15 Sailing Trips on Oahu Worth Booking

1.Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

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

Sail from Kewalo Basin aboard the 40-person Honu Lani, then snorkel with green sea turtles at Turtle Canyon. Guides such as Chris, Natalie, Greta, and JoJo provide safety help in the water. The midday trip includes lunch, beer, wine, and cocktails, while the morning trip includes soft drinks.

“The catamaran was beautiful, the staff was very friendly, accommodating, very knowledgeable and did everything they could to make sure we saw turtles!”

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2.Waikiki Turtle Snorkel and Sail on Hawea Catamaran

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

Meet at the Duke Paoa Kahanamoku Statue for a 2.5-hour Hawea catamaran trip to Turtle Canyon. You’ll snorkel with provided gear, look for Hawaiian green sea turtles, reef fish, octopuses, and starfish, then sail along Waikiki with snacks, drinks, and cold brew from ARVO Café.

“This is a must do! Crew was great, sailing was super chill and a bonus. Will definitely do this again.”

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

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

Set out from Pier A at 1025 Ala Moana Blvd for a two-hour Turtle Canyon snorkel trip. Captain Krash, Kareem, Lucy, Shannon, and crew guide you toward Hawaiian green sea turtles, colorful fish, and possible dolphins or whales. Gear, drinks, snacks, and a maximum of 28 people are included.

“Great friendly funny and knowledgeable guides, saw turtles so many cool fish and dolphins on our ride back!”

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4.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 with Moana Sailing Co. Snorkeling gear, lifeguards, a secured raft, restrooms, cushioned seating, and a complimentary first drink are included. Look for turtles, fish, starfish, octopuses, and possibly dolphins or a monk seal.

“Amazing snorkeling experience for the kids! The crew was extremely professional and wonderful with our girls! We saw four turtles up close and tons of beautiful fish. The crew supervises from the water and you wear a life preserver belt so it’s perfectly safe for beginners. Highly recommended!”

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5.Waikiki Signature Sunset Catamaran Sail

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

Sail from Honolulu toward Diamond Head on a 53-foot catamaran with a bento box, two alcoholic drinks, and unlimited soft drinks. The crew, including captains Chris and Flynn on some departures, shares local wildlife information while you watch for turtles, dolphins, and seasonal whales.

“What a wonderful sunset. The crew and catamaran were top-notch. I definitely would do this again. Very friendly and a perfect way to end our trip to Hawaii! I would recommend this to all.”

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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

Spend about two hours on a 40-foot Oahu catamaran with captains such as Krash or Carlos, enjoying Diamond Head views, sunset colors, pupus, music, and Waikiki after dark. Bring your own beer or wine if you are 21 or older. The cruise carries up to 28 people and returns to Pier A.

“Sushi the dog was brilliant! Lucy the mate was incredible. She was always helping to take pictures or taking plates away or just talking to the guests. She made everyone feel special. Captain was awesome and I swear has an eagle eye as he spotted 2 humpback whales. Beautiful night smooth sailing. I would definitely go again.”

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7.Luxury Catamaran Cruise from Oahu

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

Sail from Kewalo Basin on the Makani, a spacious Honolulu catamaran with afternoon and sunset departures. Expect Waikiki and Diamond Head views, possible dolphins, turtles, or seasonal whales, one complimentary drink, and a buffet dinner on sunset cruises.

“Just OKAY, we went out in the bay, not past Diamond Head, had a few drinks, no whales or any marine life.”

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8.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

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

Spend 2.5 hours aboard Hāwea, Waikiki Sailing Company’s hand-built 50-foot catamaran. Snorkel at Turtle Canyon with green sea turtles and reef fish, then sail past Waikiki and Diamond Head. Crew members including Jenny, Julia, Kaitlyn, and Kaola help you stay safe and spot marine life.

“It was my first time snorkeling so I didn't know what to expect. I absolutely LOVED this tour/activity. The staff was beyond friendly and kind and super attentive they really wanted to make sure we had an enjoyable experience and soaked in every moment we could. it was the highlight of my trip and I would totally recommend Hawea to friends and family if they ever visit waikiki because this is a once in a lifetime opportunity to do!”

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9.Waikiki Deluxe Catamaran Whale Watch

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

Cruise from Kewalo Basin for about two hours on a catamaran or monohull, watching for humpbacks, tail slaps, and breaches. Your crew explains the whales’ migration, serves snacks, drinks, and premium bar options, and provides a return ride if no whales appear.

“We had a great time. Staff were awesome. We actually only had 6 ppl on our 3pm tour. It was giving private charter but that’s random don’t expect that. We saw several whales, tail slaps, pectoral slaps, sprays, and my fav a breach. It was brilliant.”

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10.Ko Olina Catamaran Sail and Snorkel with Lunch

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

Join Captain Todd and the Ko Olina Ocean Adventures crew for a three-hour catamaran sail from Ko Olina. You’ll snorkel with tropical fish, watch for dolphins and whales, then enjoy sandwiches, snacks, three cocktails, juice, and a freshwater shower on the return trip.

“Great tour! Highly recommend. Fabulous crew who work very hard and make sure everyone has a blast! Terrific sea life and an unexpected whale show!”

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11.Friday Night Fireworks Catamaran Cruise

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

Cruise from Ala Wai Yacht Harbor along Waikiki’s coast as the city lights come on and fireworks rise near Hilton Hawaiian Village. The crew, including captains and deckhands such as Jamie, Tyler, and John on some sailings, keeps the mood lively with music, drinks, and coastal views.

“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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12.Waikiki Sunset Catamaran Sail and Swim

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

Join Pink Sails Waikiki for a two-hour afternoon or evening cruise with a friendly English-speaking crew. Expect Diamond Head views, music, Waikiki lights, and time to jump into the ocean before sunset. Boat assignments can change, so the ride may not always use a catamaran.

“The activity itself is fun. We get to swim whilst we were waiting for the sun to set. We even saw a whale! The other tourists i was with were super awesome. Love the vibes. The staffs are friendly, accommodating and just amazing! They made the time out there fun and engaging. Too bad i cant remember their names but i think the captains name was nick. Anyways, to the crew who sailed us on the 6th of February 2005 departing at 1700 for the sunset swim and sail, thank you very much!!! ♡ ♡ ♡ ♡ ♡”

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13.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 along Waikiki. You’ll have open-air and shaded seating, a full bar, light bites, restrooms, and views of Diamond Head and Honolulu. The casual crew, including captains and bartenders such as Clay, Greg, and Mark, keeps the mood easy and social.

“This my favorite tour/activity that my wife and I did while in Waikiki. The drinks were strong and the appetizers were filling. The boat was nice and the crew and captain were so down to earth and fun to be around. Highly recommend!!”

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14.Swim with Dolphins Catamaran with Waterslide & Lunch on Oahu

★★★★★★★★★★4.5 · 166 reviews · 4 hours (approx.) · from $199

Set out from Waiʻanae on a four-hour catamaran trip with Iruka Hawaii Dolphin. You’ll search for wild dolphins, then snorkel at Makaha with turtles and reef fish. Lunch, gear, snacks, hot drinks, paddleboards, kayaks, a floating mat, and a 21-foot waterslide are included. Whale sightings are possible from November to March.

“Hi I got my wish after many years to see dolphins in their natural environment (twice!) and also to see a baby turtle. The trip was good, but not for the fate hearty. I had to go upstairs on the boat as there was quite a few people being sick and due to a large number of non-English speaker on the boat felt a bit excluded (the company was good as their was an interpretar on board). The crew were really on it in more ways than one!”

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15.Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

★★★★★★★★★★5.0 · 157 reviews · 3 hours (approx.) · from $120

Join Blue Ocean Snorkeling for a three-hour Waikiki catamaran outing with turtle snorkeling, kayaking, paddleboarding, sea scooters, and jumping from the boat. The 45-seat catamaran carries gear, snacks, drinks, and two restrooms. Crew members including Dustin and Captain Nate help keep the day safe and easy.

“Confusion with pickup location communication! Great guides! They did drop us back at our hotel🏝️🤿🐠🐠🐠”

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