SAILING WORLDWIDE
The best days on the water.
The 15 most popular oahu sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
Sail on Moana Catamaran for a Waikiki sunset, with premium cocktails, chances to spot dolphins and humpback whales, and views of Diamond Head.
Most Popular“Great tour! All woman crew... smooth sailing. Drinks were flowing. Remake of the titanic was comedy and the sunset was one to remember.”
Snorkel Turtle Canyon from Waikiki on a catamaran with lunch and guaranteed turtle sightings, plus a free second cruise if none appear.
“The catamaran sail was very enjoyable but the snorkeling was very crowded. Lunch was simply a deli wrap.”
Snorkel Turtle Canyon on a Hawea catamaran from Waikiki. Spot green sea turtles, octopus, and fish, plus gear, snacks, and a sail.
“Saw so many turtles and even dolphins! Crew and guides were lovely. Boat is very modern and clean. The whole trip was beautiful, fun and uplifting!”
2-hr Oahu catamaran snorkel at Turtle Canyon. Turtle sightings are 100% guaranteed. Gear, snacks, and a comfy ride included.
“Great tour for the price! You got to get out on the water for a couple of hours and see Lots of turtles. The had free snacks and drinks available as well. The snorkel was also a guided tour as the 2 girls that snorkeled with us to show us the turtles were very knowledgeable”
Snorkel Turtle Canyon from a Waikīkī catamaran for turtles and fish, with lifeguards and drinks on the sail back. Family-friendly.
“The crew was really accommodating and the boat spacious with a small number of guests. We were able to see turtles and fish and lucked out and saw a monk seal. Also had several dolphins ride the boats bow wake for several minutes. Spectacular!”
Sail off Waikiki on a 40-foot catamaran for a 2-hour sunset cruise with Diamond Head views, complimentary pupus, and BYOB.
“My husband and I went on this sail to celebrate our anniversary, and it turned out to be such a memorable experience. We were a little nervous at first because it was raining and overcast, but the crew reassured us it would clear up—and it did! We’re so glad we didn’t cancel. Krash made the…”
Enjoy a 2-hour luxury catamaran cruise from Oahu with possible dolphins, turtles, and seasonal whales plus Waikiki views and sunset buffet on select sails.
“Wonderful relaxing cruise with skyline views of Waikiki”
Sail from Ko Olina on a 53-foot catamaran, snorkel colorful reefs, and enjoy lunch plus cocktails, with dolphin and whale chances.
“The staff was friendly. The boat was clean. We saw lots of fish when we snorkeled. The sandwiches were tasty. The music playlist was great!”
Watch Waikiki Friday night fireworks from a catamaran with Diamond Head views, music, and a cash bar in about 1h45.
“Super fun, the crew is awesome and entertaining . Beautiful views . Drinks are priced fair . Wish it would set sail a smidge earlier than 630”
Sunset cocktail sail on Waikiki’s Holokai Catamaran with open bar, signature Holokai Hooch, and a social crew on Oahu.
“i can get windy so don’t stress about doing your hair. but it was so beautiful to see the city from the ocean. the staff is very friendly and informative. would definitely do this tour again.”
Parasail over Waikiki with Diamond Head views, capped groups of 12, and multiple height options. Equipment and safety included.
“The overall experience was fun.. I enjoyed it with my husband. The water was beautiful. I felt safe and secure.”
Ke Kai’s Waikiki sunset catamaran sails from the beach with drinks included, Diamond Head views, and a lively crew for ~90 minutes.
“It was a fun trip! The staff was friendly and fun and the views were spectacular. Would definitely do again”
A 90-minute Waikiki sunset catamaran cruise with an included premium bar, light bites, and top-notch Diamond Head views.
“Superb crew! Wonderful time. You won't be disappointed.”
West Oahu catamaran hunt for dolphins, turtles, and seasonal whales with snorkeling, breakfast, and deli lunch, plus hotel pickup options.
“We saw tons of dolphins, some that actually were riding in the front of the boat. One was a mama with her baby. The crew was incredible! Nick, Caden and Ian. The turkey wraps for lunch were fresh and quite tasty! Breakfast consisted of grapes, strawberries, a slice of pineapple and a wonderful biscuit slathered…”
A 90-minute sunset catamaran sail from Waikiki with drinks included, easy ocean access, Diamond Head views, and a relaxed crew vibe.
“You’ll have to take off your shoes and step outside n the water to board. The crew gives you lots of assistance. Wonderful beautiful trip and chance to take great pictures of Diamondhead.”
The sailing ports worth the trip, grouped by the sea they sit on.
