Hawaii · SAILING

The 15 Best Catamaran & Sailing Trips in Hawaii

41 tours  ·  from $35 a head

A catamaran buys you shade, a swim ladder and a flat deck in a channel that is rarely flat. These 15 compare the Waikiki, Maalaea and Kona boats on group size, lunch and what the trade wind does to each.

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - What the power catamaran adds
Cruises & Boat Tours, Sailing, Sailing in the Big Island, Snorkeling, Snorkeling in the Big Island, Tour Reviews, Tours in the Big Island

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

Join Hang Loose Boat Tours for a four-hour catamaran trip from Kona to historic Kealakekua Bay. Captain Aiden, Captain Bryce, Jordan, and the crew guide you to clear water filled with reef fish and coral, with dolphins or winter humpback whales possible along the way. Gear, lunch, drinks, and a boat slide are included.

“Jordan went far beyond in helping my wife and I He is the best Perk and Judy would say he is the best back hand you have”

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Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Meeting the Moana Catamaran at Kewalo Basin Harbor
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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

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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Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - The water can be calm, choppy, or crowded
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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 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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Waikiki Turtle Snorkel and Sail on Hawea Catamaran - The Hawea catamaran and the ride from Waikiki
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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

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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Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed - What happens at the 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

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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Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - The Two-Hour Route, Step by Step
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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

Board Quicksilver Charters’ double-deck power catamaran at Maalaea Harbor for a two-hour whale watch from December 1 through April 30. Look for breaches, spy-hops, tail slaps, mothers, and calves, while the captain and crew explain whale behavior. Hydrophones let you hear the songs below, and drinks, restrooms, and shaded seating are included.

“The tour was wonderful! We saw so many whales. Worth the $$. Dave was amazing and super attentive. The Captain (forgot his name but an Aussie and fr New Zealand) was very informative and the perfect host. There was a 3rd gentleman on the tour who was at the bar. Also, great!”

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Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure - Getting ready for the water
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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 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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Waikiki Signature Sunset Catamaran Sail - A Sunset Cruise Built Around Diamond Head
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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

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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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB - Sailing toward Diamond Head
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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 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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Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Red Hill snorkeling: know what you are booking
Cruises & Boat Tours, Dolphin Watching, Sailing, Sailing in the Big Island, Snorkeling, Snorkeling in the Big Island, Tour Reviews, Tours in the Big Island, VIP

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

Board Body Glove’s large catamaran from Kailua-Kona for a 4.5-hour outing along the Gold Coast. You’ll get breakfast, lunch, snorkel gear, reef-safe sunscreen, about two hours in the water, and a good chance to spot dolphins or seasonal whales. Captain Erica, Adam, Brianna, and Taylor have all been praised for attentive service, though the Red Hill snorkel site is not Kealakekua Bay.

“There were many snorkeling companies, but I never regret choosing this.The staff were super kind and the breakfast and lunch they provided were so delicious with fresh ingredients. On the way to the snorkeling spot, we could see a group of dolphins. Besides snorkeling, they provided various swimming equipment for children to enjoy. It was a very satisfying experience and I want to do it again!!”

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Afternoon Sail & Snorkel to the Captain Cook Monument - The Captain Cook Monument from the water
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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

Join Sea Paradise at 1:45 pm for a three-hour afternoon sail from Keauhou Bay to Kealakekua Bay. You will receive snorkel gear, flotation aids, reef-safe sunscreen, snacks, and drinks. A crew-led snorkel outing, cultural stories, and possible dolphin sightings round out the trip. Alcohol is available to buy afterward.

“Great snorkel and sail experience! Such a blast and all of the crew was great! I highly recommend this tour.”

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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Sailing south along the Kona coast
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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

Sail Kona’s coast on Kona Style’s 50-foot catamaran to Kealakekua Bay, where you’ll receive snorkel gear, safety instruction, and about an hour in the marine sanctuary near the Captain Cook Monument. Breakfast, Kona coffee, lunch, drinks, flotation noodles, and Hawaiian history are included. The morning starts at 8:30 a.m. in Kailua-Kona.

“About an hour along the coast to the snorkel site, about an hour snorkeling, and then back (with a few stops along the way). Knowledgable and friendly crew. Stunningly clear and beautiful water. Colorful array of fish and sea life…. Great excursion!”

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Luxury Catamaran Cruise from Oahu - Wildlife watching from the rail
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Luxury Catamaran Cruise from Oahu

13.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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Waikiki Beach: Turtle Snorkeling and Sailing on Hāwea - Boarding Hāwea 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 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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Waikiki Deluxe Catamaran Whale Watch - Whale season, sightings, and the no-whale promise
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Waikiki Deluxe Catamaran Whale Watch

15.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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New in Sailing

★ 4.8Kona: Captain Cook Reef Catamaran Day Trip with LunchFrom $80189 reviews
★ 4.8Waikoloa Catamaran Snorkel & Sail Adventure with LunchFrom $18939 reviews
★ 4.8Catamaran Sunset Sail with CocktailsFrom $15968 reviews
★ 5.0Kona Signature Catamaran Sunset SailFrom $109218 reviews
★ 4.9Board from Waikiki Beach: Scenic Sunset Sail on the HāweaFrom $68217 reviews
★ 5.0Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki CoastFrom $34236 reviews
★ 5.0Waikiki 3pm Tradewind Sail – Open Bar IncludedFrom $53246 reviews
★ 5.0Afternoon Sail & Snorkel to the Captain Cook MonumentFrom $136246 reviews
★ 4.8Molokini Snorkel and Performance Sail with LunchFrom $200224 reviews
★ 5.0Board from Waikiki Beach for a scenic Sunset Sail on the HāweaFrom $72277 reviews
★ 4.5West Oahu Dolphin Watch and Snorkel Sail with LunchFrom $125320 reviews
★ 5.0Kalapaki Kai Sunset Catamaran CruiseFrom $109349 reviews
★ 4.7Waikiki Sunset Catamaran Cocktail CruiseFrom $99348 reviews
★ 4.8From Ma’alaea: ‘Alihilani Sunset Sail Catamaran TourFrom $114348 reviews
★ 5.0Waikiki Beach Sunset SailFrom $70378 reviews

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