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OAHU

14 Best Sailing Tours On Oahu

Oahu’s best days out.

The 14 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.

14 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

“Such a beautiful experience! The staff were so kind. It was worth it for sure! The sunset was gorgeous and we even saw 2 whales! They served beverages and had a nice spread of food as well! 10/10 would 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

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

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

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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

“What a lovely experience! I had been wanting to do a catamaran in Hawaii and finally was able to do it. A friend recommend this to me. Great and helpful staff! Lovely snorkeling!”

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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

“Boat crew was great! Very helpful and gave great information. Boat ride got a little bumpy and the crew was great about giving information to make you feel comfortable. Fireworks show was very underwhelming and disappointing.”

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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

“Read careful No guarantee swim with dolphins if no doubles you can try again at 50% off which is crazy You have to request a glass of water and when they are bust you do without bring water if you go and be aware you may or may not swim with dolphins and/or turtles grandkids…”

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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

“Great communication, we met our two-man crew and were immediately comfortable and having fun on the boat. Blue tooth stereo, pouring our own drinks. Made a stop to see turtles, and another to splash around. Even went out far to look unsuccessfully for whales. Great company, and they even gave us perfect weather.”

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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

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

“What a fun time! Wow! Crew was incredible. Kept us laughing the entire time, not to mention the amazing sail and swim. We saw dolphins and turtles. A rainbow and impeccable sunset. If I could give 10 stars, I would. Perfect ending to our trip.”

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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

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

“Even though we didn’t see any whales or even a sunset (cloudy), the captain and crew were so friendly and helpful. They served the drinks quickly and frequently (open bar - recommend the naked pirate) and we had wonderful conversations with them and other passengers while we enjoyed cruising up the coast of Oahu.”

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