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Top 10 Best Oahu Sailing Trips

Found 61 Sailing Trips activities in Oahu. Sort by Popularity.
 

2-Hour Whale Watching from Oahu

(4.6 of 685 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

Free Cancellation
Start From $50.71
 
2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

  • Oahu
  • Superb685 reviews4.6

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

    Free Cancellation
    Start From $50.71
 
 

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

(4.9 of 1,789 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
  • Superb1,789 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
 
 
-25% Waikiki Catamaran Adventure: Snorkel with Sea Turtles

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 2,010 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

Special Offer
Free Cancellation
Start From $81.46
(Saving 25% ) $108.62
 
-25% Waikiki Catamaran Adventure: Snorkel with Sea Turtles

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • Oahu
  • Superb2,010 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $81.46
    (Saving 25% ) $108.62
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.7 of 1,350 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
  • Superb1,350 reviews4.7

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
 
 
-15% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

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

(4.9 of 172 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

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

  • Oahu
  • Superb172 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
 
 
-10% Sunset Cruise & Whale Watching from Oahu

Sunset Cruise & Whale Watching from Oahu

(4 of 21 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

Special Offer
Free Cancellation
Start From $55.07
(Saving 10% ) $61.19
 
-10% Sunset Cruise & Whale Watching from Oahu

Sunset Cruise & Whale Watching from Oahu

  • Oahu
  • Very Good21 reviews4

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

    Special Offer
    Free Cancellation
    Start From $55.07
    (Saving 10% ) $61.19
 
 

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

(4.9 of 583 reviews)

WE WILL BE IN DRY DOCK THRU 2/15/25. LOOK FOR OUR COMPLETELY NEW AND REIMAGINED VESSEL, THE KAHALA KAI! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985 and ar... 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
  • Superb583 reviews4.9

WE WILL BE IN DRY DOCK THRU 2/15/25. LOOK FOR OUR COMPLETELY NEW AND REIMAGINED VESSEL, THE KAHALA K....

    Free Cancellation
    Start From $54.95
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 425 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

Free Cancellation
Start From $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Oahu
  • Superb425 reviews4.7

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

    Free Cancellation
    Start From $47.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 881 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
  • Superb881 reviews4.7

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

    Free Cancellation
    Start From $84.99
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 442 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
  • Superb442 reviews4.8

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
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 233 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

Special Offer
Free Cancellation
Start From $77.04
(Saving 20% ) $96.30
 
-20% 9am Turtle Canyon Snorkel Adventure Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • Oahu
  • Superb233 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $77.04
    (Saving 20% ) $96.30
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.9 of 215 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 $109.00
 
Sail and Turtle Snorkeling Tour in Waikiki Likely to Sell Out

Sail and Turtle Snorkeling Tour in Waikiki

  • Oahu
  • Superb215 reviews4.9

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

    Free Cancellation
    Start From $109.00
 
 

BYOB Waikiki Sunset Swim and Diamond Head Sailing

(5 of 140 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 Likely to Sell Out

BYOB Waikiki Sunset Swim and Diamond Head Sailing

  • Oahu
  • Superb140 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 94 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 $60.00
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Oahu
  • Superb94 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 $60.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 91 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Oahu
  • Superb91 reviews4.9

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Start From $125.00
 
 

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

(4.9 of 95 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 Likely to Sell Out

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

  • Oahu
  • Superb95 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
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 254 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

Special Offer
Free Cancellation
Start From $77.04
(Saving 20% ) $96.30
 
-20% 12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • Oahu
  • Superb254 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $77.04
    (Saving 20% ) $96.30
 
 

Polynesian Canoe Sunset Sail

(4.9 of 117 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

Free Cancellation
Start From $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Oahu
  • Superb117 reviews4.9

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

    Free Cancellation
    Start From $250.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 130 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 $110.00
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Oahu
  • Superb130 reviews4.8

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

    Free Cancellation
    Start From $110.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 6 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • Oahu
  • Superb6 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
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