Top 12 Oahu Sailing Trips

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 Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

★★★★★★★★★★4.5 · 2,109 reviews · 2 to 3 hours (approx.) · from $134

Sail from Kewalo Basin to Turtle Canyon aboard the 40-passenger Honu Lani. Snorkel with green sea turtles under crew guidance, then enjoy lunch and drinks on the midday trip. Chris, Natalie, Greta, Joey, and other crew members have earned praise for calm, attentive service.

“Great experience!! Joey and crew did a great job giving us the turtle/snorkeling experience! Hawaii on a catamaran is definitely a must!! Get out there with them and experience this thrilling adventure! The dolphins were also so beautiful! My tik tok will definitely be awesome with these shots! 100% guys!!!”

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3.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

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

Join the Hawea catamaran from the Duke Kahanamoku Statue for a 2.5-hour Waikiki sail and snorkel at Turtle Canyon. You’ll get gear, flotation support, snacks, drinks, and guidance from crew such as Jenna, Julia, Claire, and Kapono. Swimming ability is required, and the group can reach 45 people.

“The crew made this an awesome, safe, and fun experience! The bar onboard was a great bonus after snorkeling :-)”

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4.See Turtles 100% Guaranteed

★★★★★★★★★★5.0 · 1,420 reviews · 2 hours (approx.) · from $49

Join Oahu Catamarans for a two-hour catamaran trip from Honolulu to Turtle Canyon. Swim with Hawaiian green sea turtles and tropical fish while guides such as Lucy, Shannon, and Krash help in the water. The boat carries no more than 28 people, with gear, drinks, snacks, and turtle sightings included.

“Very exhilarating experience - thecrew - Greg, Shannon & Haley - were wonderful!! Would definitely recommend’”

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

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

Sail from Kewalo Harbor to Turtle Canyon for a 2.5-hour guided snorkel with provided gear, certified lifeguards, a secured raft, restrooms, cushioned seating, and a complimentary first drink. Early departures can bring calmer water, sunrise views, and more time with the crew.

“We had a lovely trip as two families together, 9 total people. 4 adults and 5 kids. The crew was great. They made all of us feel comfortable. The experience was exactly as advertised. The right amount of time. We saw lots of cool underwater sea life, enjoyed the boat ride and some cocktails on the way home.”

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6.Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

★★★★★★★★★★5.0 · 836 reviews · 2 hours (approx.) · from $44Best value

Join Oahu Catamarans for a relaxed two-hour sunset sail from Honolulu. Captains such as Krash and Carlos guide the 40-foot catamaran toward Diamond Head, while the crew serves pupus and helps with photos. Bring your own alcoholic drinks if you are 21 or older, and watch Waikiki light up after dark.

“Very relaxed experience and we were out for a long enough time. Refreshments included which was nice. Would definitely recommend!”

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7.Luxury Catamaran Cruise from Oahu

★★★★★★★★★★4.5 · 682 reviews · 2 hours (approx.)

Spend about two hours aboard Makani Catamaran from Kewalo Basin, sailing past Waikiki toward Diamond Head. Choose an afternoon trip with one complimentary drink or a sunset cruise with an island-style buffet and one beverage. Dolphins, turtles, and seasonal whales may appear.

“The catamaran cruise was awesome. The personnel were are friendly and outgoing. We had a wonderful time. The food left something to be desired, but I would recommend this cruise to anyone. We had my three year old grandson with us and he loved it.”

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8.Ko Olina Catamaran Sail and Snorkel with Lunch

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

Spend about three hours aboard a 53-foot catamaran from Ko Olina, with crew-led snorkeling, lunch, three complimentary cocktails for adults, and views of Oahu’s west coast. Waikiki pickup is available as an upgrade, and guides such as Todd, Matt, and Kai are known for attentive service.

“Amazing. Plus the sailing crew was so kind. Views are amazing and the snorkeling was the best. Highly recommend”

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9.Friday Night Fireworks Catamaran Cruise

★★★★★★★★★★4.5 · 610 reviews · 1 hour 45 minutes (approx.) · from $67

Board Pink Sails Waikiki at 6:30 pm for a 1-hour-45-minute Friday cruise from Ala Wai Yacht Harbor. You’ll pass Waikiki and Diamond Head, enjoy music, buy drinks at the cash bar, and watch Hilton Hawaiian Village fireworks from offshore. Captain Jamie and crew members such as Tyler and John have helped create the lively atmosphere.

“It was a wonderful way to spend my birthday and our last night in Hawaii, I had the best time ever. Captain Jamie and his crew Tyler and John were the absolute best, I would highly recommend/”

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10.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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11.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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12.Waikiki 3pm Tradewind Sail – Open Bar Included

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

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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