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Top Oahu Sailing Trips

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15 Oahu Sailing Trips

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Waikiki Sunset Cocktail Sail with Open BarSailing Trips

Waikiki Sunset Cocktail Sail with Open Bar

star-4.5
This lively sunset cruise is great for groups as well as solo travelers. In fact, you’re likely to make fast friends with other passengers over conversation and cocktails including wine, champagne, and a variety of domestic and premium local beers from Maui Brewing. Have a signature cocktail, the “Holokai Hooch,” as you savor the sunset over Oahu.
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Booked by 772 travellers
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$65.39 
From  
US$65.39 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Friday Night Catamaran Fireworks Sail with Open BarSailing Trips

LIKELY TO SELL OUT

Friday Night Catamaran Fireworks Sail with Open Bar

star-4.5
Every Friday night, catch the weekly Hilton Hawaiian Village fireworks display from the water on this evening cruise off Waikiki Beach. The cruise includes an open bar, making this a fun and affordable way to kick off the weekend. This is a great option for families, groups, and celebrations like birthdays and bachelorette parties.
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Booked by 114 travellers
  • 1 hour
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$54.49 
From  
US$54.49 
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  • 1 hour
  • Reserve Now & Pay Later
  • Free Cancellation

3pm Tradewind SailSailing Trips

3pm Tradewind Sail

star-4.5
Discover the beauty of Oahu from the perspective of the water during an afternoon sail. Keep an eye out for a variety of marine life such as dolphins and whales. See local landmarks including the Diamond Head Lighthouse during the sail. Catch a glimpse of Koko Head and Koko Crater, and if the conditions are right, see all the way to Molokai, Maui, and Lanai.
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Booked by 183 travellers
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$43.59 
From  
US$43.59 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

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Polynesian Canoe Sunset SailSailing Trips

Polynesian Canoe Sunset Sail

star-5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and history of place (Mo‘olelo) reflected through the land (ʻāina) and ocean (moana) aboard a classroom on the sea. Our cultural practitioner and crew involve guests in hands on activities, using native materials to make food, clothing, tools, and other traditional items. Ask questions, explore the deck, nets and hulls, take part in poi (taro) pounding or just relax and enjoy. 'Ukulele music and traditional chants ('oli) with locally-sourced traditional food and drinks are all part of this unique experience.
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Booked by 14 travellers
Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$192.00 
From  
US$192.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

12pm Turtle Canyon Snorkel AdventureSailing Trips

LIKELY TO SELL OUT

12pm Turtle Canyon Snorkel Adventure

star-4.5
This combination snorkeling and sailing adventure is perfect for families and nature enthusiasts. Swim with green sea turtles, tropical fish, and other marine life in Turtle Bay near Honolulu. Next, enjoy a cruise around Diamond Head in search of spinner dolphins, and in the winter months, humpback whales. Have some complimentary drinks and snacks as you savor the natural beauty that surrounds you.
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Booked by 495 travellers
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$87.18 
From  
US$87.18 
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

9am Turtle Canyon Snorkel Adventure Sailing Trips

LIKELY TO SELL OUT

9am Turtle Canyon Snorkel Adventure

star-5
Get adventurous during a trip to Honolulu with a morning snorkeling excursion to see green sea turtles. Go under water at Turtle Canyon and swim with a variety of tropical fish, octopus, and turtles. After snorkeling, set sail around Diamond Head to look for Hawaiian spinner dolphins (and humpback whales during the winter months). All snorkel equipment is included.
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Booked by 292 travellers
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$87.18 
From  
US$87.18 
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Polynesian Canoe Day SailSailing Trips

SPECIAL OFFER

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and history of place (Mo‘olelo) reflected through the land (ʻāina) and ocean (moana) aboard a classroom on the sea. Our cultural practitioner and crew involve guests in hands on activities, using native materials to make food, clothing, tools, and other traditional items. Ask questions, explore the deck, nets and hulls, take part in poi (taro) pounding or just relax and enjoy. 'Ukulele music and traditional chants ('oli) with locally-sourced traditional food and drinks are all part of this unique experience. *Note: Saturday & Sunday Daytime Sails are 3 hours instead of 2 and include full meal service.*
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Booked by 10 travellers
Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$119.47 
US$149.34
US$29.87 savings
From  
US$119.47 
US$149.34
US$29.87 savings
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Polynesian Canoe Morning SailSailing Trips

SPECIAL OFFER

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and become immersed in the stories and history of place (Mo‘olelo) reflected through the land (ʻāina) and ocean (moana) aboard a classroom on the sea. Our cultural practitioner and crew involve guests in hands on activities, using native materials to make food, clothing, tools, and other traditional items. Ask questions, explore the deck, nets and hulls, take part in poi (taro) pounding or just relax and enjoy. 'Ukulele music and traditional chants ('oli) with locally-sourced traditional food and drinks are all part of this unique experience. *Morning sails are the best time to see ocean wildlife in Waikiki waters. * *Note: Saturday & Sunday Morning Sails are 3 hours instead of 2*
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Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$119.47 
US$149.34
US$29.87 savings
From  
US$119.47 
US$149.34
US$29.87 savings
Learn More
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Sail Oahu, Hawaii's Premier Luxury Sailing ExperienceSailing Trips

Sail Oahu, Hawaii's Premier Luxury Sailing Experience

Enjoy personalized attention from the captain and crew on this private yacht charter from Oahu. You and your private group will have the run of the boat; you can relax and watch the scenery while sipping drinks from the open bar and enjoying the provided food. Make some stops to explore the underwater world, slipping on the provided snorkel gear to check out the marine flora and fauna.
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Private experience
  • 2 to 4 hours
From  
US$1,760.00 
per group
From  
US$1,760.00 
per group
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  • 2 to 4 hours

Kepoikai Catamaran CharterSailing Trips

LIKELY TO SELL OUT

Kepoikai Catamaran Charter

star-5
Cruise the waters off Waikiki on this private catamaran. During this 1-hour activity, invite up to 37 of your friends and family on board for a journey down the coast of Waikiki and around to Diamond Head. Bring your cameras for fantastic photo ops. Relax on board with your party for special occasions such as weddings, family reunions or birthdays. Multiple departure times offered throughout the day make this a flexible activity that's easy to fit into your schedule while on Oahu.
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Private experience
  • 1 hour
From  
US$1,127.40 
per group
From  
US$1,127.40 
per group
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  • 1 hour

Waikiki Panorama SailDay Cruises

Waikiki Panorama Sail

star-1
Set sail for beautiful Waikiki, the beachfront neighborhood of Honolulu, on this guided, 90-minute tour along the south shore of the island of Oahu in Hawaii. Beginning from the Kewalo Harbor waterfront, head down to Ala Moana Beach Park to Waikiki and the volcanic tuff cone Diamond Head. Along the way, look for Hawaii’s famous green sea turtles and other marine wildlife. Snacks, two free bar beverages and unlimited non-alcoholic drinks are provided. Local hotel pickup and drop-off included.
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Booked by 44 travellers
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$75.01 
From  
US$75.01 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Private Boutique Sailing CharterSailing Trips

Private Boutique Sailing Charter

Your time with us will be your best memory of the islands, with only you and up to 5 other friends! Our friendly crew will take you on an unforgettable ocean sailing experience, off the magnificent North Shore of Oahu. You'll see the sights, feel the wind, taste the spray of the water, as you leave the hustle and bustle of the shore behind. Our 40' Trimaran is safe, comfortable and fast. Winter months we'll go whale watching, hopefully, the dolphins will playfully hang out on our bow, We should see green sea turtles move gracefully on the surface, while abundant, color sea life swim under them. Summer months we'll head to the calm waters of Iconic Waimea Bay where you'll get in the water to snorkel with the turtles and tropical reef fish. We can end our day watching the sun kiss the ocean, as she dips under the waters for one of the most beautiful sunsets anywhere! Whenever the time of the year you join us it'll be the most enjoyable!
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$1,538.47 
per group
From  
US$1,538.47 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Half Day Oahu Combo Adventure: Bike, Sail and SnorkelSailing Trips

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

star-4.5
On this exciting Oahu combo tour, start the day with a downhill bike ride with epic views of the coastline, before boarding a comfortable catamaran for a two-hour snorkeling adventure.  On this Oahu biking and sailing tour, all the necessary equipment is provided along with professional guides, as is round trip transportation and a deli-style lunch.
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Booked by 583 travellers
  • 5 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$138.67 
From  
US$138.67 
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  • 5 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

BYOB Friday Night Fireworks Cruise!Sailing Trips

BYOB Friday Night Fireworks Cruise!

star-1
Friday Night Fireworks in Waikiki Beach is a major tourist draw each week. Avoid the crowds than congregate on the beach and surrounding streets by enjoying the spectacle from a boat as you cruise along the coast of Waikiki. You'll enjoy unobstructed views of the fireworks from the water and plenty of space to move around. The company provides light snacks and refreshments and you can bring your own beverages.
...  More
Booked by 25 travellers
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$75.00 
From  
US$75.00 
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Sailing ExcursionSailing Trips

Sailing Excursion

Experience the thrill of sailing on a performance, racing style trimaran. Relax and enjoy the ride or get hands-on controlling the sails and driving the boat. The power generated from the sails is surprising. Cruise past Diamond Head crater and enjoy the backdrop of the lush Hawaiian Mountains and the Honolulu skyline. We often come across dolphins, flying fish, sea turtles year-round and whales from December to March.
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Small group
  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$149.00 
From  
US$149.00 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation


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