Board Ke Kai at Waikiki Beach for a 90-minute sunset catamaran sail along Mamala Bay. Expect Diamond Head views, music, soft drinks, alcoholic beverages, and a lively crew, including Captain Justin and guides Kyle and Johnny. Sit near the front for the best ocean feel, but bring a towel because spray can reach the nets.

“Great vibe on the trip. Highly recommended. Did the sunset trip all staff on board were super friendly.”

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2-Hour Oahu Sunset Catamaran Sail - Two hours along Oahu’s west coast
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2-Hour Oahu Sunset Catamaran Sail

4.2-Hour Oahu Sunset Catamaran Sail

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

Set out from Ko Olina Marina for a two-hour sunset sail on a 53-foot catamaran. You’ll receive shrimp cocktail, charcuterie, soft drinks, juices, and three complimentary cocktails while the crew serves you along the coast. Captain Tamika, Jackie, Ethan, Todd, and Brittany have all been praised for warm service, though traffic from Waikiki can make the marina tricky to reach on time.

“We happened upon a pod of dolphins which followed us for a long while. The crew was very friendly and helpful.”

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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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