Hawaii · SAILING

15 Sailing Trips in Hawaiʻi, Compared

54 tours  ·  from $23

The good sailing trips sell out weeks ahead and the best ones go first. Below: the 15 to book early, what each includes and where they differ.

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - Leaving Honokohau Marina for the Kona coast
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Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

1.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85Our pick

Meet Hang Loose Boat Tours at Honokohau Marina for a four-hour catamaran trip to Kealakekua Bay. You will cruise the volcanic Kona coast, hear about Captain Cook and Hawaiian royalty, snorkel with provided gear, and enjoy lunch aboard. Captains Aiden or Bryce and crew members such as Jordan and Kiwami may lead the trip, depending on availability.

“Great excursion. Would highly recommend it. it was a nice lunch.. Great crew. Very patient waiting for the dolphins and whales.”

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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - What the two-hour route actually gives you
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Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

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

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

Board the Moana Catamaran at Kewalo Basin Harbor for a two-hour sunset sail along Waikiki and beyond Diamond Head. Your captain and crew serve a complimentary first premium drink, with more available for $8. Keep watch for dolphins, seasonal humpback whales, and sunset colors over Honolulu. Shoes are collected before boarding, so expect a relaxed barefoot sail.

“Everyone on staff was very friendly and attentive, offered to take pics without even asking! highly rec!”

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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - The ride past Waikiki and Diamond Head
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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

3.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. You’ll receive premium snorkel gear, a safety briefing, and guided time in the water with green sea turtles. The midday trip includes a deli lunch, beer, wine, and cocktails. Crew members may include Captain Chris, Natalie, Greta, Joey, or Whitney.

“Great crew, great views of diamond head and waikiki, great refreshments, awesome snorkeling, saw 5-6 sea turtles, gliding, surfacing, great fun..”

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Waikiki Turtle Snorkel and Sail on Hawea Catamaran - The Hawea catamaran ride out
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Waikiki Turtle Snorkel and Sail on Hawea Catamaran

4.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 Hawea catamaran trip to Turtle Canyon. Your crew provides snorkel gear, flotation equipment, snacks, soda, and cold brew from ARVO Café. Expect shallow reef water, green sea turtles, tropical fish, and a relaxed sail back toward Waikiki.

“The crew of Hawea was very friendly and knowledgeable. We saw whales for the first time today as well as dolphins and sea turtles. Love the fact that pickup is on fhe beach and happened to be directly across from my hotel. I would definitely book again!”

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Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed - What happens at Turtle Canyon Reef
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Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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

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

Cruise from Waikiki to Turtle Canyon on a roomy catamaran limited to 28 passengers. Swim with Hawaiian green sea turtles and tropical fish while crew members such as Lucy, Shannon, Krash, and Holly guide you in the water. Gear, drinks, snacks, and a return trip to the marina are included.

“Krash, Holly, and Sushi were amazing! Would 100 do again. We even saw a humpback whale fluke! We loved our morning!”

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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Boarding at Maalaea Harbor
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Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

6.Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

★★★★★★★★★★4.6 · 979 reviews · 2 hours · from $49

Cruise Maui’s Ma'alaea Bay aboard Quicksilver’s double-deck power catamaran during humpback season. Captain Kiwi, Captain Carlos, and other crew members provide lively English narration while hydrophones pick up whale songs. You get shaded seating, open decks, restrooms, and drinks, with frequent chances to see calves, breaches, tail slaps, and spy-hops.

“Well worth the reasonable ticket price. Complementary beverages included, and we saw dozens of whales.”

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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - Reaching Turtle Canyon
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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

7.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 2.5-hour guided snorkel with Moana Sailing Co. Your crew provides gear, water guidance, rescue boards, and a secured raft for beginners and children. Look for turtles, fish, octopuses, starfish, and dolphins, then enjoy a complimentary first drink on the ride home.

“Seeing the sea turtles and all the different types of fish. The beautiful blue water. The crew was excellent 👌 We will definitely book again and highly recommend them. It was a great experience for my family and I.”

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Waikiki Signature Sunset Catamaran Sail - Waikiki Coast Views and Possible Wildlife
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Waikiki Signature Sunset Catamaran Sail

8.Waikiki Signature Sunset Catamaran Sail

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

Set sail from Honolulu on a roomy 53-foot catamaran, heading along Waikiki toward Diamond Head for sunset. You’ll get light bites, two alcoholic drinks, unlimited nonalcoholic drinks, and a restroom onboard. The crew, including names such as Chris, Phil, Keoni, and Andrea, keeps the 90-minute cruise relaxed and social.

“This was an AMAZING adventure! The captain and crew were fun, funny, informative... just great. I HIGHLY recommend this tour!”

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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB - Sunset, city lights, and the best seat on board
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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

9.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 catamaran with Captain Krash and a friendly crew, watching the sun set behind Waikiki and Diamond Head. Enjoy pupus, beverages, music, and views of the city lights. Guests 21 and older may bring their own alcohol. The cruise carries up to 28 people and returns to Pier A.

“Captain Krash and his crew (Anna and pups Sushi and Mona) were exceptional! They did a great job to not overbook giving plenty of room on the boat. This trip was laid back and light snacks were wonderful. And the views, stunning! Highly recommend!”

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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Boarding at Kailua Pier and breakfast on the way out
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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

10.Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

★★★★★★★★★★5.0 · 797 reviews · 4 hours 30 minutes (approx.) · from $183

Cruise from Kailua Pier along Kona’s Gold Coast aboard Body Glove’s roomy catamaran. You’ll get breakfast, lunch, gear, reef-safe sunscreen, about two hours at Red Hill, and access to a 20-foot slide and 15-foot jump platform. Dolphins and whales are possible, but snorkeling conditions can vary.

“My wife got sick before the trip and I canceled ahead of time. They did not offer a refund despite my advanced notice. As a Hawaii resident, I’ll never book with them again.”

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Afternoon Sail & Snorkel to the Captain Cook Monument - Entering the sacred waters of Kealakekua Bay
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Afternoon Sail & Snorkel to the Captain Cook Monument

11.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

From Keauhou Bay, you’ll cruise the Kona coast to Kealakekua Bay for about an hour of guided snorkeling near the Captain Cook Monument. Sea Paradise supplies gear, flotation aids, reef-safe sunscreen, snacks, and drinks. Expect a small-boat feel, cultural stories, and possible dolphins, whales, or flying fish, though wildlife and fish sightings vary.

“Amazing experience, knowledgeable staff and an overall great time! I really loved this it was the perfect amount of time to enjoy a day on the boat and some snorkeling. The staff was friendly and attentive. I am so happy with this experience I would use them again!”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Snorkeling at Kealakekua Bay and the Captain Cook Monument
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

12.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

You’ll sail from Kailua-Kona to Kealakekua Bay aboard a 50-foot catamaran, with Kona coffee and pastries on the way out, about an hour of guided snorkeling, and a deli lunch on the return. The crew shares Hawaiian history, watches for dolphins and seasonal whales, and helps you use the wide water-entry staircase safely.

“We had a wonderful time sailing and snorkeling on this trip.the captain and crew were very personable and attentive. Loved the historical information the captain gave us. I also thought our catamaran seemed a much better vessel than the others moored at Captain Cook bay. I would highly recommend this particular trip!”

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Luxury Catamaran Cruise from Oahu - Afternoon sailing for views and a casual drink
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Luxury Catamaran Cruise from Oahu

13.Luxury Catamaran Cruise from Oahu

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

Sail from Kewalo Basin on the Makani Catamaran for about two hours along Oahu’s coast. Choose an afternoon or sunset departure, watch for dolphins, turtles, and seasonal humpback whales, and enjoy Waikiki and Diamond Head from offshore. Sunset trips include an island-style buffet and one complimentary beverage. Hotel pickup is available for a fee.

“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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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea - Meeting the boat behind the Duke Kahanamoku Statue
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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

14.Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea

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

Spend 2.5 hours aboard Hāwea, a new 50-foot catamaran, snorkeling at Turtle Canyon and sailing past Waikiki. The crew provides masks, fins, snorkels, and flotation belts, then helps you spot turtles and reef fish. Morning trips include ARVO cold brew and Anahola Granola bars. English-speaking crew members such as Julia, Lucy, and Claire have earned warm praise for their calm, helpful approach.

“What a great day! Saw lots of sea life. Great snorkel spot. Seeing the sea turtles were amazing and even saw a few pods of dolphins! Great crew on the catamaran! Amazing time! Totally worth it.”

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Waikiki Deluxe Catamaran Whale Watch - What happens at Kewalo Basin
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Waikiki Deluxe Catamaran Whale Watch

15.Waikiki Deluxe Catamaran Whale Watch

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

Board Hawaii Nautical’s catamaran at Kewalo Basin for about two hours of whale watching off Waikiki. Your captain and crew explain humpback migration while you watch for breaches, tail slaps, and spouts. Drinks, snacks, restrooms, shaded seating, and a re-ride guarantee are included. Shuttle pickup requires selecting the transportation option when booking.

“Great time! Captain Chris and crew were fantastic. Saw some whales, had a great boat ride. Highly recommend this adventure!”

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New in Sailing

★ 4.7Kona Tradewind Catamaran Sail with CocktailsFrom $895 reviews
★ 4.8Kaanapali: Sunset Dinner Catamaran Cruise With DrinksFrom $15355 reviews
★ 4.8Honolulu: 90 Minute Catamaran Sunset SailFrom $5664 reviews
★ 5.0Private Catamaran Sunset Cruise & Optional Snorkeling7 reviews
★ 5.0Snorkel & Sailing Adventure along Ko Olina CoastFrom $1085 reviews
★ 4.7From Maalaea: Whale Watching Catamaran Cruise with DrinksFrom $6926 reviews
★ 4.8Maalaea: West Maui Snorkeling & Sailing Day Trip with LunchFrom $200210 reviews
★ 5.0Kona: Catamaran Sunset Sail with Cocktails and SnacksFrom $1098 reviews
★ 4.9Morning Snorkel Sail to Captain Cook’s MonumentFrom $17849 reviews
★ 3.0BYOB Weekend Sightseeing Sail towards Diamond HeadFrom $234 reviews
★ 4.8Board from Waikiki Beach: Friday Night Fireworks sailFrom $7170 reviews
★ 4.4Board from Waikiki Beach for our Aloha Hour SailFrom $5215 reviews
★ 4.9Board from Waikiki Beach: Scenic Sunset Sail on the HāweaFrom $68217 reviews
★ 4.8Kailua-Kona: Captain Cook Reef Catamaran Day Trip with LunchFrom $80189 reviews
★ 4.8Waikoloa Catamaran Snorkel & Sail Adventure with LunchFrom $18939 reviews

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