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15 Best Sailing Tours On Oahu

Oahu’s best days out.

The 15 most popular sailing tours, with prices, run times and the boat or operator behind each one. The trips worth a morning on the water or a day around the island, and what each one actually gets you.

15 Best Sailing Tours On Oahu

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed - Getting in the water: safety briefings and gear that actually helps
Catamaran Sailing Cruises, Cruises & Boat Tours, Lunch Experiences, Oahu, Sailing, Snorkeling Tours, Tour Reviews

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed - The catamaran ride: comfortable, not crowded
Catamaran Sailing Cruises, Cruises & Boat Tours, Oahu, Sailing, Snorkeling Tours, Tour Reviews, Tours

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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

Oahu catamaran snorkel at Turtle Canyon Reef with a 100% turtle sighting guarantee, guided swim, and onboard snacks.

5.0

“Got to see lots of fish and turtles. Also got to see a cute seal on the way back. There were a few snacks on the way back which was nice as we were hungry. Only downside is we didn’t get to see the dog on this trip”

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Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB - Stop one: the Diamond Head sea-level moment
Catamaran Sailing Cruises, Cruises & Boat Tours, Evening Experiences, Food, Food & Drink, Oahu, Sailing, Tour Reviews

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

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

Trade Waikiki crowds for a 2-hour sunset catamaran from Ala Moana with Diamond Head views, complimentary pupus, and BYOB.

5.0

“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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Luxury Catamaran Cruise from Oahu - Ala Moana Beach Park and Waikiki from the water
Catamaran Sailing Cruises, Cruises & Boat Tours, Oahu, Sailing, Tour Reviews, VIP

Luxury Catamaran Cruise from Oahu

4.Luxury Catamaran Cruise from Oahu

Fast Oahu luxury catamaran with Waikiki views, dolphin and turtle spotting, and seasonal whales. Sunset includes buffet and a drink.

4.5

“We were very disappointed in this excursion all we did was ride to Diamondhead turn around and ride back no near ration no talking a little bit of music and that was it was not worth the money”

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Waikiki Deluxe Catamaran Whale Watch - The Catamaran Experience: Seating, Stability, and Comfort
Catamaran Sailing Cruises, Cruises & Boat Tours, Oahu, Sailing, Tour Reviews, Whale & Dolphin Watching, Whale Watching

Waikiki Deluxe Catamaran Whale Watch

5.Waikiki Deluxe Catamaran Whale Watch

Waikiki deluxe catamaran whale watch from Kewalo Basin with a premium bar, humpback migration talk, and re-ride if no whales.

4.5

“The boat and the crew were awesome. Booking via Viator was a poor experience as they provided no information on boat name, nor dock/slip number. Had to run around for 15 min to find the actual boat. Please consider updating boat information so customers can enjoy the full experience.”

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Ko Olina Catamaran Sail and Snorkel with Lunch - Boarding the 53-foot catamaran: space, shade, and a crew that works
Catamaran Sailing Cruises, Cruises & Boat Tours, Lunch Experiences, Oahu, Sailing, Snorkeling Tours, Tour Reviews

Ko Olina Catamaran Sail and Snorkel with Lunch

6.Ko Olina Catamaran Sail and Snorkel with Lunch

Sail and snorkel off Ko Olina on a 53-foot catamaran with lunch, snorkel gear, and included drinks for adults 21+.

5.0

“This excursion was by far the best experience we had. For the price it is so worth it. They gave us three free drinks, an amazing sandwich for lunch, and let us snorkel and jump off the boat. We saw wildlife and lots of fish. You won’t regret booking!”

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Waikiki: Friday Night Fireworks Catamaran Cruise - Diamond Head Views While the Coastline Forms a Night Backdrop
Catamaran Sailing Cruises, Cruises & Boat Tours, Evening Experiences, Oahu, Sailing, Tour Reviews

Waikiki: Friday Night Fireworks Catamaran Cruise

7.Waikiki: Friday Night Fireworks Catamaran Cruise

Waikiki Friday night fireworks from a catamaran: Diamond Head views, sunset sailing, music, and a cash bar on a 1h45 cruise.

4.5

“Good experience. The crew was friendly and the boat ride was fun but keep in mind you sit on the boat for over an hour and watch a maybe 10 minutes firework show. They sell drinks but would be nice if they carry some snacks but understand they don’t want more waste on board. Would…”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - The 2-Hour Plan: From Dock to Diamond Head to Waterline Night
Catamaran Sailing Cruises, Cruises & Boat Tours, Evening Experiences, Honolulu, Sailing, Sunset & Dinner Cruises, Tour Reviews

Oahu: Waikiki Sunset Catamaran Sail and Swim

Swim with Dolphins Catamaran with Waterslide & Lunch on Oahu - Getting Ready to Swim With Dolphins (This Part Is No Joke)
Catamaran Sailing Cruises, Cruises & Boat Tours, Dolphin Watching, Lunch Experiences, Oahu, Sailing, Tour Reviews, Whale & Dolphin Watching

Swim with Dolphins Catamaran with Waterslide & Lunch on Oahu

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

Swim with wild dolphins off Oahu, then snorkel at Makaha with a 21-ft waterslide, lunch, and ocean toys included.

4.5

“Mahalo Mahalo Mahalo to Team Poseidon! The most amazing 4 hrs at Oahu's western coastline. We were able to see a pod of spinner dolphins within 5mins of cruising. After a while, we were informed of spotting pilot whales by the direction we are heading to, we had the 1st/2nd jump off the ocean and…”

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Private Catamaran Cruise and Snorkeling Tour in Honolulu - Getting on board: meeting point, timing, and group size
Catamaran Sailing Cruises, Cruises & Boat Tours, Oahu, Private, Sailing, Snorkeling, Snorkeling Tours, Tour Reviews, Tours

Private Catamaran Cruise and Snorkeling Tour in Honolulu

10.Private Catamaran Cruise and Snorkeling Tour in Honolulu

Private 2-hour catamaran cruise off Honolulu with snorkeling, turtle sightings, Diamond Head views, and BYOB comfort for up to six.

5.0

“Spectacular crew!!! Wonderful snorkel spots and experience in the ocean. We held a sea urchin, sea cucumber, and an octopus as well seeing a plethora of fish and turtles. We topped it off, watching a pod of dolphins play around the boat. Amazing!”

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BYOB Waikiki Sunset Swim and Diamond Head Sailing - The 2-Hour Waikiki Sunset Swim Flow (And Where the Best Moments Usually Land)
Cruises & Boat Tours, Diamond Head Tours, Evening Experiences, Oahu, Sailing, Tour Reviews

BYOB Waikiki Sunset Swim and Diamond Head Sailing

Small Group Yacht Sunset Cruise from Oahu - Check-in at Ko Olina Marina and what to expect when you arrive
Cruises & Boat Tours, Evening Experiences, Oahu, Sailing, Sunset & Dinner Cruises, Tour Reviews

Small Group Yacht Sunset Cruise from Oahu

12.Small Group Yacht Sunset Cruise from Oahu

Small-group Ko Olina sunset yacht cruise with chef tasting menu, hosted bar, and wildlife spotting. Up to 6 guests, 2.5 hours.

5.0

“Captain Travis and Taylor made this experience amazin!. Drinks were amazing, food was amazing, the whole evening was wonderful. 10000% recommend this charter and will definitely be back and do it all again!”

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Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran - The Aloha Hour schedule: what that 90 minutes really delivers
Catamaran Sailing Cruises, Cruises & Boat Tours, Oahu, Sailing, Tour Reviews

Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

2-Hour Oahu Sunset Catamaran Sail - Boarding at Waipahe Pl: Check-In, Waivers, and Group Size Reality
2-Hour Experiences, Catamaran Sailing Cruises, Cruises & Boat Tours, Evening Experiences, Oahu, Sailing, Sunset & Dinner Cruises, Tour Reviews

2-Hour Oahu Sunset Catamaran Sail

14.2-Hour Oahu Sunset Catamaran Sail

A 2-hour Ko Olina sunset catamaran with charcuterie, snacks, and complimentary cocktails, cruising off Oahu’s coast for big golden-hour views.

5.0

“We had a wonderful time. The crew was amazing. The boat was clean. The food was great and the service was even better. When we come back to Oahu, we will take the same cruise.”

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Oahu Small Group Snorkel Tour with Yacht Cruise - Hosted bar and lunch: not an afterthought, part of the pacing
Cruises & Boat Tours, Oahu, Sailing, Snorkeling Tours, Tour Reviews, Tours

Oahu Small Group Snorkel Tour with Yacht Cruise

15.Oahu Small Group Snorkel Tour with Yacht Cruise

Oahu small-group yacht snorkel tour from Ko Olina with a hosted bar, lunch, and guided snorkeling with turtles and reef fish.

5.0

“This experience was the highlight of our trip, and it is absolutely worth every penny. The boat was beautiful, and the views we were able to see were stunning. The staff was incredibly kind and patient, and the small group of 6 was the perfect size for a tour like this. We saw tons of…”

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More Sailing Tours On Oahu

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Explore Oahu

From Pearl Harbor to the North Shore, the reef off Waikiki to the valleys of the windward coast. Every way to spend a day on the island.