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Top 10 Best Oahu Sailing Trips

Found 65 Sailing Trips activities in Oahu. Sort by Popularity.
 
-5% 2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

(4.6 of 899 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Special Offer
Free Cancellation
Start From $48.17
(Saving 5% ) $50.71
 
-5% 2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

  • Oahu
  • Superb899 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Special Offer
    Free Cancellation
    Start From $48.17
    (Saving 5% ) $50.71
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 1,891 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $84.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • Oahu
  • Superb1,891 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $84.99
 
 

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 2,052 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $108.62
 
Waikiki Catamaran Adventure: Snorkel with Sea Turtles

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • Oahu
  • Superb2,052 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $108.62
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,427 reviews)

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea turtle cleaning station. Our crew shows you not only turtles but also hidden creatures such as he’e (octopus) and ka hoku kai (st... More

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • Oahu
  • Superb1,427 reviews4.8

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....

    Free Cancellation
    Start From $84.77
 
 

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

(4.9 of 611 reviews)

AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off o... More

Free Cancellation
Start From $54.95
 
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

  • Oahu
  • Superb611 reviews4.9

AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....

    Free Cancellation
    Start From $54.95
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.7 of 470 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Start From $85.00
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • Oahu
  • Superb470 reviews4.7

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $85.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 140 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Oahu
  • Superb140 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 
-10% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 444 reviews)

There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More

Special Offer
Free Cancellation
Start From $42.30
(Saving 10% ) $47.00
 
-10% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Oahu
  • Superb444 reviews4.7

There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....

    Special Offer
    Free Cancellation
    Start From $42.30
    (Saving 10% ) $47.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 901 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Oahu
  • Superb901 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $84.99
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 144 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
BYOB Waikiki Sunset Swim and Diamond Head Sailing

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • Oahu
  • Superb144 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 105 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Oahu
  • Superb105 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 146 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Start From $39.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Oahu
  • Superb146 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Start From $39.99
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 243 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Start From $96.30
 
9am Turtle Canyon Snorkel Adventure

9am Turtle Canyon Snorkel Adventure

  • Oahu
  • Superb243 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Start From $96.30
 
 

Sunset Cruise & Whale Watching from Oahu

(4.5 of 62 reviews)

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden hues of the evening sky, where you'll have the chance to witness majestic whal... More

Free Cancellation
Start From $61.19
 
Sunset Cruise & Whale Watching from Oahu Likely to Sell Out

Sunset Cruise & Whale Watching from Oahu

  • Oahu
  • Exellent62 reviews4.5

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....

    Free Cancellation
    Start From $61.19
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.9 of 235 reviews)

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Free Cancellation
Start From $99.00
 
Sail and Turtle Snorkeling Tour in Waikiki Likely to Sell Out

Sail and Turtle Snorkeling Tour in Waikiki

  • Oahu
  • Superb235 reviews4.9

Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....

    Free Cancellation
    Start From $99.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 118 reviews)

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

Special Offer
Free Cancellation
Start From $225.00
(Saving 10% ) $250.00
 
-10% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Oahu
  • Superb118 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Special Offer
    Free Cancellation
    Start From $225.00
    (Saving 10% ) $250.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.9 of 199 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Special Offer
Free Cancellation
Start From $62.01
(Saving 15% ) $72.96
 
-15% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Oahu
  • Superb199 reviews4.9

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Special Offer
    Free Cancellation
    Start From $62.01
    (Saving 15% ) $72.96
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 89 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Oahu
  • Superb89 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Start From $99.00
 
 

Oahu 3pm Tradewind Sail from Honolulu

(4.8 of 226 reviews)

This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More

Free Cancellation
Start From $59.10
 
Oahu 3pm Tradewind Sail from Honolulu Likely to Sell Out

Oahu 3pm Tradewind Sail from Honolulu

  • Oahu
  • Superb226 reviews4.8

This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....

    Free Cancellation
    Start From $59.10
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 16 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Oahu
  • Superb16 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
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