6 Sailing Trips off Waikiki Worth Booking

1.Turtle Snorkeling and Sailing on Hāwea

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

Sail from the Duke Kahanamoku Statue to Turtle Canyon aboard Hāwea, a 50-foot catamaran built by its owner. Snorkel with green sea turtles and reef fish, then relax under sail with Waikiki and Diamond Head in view. Morning trips include cold brew and granola.

“This was one of the best activities we did during our stay here on Oahu! The crew was professional, informed, and friendly. We walked from our hotel, they picked everyone up beachside behind Dukes statue. So easy! We saw 20+ sea turtles, schools of fish, and the sailing at the end was so beautiful. If we come back, we’d definitely consider doing this again with Hāwea!”

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2.Waikiki Sunset Catamaran Sail and Swim

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

Join Pink Sails Waikiki for a two-hour sunset outing from Waikiki. You’ll cruise past Diamond Head, watch the shoreline light up, and may jump into the ocean before sunset. Crews have included Jaime, Alex, John, Peter, and others. Boat type and departure time can change with weather and availability.

“This was honestly one of the best experiences I’ve ever had, and for the price it’s a no-brained. Our crew of Jamie, Peter, and Ben made this sail unforgettable for my group! And they went above and beyond: when my sunglasses fell into the ocean, both Peter and Ben were quick to get their goggles on and jump in to find them. I didn’t think they would be recovered, but they were and for that this crew deserves nothing but high praise from me! They’re energetic, outgoing, and funny. Oh, and can’t forget about the views of the sunset: it was a beautiful backdrop. Take Pink Sails, you won’t regret…”

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3.90 Minute Catamaran Sunset Sail

★★★★★★★★★★4.8 · 64 reviews · 1h 30m · from $56

Join the 45-foot yellow-and-red Na Hoku 2 at Kewalo Basin Harbor for a lively 90-minute sunset sail. You’ll see Waikiki, Ala Moana Beach, Kaka’ako, and Honolulu’s skyline while enjoying soda, juice, water, beer, Mai Tais, and mixed drinks. Expect music, friendly crew, and a social bar atmosphere.

“The sunset catamaran sailing experience was absolutely brilliant. The crew were amazing and very entertaining and made sure everyone had a great time. I thoroughly recommend this to everyone.”

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4.Sunset sailing in small intimate groups

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $103Top rated

Join Captain Tony aboard The Universe for a two-hour sunset sail from Honolulu’s Ala Wai Boat Harbor. The small six-person group keeps the outing personal as you pass Waikiki and Diamond Head, with snacks, drinks, music, restrooms, and space to bring your own food and alcohol.

“Fabulous tour on the water with Captain Tony. Wonderful recommendations, photos taken, and amazing sunset! Thank you Tony!”

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5.Waikiki Friday Night Fireworks Catamaran (Wahine Koa)

★★★★★★★★★★3.3 · 3 reviews · 2 hours · from $84

Join Pink Sails Waikiki for a two-hour Friday night catamaran cruise from Ala Wai Boat Harbor. Choose a 55-foot sailing catamaran or 65-foot power catamaran, enjoy Waikiki and Diamond Head views, and watch the fireworks from offshore.

“Horrible experience.. captain not only asked for tips but also told us how much...and hire an IT GUY.. WE received a cancelation notice even though the trip wasn't cancelled......very unprofessional ..”

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6.Sunset Swim & Sailing Experience

★★★★★★★★★★4.5 · 3 reviews · 2 hours · from $86

Meet the Three Tiki Sailing crew at Ala Wai Harbor for a two-hour BYOB cruise aboard Hokulani. Swim near Diamond Head, then sail into the Pacific sunset with open views, island music, bottled water, onboard restrooms, and room to relax.

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