Under sail · OAHU SAILING TOURS

The 11 Best Oahu Sailing Tours

11 sailing trips  ·  seats from $35 each

Sunset runs, swim stops and full days at anchor. These 11 are the sails in Oahu worth the booking, compared on the details that matter once you are aboard.

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 Turtle Snorkel and Sail on Hawea Catamaran - A simple Waikiki start at the Duke Kahanamoku statue
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Waikiki Turtle Snorkel and Sail on Hawea Catamaran

2.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

★★★★★★★★★★5.0 · 1,655 reviews · 2 hours 30 minutes (approx.) · from $89

Meet at the Duke Paoa Kahanamoku Statue for a 2.5-hour catamaran trip to Turtle Canyon. Snorkel with green sea turtles, tropical fish, octopuses, and reef life in relatively shallow water, then sail along Waikiki. Guides such as Jenna, Julia, Claire, and Dez have been praised for attentive safety help, though you must know how to swim.

“Awesome trip with great sea life including whales, dolphins and sea turtles. The captain and staff were terrific and made sure everyone had a good time.”

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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - Why this works for first-time snorkelers
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

3.Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

★★★★★★★★★★4.5 · 936 reviews · 2 hours 30 minutes (approx.) · from $76

Sail from Kewalo Basin Harbor to Turtle Canyon for a guided snorkel with provided gear, lifeguards, and a secured raft for beginners and children. You may see turtles, tropical fish, octopuses, starfish, dolphins, or even a monk seal. The 2.5-hour trip ends with a complimentary first drink from the full bar.

“We had a great time. The staff was very nice and courteous. Water was beautiful, so relaxing so worth it.”

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Ko Olina Catamaran Sail and Snorkel with Lunch - Sailing along Oahu’s west coast
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Ko Olina Catamaran Sail and Snorkel with Lunch

4.Ko Olina Catamaran Sail and Snorkel with Lunch

★★★★★★★★★★5.0 · 630 reviews · 3 hours (approx.) · from $195

Set out from Ko Olina Marina on a 53-foot catamaran for a three-hour sail, reef snorkeling, lunch, and drinks. Crew members such as Captain Todd, Matt, and Kai are known for attentive help in the water and on deck. You may spot spinner dolphins, sea turtles, whales, and tropical fish. Waikiki pickup is available as an upgrade.

“The experience was great. The family really enjoyed it. We saw lots of species of tropical fish. Make sure you grab food for the fish.”

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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

5.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

6.Waikiki Beach Sunset Sail

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

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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West Oahu Dolphin Watch and Snorkel Sail with Lunch - The ride from Makaha to Makua
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West Oahu Dolphin Watch and Snorkel Sail with Lunch

7.West Oahu Dolphin Watch and Snorkel Sail with Lunch

★★★★★★★★★★4.5 · 320 reviews · 3 hours (approx.) · from $125

Sail Oahu’s Leeward Coast on a catamaran with Hawaii Nautical, watching for spinner dolphins, turtles, and seasonal whales before snorkeling at a calm reef. You’ll get sanitized gear, lunch, a premium bar, shaded seating, and hotel pickup for an added fee. Crew members such as Jesse, Ian, and Caden are known for warm, family-friendly service.

“Awesome beautiful day! Everyone was so nice and helpful. Saw lots of dolphins. Would highly recommend.”

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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

8.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

9.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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Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran - Waikiki from the water, with Diamond Head ahead
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Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

10.Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

★★★★★★★★★★5.0 · 134 reviews · 1 hour 30 minutes (approx.) · from $55

Board the 50-foot Hāwea at the Duke Kahanamoku Statue for a 90-minute afternoon sail toward Diamond Head. Expect Waikiki views, music, made-to-order alcoholic drinks and mocktails, and a friendly crew. Captains and crew members such as Woody, Julia, Dez, and Jenna have helped make recent sails especially welcoming.

“We loved every minute of it!captain was excellent, very professional, and well attentive to all our needs. Drinks were very nice!”

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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

11.2-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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