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Top 10 Best Hawaii Sailing Trips

Found 105 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 128 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $152.55
 
Sunset Sail Experience at Kona from Honokohau

Sunset Sail Experience at Kona from Honokohau

  • Hawaii
  • Superb128 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $152.55
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 125 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

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Hawaii
  • Superb125 reviews4.8

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

    Free Cancellation
    Start From $110.00
 
 

Sail and Turtle Snorkeling Tour in Waikiki

(4.9 of 204 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

Sail and Turtle Snorkeling Tour in Waikiki

  • Hawaii
  • Superb204 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
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 82 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

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb82 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
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 626 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb626 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.6 of 126 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Start From $139.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • Hawaii
  • Superb126 reviews4.6

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Start From $139.00
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.9 of 12 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb12 reviews4.9

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Sunset Cruise & Whale Watching from Oahu

(3.4 of 10 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

  • Hawaii
  • Good10 reviews3.4

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

    Free Cancellation
    Start From $61.19
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 225 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 Likely to Sell Out

9am Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb225 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
 
 

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

  • Hawaii
  • 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
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.8 of 59 reviews)

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Free Cancellation
Private Tour
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb59 reviews4.8

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

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

(4.8 of 80 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
Private Tour
Start From $34.99
 
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

  • Hawaii
  • Superb80 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $34.99
 
 

Kealakekua Snorkel and Sail Adventure

(5 of 597 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast.  Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets.  Snorkel calm waters and lush coral garde... More

Free Cancellation
Private Tour
Start From $177.65
 
Kealakekua Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Snorkel and Sail Adventure

  • Hawaii
  • Superb597 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast.  Scan the....

    Free Cancellation
    Private Tour
    Start From $177.65
 
 

Oahu Honolulu Fireworks Cruise Boat Tour - NEW YEARS EVE SPECIAL

(4.4 of 23 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Private Tour
Start From $62.80
 
Oahu Honolulu Fireworks Cruise Boat Tour - NEW YEARS EVE SPECIAL Likely to Sell Out

Oahu Honolulu Fireworks Cruise Boat Tour - NEW YEARS EVE SPECIAL

  • Hawaii
  • Exellent23 reviews4.4

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Private Tour
    Start From $62.80
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 43 reviews)

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Private Tour
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • Hawaii
  • Superb43 reviews4.7

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Private Tour
    Start From $119.00
 
 

Day's End Cocktail Sunset Sail

(4.5 of 10 reviews)

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More

Free Cancellation
Private Tour
Start From $169.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Exellent10 reviews4.5

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 210 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb210 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Pau Hana Sunset Cocktail Cruise

(4.9 of 47 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Private Tour
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise Likely to Sell Out

Pau Hana Sunset Cocktail Cruise

  • Hawaii
  • Superb47 reviews4.9

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 83 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
Private Tour
Start From $121.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb83 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $121.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 66 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
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb66 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
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