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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

“Definitely recommend booking with them! The 100% guarantee turtle sighting is true! One of the crew members gave us a tour and another was with us in the water as our lifeguard. Great experience all around!”

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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

“I live on windward side of O'ahu and had very little expectations of this cruise. But they really outdid themselves!!! Captain Greg and Shannon were engaging, knowledgeable. We saw a pod of seven whales right by our boat and followed them around until sunset. Perfect weather, great Playlist and awesome spread of snacks. Highly recommend!!!”

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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

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

8.Oahu: Waikiki Sunset Catamaran Sail and Swim

Waikiki sunset catamaran with a refreshing ocean swim, Diamond Head views, and a fun, safety-first crew from Pink Sails Waikiki.

4.6

“This was honestly one of the best experiences I’ve ever had, and for the price it’s a no-brained. Our crew of Jamie, Peter, and Ben made this sail unforgettable for my group! And they went above and beyond: when my sunglasses fell into the ocean, both Peter and Ben were quick to get their goggles…”

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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

“I booked this experience mainly because my mom has always wanted to see and swim with dolphins in the wild. We were all a little nervous prior to boarding the boat just knowing we were going to be swimming in the open water, but all of the staff made us feel so comfortable and confident…”

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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 happened upon a pod of dolphins which followed us for a long while. The crew was very friendly and helpful.”

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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

“Great boat, great captain and crew, great time. The small group tour is the way to go, only six people on a 46 foot catamaran, feels just like a private charter. The cruise is fun and the views are beautiful, but the snorkeling was great. We saw flying fish, turtles, and more. And the food…”

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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.