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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

“Captain Crash and the crew were great all were friendly and knowledgeable. The girls were excellent and guiding us to locations were we could see turtles. We were able to see many different turtles on our trip. We also saw lots of different kinds of fish, a whale, and a pod of dolphins! One of…”

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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

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

“I am not sure luxury would be in my description, Casual would be a better fit. The crew was friendly, but the 2 free drinks is a little misleading. All alcoholic beverages come with a price. It was also a bit crowded with little seating for the 3 hours we were out there.”

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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

“They should know that it's a great excursion, but you may not see the whales which we did not see any, and other people that went on that excursion, they did see whales on this cruise ship with us.They went with a different company.”

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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

“The crew was very helpful and friendly from start to finish, making sure everyone had what they needed to have a good time. The catamaran was also well kept and clean. Plenty of room for people to spread out and enjoy the sail to the snorkeling spot and the time int he water. Was a…”

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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

“It was a cool way to see the fireworks. The crew was very friendly and helpful. The advertisement for this tour mentioned cash bar and complimentary snacks. There weren't any snacks. Not a big deal, but if advertised, should be offered.”

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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

“Terrible, a New Year’s Eve disaster. Viator e-mail told me pick up was 7:30am….it was 5:30am. They moved us to a later tour, but failed to mention it was dolphin watching…NOT swimming with dolphins like the original tour I paid $1000 for.”

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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

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

11.BYOB Waikiki Sunset Swim and Diamond Head Sailing

BYOB Waikiki sunset sail on the Hokulani trimaran with swim and snorkel, plus Diamond Head views, music, and great photo moments.

5.0

“We had a fabulous cruise with the 3 Jacks. Great to be able to BYOB. The music was awesome. The crew gave us a little extra time so we could enjoy the whole sunset. Highly recommend!”

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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

13.Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

90-minute Aloha Hour catamaran sail from Waikiki. Drinks included, Diamond Head views, and possible whale and dolphin sightings.

5.0

“Jenna, Claire & Julia were a fabulous crew!! We got the unexpected surprise of seeing a pod of dolphins showing off for quite some time. We were headed back to shore when we saw it & Jenna turned us back around so we could watch them. It was magnificent!”

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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

“Cancelled the trip with less than 2 hr notice. Why send a review when we didn’t even go on it. Did get a refund”

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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

“We weren’t just dropped off the boat for snorkeling. We had a tour of the reef and when I couldn’t keep up the tour guide towed me. Wonderful fish and a turtle too.”

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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.