Sailing Trips in Oahu
Top 10 Best Oahu Sailing Trips
Found 63 Sailing Trips activities in Oahu. Sort by Popularity. - Page 3Polynesian 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 b... More
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Polynesian Canoe Morning Sail
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Oahu
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Superb16 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
(Saving 10% )
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
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Oahu
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Superb32 reviews4.7
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Private Tour

Diamond Head Sunset Sail
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Oahu
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
Waikiki Private Sunset Sail Romantic and Private
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More
Private Tour

Waikiki Private Sunset Sail Romantic and Private
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Oahu
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Superb15 reviews4.7
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More
Private Tour

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
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Oahu
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Superb4 reviews5
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....
Private Tour
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
Private Tour

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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Oahu
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
Private Tour
Luxury Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More
Private Tour

Luxury Diamond Head Sunset Sail
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Oahu
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Superb3 reviews5
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
3 Hour Luxury Private Sailing Catamaran for 7-12 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

3 Hour Luxury Private Sailing Catamaran for 7-12 People
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Oahu
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Superb3 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour

BYOB Friday Night Fireworks Cruise
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Oahu
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Exellent5 reviews4.2
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour
Friday Night Waikiki Fireworks Sail
Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More
Private Tour

Friday Night Waikiki Fireworks Sail
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Oahu
Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....
Private Tour
Private Whale Watching Sailing Adventure
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More
Private Tour

Private Whale Watching Sailing Adventure
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Oahu
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Good2 reviews3.5
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....
Private Tour
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Private Tour

Waikiki Sunset Boat Cruise
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Oahu
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Superb10 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Private Tour
2hr Luxury Private Sailing Catamaran for 7-12 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

2hr Luxury Private Sailing Catamaran for 7-12 People
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Oahu
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Superb10 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private South Shore Sail Charter
Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More
Private Tour

Private South Shore Sail Charter
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Oahu
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Superb2 reviews5
Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....
Private Tour
Moana’s Luxury semi-private Sunset Cruise on Nalu
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More
Private Tour

Moana’s Luxury semi-private Sunset Cruise on Nalu
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Oahu
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Exellent6 reviews4.3
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
Private Tour
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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Oahu
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Exellent6 reviews4.3
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Private Swim and Sail Charter (Kewalo Harbor)
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More
Private Tour

Private Swim and Sail Charter (Kewalo Harbor)
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Oahu
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Exellent6 reviews4.3
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
Private Tour
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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Oahu
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Exellent6 reviews4.3
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private Cruise Swim with Dolphin
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More
Private Tour

Private Cruise Swim with Dolphin
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Oahu
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Exellent6 reviews4.3
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....
Private Tour
Private Morning Ceremony Sailing Charter
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More
Private Tour

Private Morning Ceremony Sailing Charter
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Oahu
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Exellent6 reviews4.3
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....
Private Tour