Top 15 Sailing in Oahu

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

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

Spend about two hours sailing from Kewalo Basin Harbor past Waikiki and Diamond Head on the Moana Catamaran, a Hawaii-built boat with an experienced crew. Your first premium drink is included, with more available for $8. Arrive early, bring a light sweater, and remember this is a barefoot sail.

“Crew was great. Experience was great. Some good wind made for a good sail. Even saw two whales. One breached nicely.”

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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 aboard the power catamaran Honu Lani, then snorkel at Turtle Canyon with a guide nearby. You get premium gear, flotation devices, and a chance to see turtles, reef fish, dolphins, or seasonal whales. Midday trips include lunch, beer, cocktails, and wine. Crew names vary, with Chris, Natalie, Greta, and Joey among those recently working tours.

“Great experience! The crew was very experienced and made sure we all felt safe and secure. They were very knowledgeable and made out adventure that much more intriguing.”

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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

Sail from Waikiki to Turtle Canyon aboard the Hawea catamaran, where you can snorkel above a shallow reef with Hawaiian green sea turtles, tropical fish, octopuses, and starfish. Your crew provides gear, snacks, soda, and cold brew from ARVO Café. Choose a morning or afternoon departure, then return under sail.

“The boat is top notch, as were the crew! I’ve been on many a catamaran snorkel adventure and this was one of my favorite!”

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4.Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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

Join Oahu Catamarans for a two-hour Turtle Canyon trip from Honolulu. Captain Krash, Kareem, Lucy, Shannon, Holly, and the crew guide you toward Hawaiian green sea turtles, tropical fish, and possible dolphins or whales. Gear, refreshments, and onboard safety support are included. Sushi, the captain’s dog, may also come along.

“Super fun tour! Plenty of sea turtles and other fish. The water was clear, the guides are very friendly and knowledgeable. A must-do experience in Hawaii”

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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 guided family snorkeling trip with provided gear, lifeguards, and a secured raft for children and beginners. Look for turtles, fish, octopuses, starfish, and dolphins, then enjoy a complimentary first drink at the full bar while cruising back toward Waikīkī and Diamond Head.

“The experience was amazing . The sea turtles are placid creatures & so wonderful to see up close swimming”

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6.Waikiki Signature Sunset Catamaran Sail

★★★★★★★★★★4.5 · 890 reviews · 1 hour 30 minutes (approx.) · from $89

Board Hawaii Nautical’s 53-foot catamaran in Honolulu for a 90-minute barefoot sunset cruise along Waikiki toward Diamond Head. You’ll receive a light bento box, two alcoholic drinks, and unlimited nonalcoholic beverages. Crew members such as Chris, Phil, and Keoni have been praised for their friendly service and wildlife tips.

“This sunset sail (with adult beverages) was the best kick-off for our Oahu vacation. Sailing turned travel stress into laid-back bliss. When we get our own catamaran, we will hire this perfect (Joey+Andrea+?) crew!!”

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

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

Spend about two hours on a 40-foot catamaran sailing from Ala Moana toward Diamond Head and Waikiki. Captain Krash, Captain Carlos, Shannon, Lucy, Holly, and other crew members have hosted this relaxed cruise, sometimes with the friendly dogs Sushi and Mona aboard. Expect sunset views, light pupus, music, and BYOB for guests over 21.

“We left on time , got a cooler to use , Had some snacks and appetizers,fruits and veggies and humus with pita chips , cheese charcuterie and crackers ready right at the beginning of the trip I enjoyed the choice of music that was themed and well picked - 80-it's , 90ies , Abba etc. Love it ! Thanknyou!”

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8.Luxury Catamaran Cruise from Oahu

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

Cruise from Kewalo Basin along Oahu’s south coast aboard the Makani Catamaran, with views of Waikiki and Diamond Head. Choose an afternoon or sunset departure, watch for dolphins, turtles, and seasonal whales, and enjoy one complimentary beverage. Sunset sailings add an island-style buffet, skyline views, and Friday fireworks.

“I had a great time enjoying the view and the lull of the ocean. My friend didn't think the boat was fast enough. She didn't seem to get that we were there to enjoy the view not race past everything!”

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9.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

★★★★★★★★★★4.7 · 656 reviews · 2h 30m · from $84

Spend 150 minutes aboard Hāwea, Waikiki Sailing Company’s hand-built 50-foot catamaran. Snorkel at Turtle Canyon with green sea turtles and reef fish, guided by crew members such as Jenny, Julia, Kaitlyn, and Kaola, then sail along Waikiki with Diamond Head views. Morning trips include cold brew and granola.

“Loved the activity, guides found the best spot for turtles and saw loads of other ocean life too! Everyone on the boat was friendly and had a great sense of humour which made the trip even better. Fab snorkels and flippers. Nice boat and would highly recommend, worth the price!”

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10.Waikiki Deluxe Catamaran Whale Watch

★★★★★★★★★★4.5 · 638 reviews · 2 hours (approx.) · from $89

Cruise from Kewalo Basin for about two hours as the crew searches for humpback whales in Oahu waters. Captains and guides such as Chris, Joey, Mikey, Keoni, Phil, Finn, Haley, and Clay have led highly praised outings. Enjoy shaded seating, open-air views, snacks, soft drinks, and a full bar. A no-whale trip earns a return voucher.

“We took the boat twice in two days. The first day we didn’t see any whales but had some amazing beverages on the boat. We got a certificate to come back and we returned the next day and saw whales and had more beverages. Capt Joey and crew did a great job.”

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11.Ko Olina Catamaran Sail and Snorkel with Lunch

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

Sail from Ko Olina Marina on a 53-foot catamaran with an attentive crew, snorkel among tropical fish, and watch for dolphins, turtles, and seasonal whales. Lunch, three complimentary cocktails for adults, juice, and soda are included. Waikiki pickup is available as an upgrade.

“The crew was very helpful and friendly from start to finish, making sure everyone had what they needed to have a good time. The catamaran was also well kept and clean. Plenty of room for people to spread out and enjoy the sail to the snorkeling spot and the time int he water. Was a great experience from even as a solo traveler with a spare day to fill.”

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12.Friday Night Fireworks Catamaran Cruise

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

Sail from Ala Wai Yacht Harbor at 6:30 pm for a 1-hour-45-minute catamaran ride along Waikiki. You’ll see Diamond Head, Honolulu’s evening lights, and the Hilton fireworks from offshore, with music, complimentary snacks when available, and a cash bar. Crews have included Jamie, Tyler, John, Bryan, and others, though lineups vary.

“Had a great time with captain Jamie, big Mike and Tyler. Very friendly crew, clean and comfortable boat. Pulled us into an amazing spot to watch the fire works. 10/10 would go again Thanks guys”

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13.Waikiki Sunset Cocktail Sail with Open Bar

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

Join Holokai Catamaran in Waikiki for a 90-minute sunset sail with unlimited drinks, including the Holokai Hooch, champagne, wine, Maui Brewing beer, cocktails, and soft drinks. You board barefoot through shallow tidal water, so bring a towel and wear shoes you can remove easily. Friday sails are for ages 21 and up.

“Great time! Better than expected. Captain Ryan was great as was Alec. Seas were really rough but it wasn’t a problem”

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14.Waikiki Sunset Catamaran Sail and Swim

★★★★★★★★★★4.7 · 519 reviews · from $44

Join Pink Sails Waikiki for a two-hour sunset outing from Waikiki. You’ll cruise past Diamond Head, watch the shoreline light up, and usually get time to swim in the ocean before sunset. Crews have included Jamie, Alex, John, Tyler, Peter, and Ben. The boat may change with weather, repairs, or availability, so confirm what vessel is operating.

“Amazing crew and overall experience. However, it is not a sailboat.”

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15.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, Waikiki’s shoreline, sunset views, music, soft drinks, and alcoholic beverages. Crew members including Kyle, Johnny, Aiden, and Captain Justin have earned praise for friendly service. Expect a lively party-boat mood, and bring a towel or accept getting wet near the front.

“Convenient location and length of cruise! Fun crew, pleasant staff More cocktail variety needed! Mai tai ok”

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