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Top 10 Best Big Island of Hawaii Sailing Trips

Found 15 Sailing Trips activities in Big Island of Hawaii. Sort by Popularity.
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 382 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Big Island of Hawaii
  • Superb382 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

Kona Catamaran Sunset Sail

(4.8 of 186 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 $128.14
 
Kona Catamaran Sunset Sail

Kona Catamaran Sunset Sail

  • Big Island of Hawaii
  • Superb186 reviews4.8

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

    Free Cancellation
    Start From $128.14
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 519 reviews)

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 adventure will begin in the turquoise waters a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Big Island of Hawaii
  • Superb519 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 703 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 a... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Big Island of Hawaii
  • Superb703 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 464 reviews)

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 adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Big Island of Hawaii
  • Superb464 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 676 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 gardens u... More

Free Cancellation
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Big Island of Hawaii
  • Superb676 reviews5

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

    Free Cancellation
    Start From $189.00
 
 
-16% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

(4.8 of 40 reviews)

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More

Special Offer
Free Cancellation
Start From $99.96
(Saving 16% ) $119.00
 
-16% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

  • Big Island of Hawaii
  • Superb40 reviews4.8

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....

    Special Offer
    Free Cancellation
    Start From $99.96
    (Saving 16% ) $119.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 245 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
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Big Island of Hawaii
  • Superb245 reviews4.9

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

    Free Cancellation
    Start From $136.19
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 813 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $145.41
 
Sunset and Manta Ray Snorkel Adventure

Sunset and Manta Ray Snorkel Adventure

  • Big Island of Hawaii
  • Superb813 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $145.41
 
 

Sunset Cocktail Cruise from Anaeho'omalu Bay

(4.8 of 60 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Start From $165.00
 
Sunset Cocktail Cruise from Anaeho'omalu Bay

Sunset Cocktail Cruise from Anaeho'omalu Bay

  • Big Island of Hawaii
  • Superb60 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Start From $165.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 98 reviews)

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snorkeling cruise. As you head out across the clear Pacific waters, enjoy panoramic views of volcanic mountains, golden coastline, and ... More

Free Cancellation
Start From $169.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Big Island of Hawaii
  • Superb98 reviews4.6

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snork....

    Free Cancellation
    Start From $169.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 733 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

  • Big Island of Hawaii
  • Superb733 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
 
 

Sunset Cruise with the Whales from Anaeho'omalu Bay

(4.8 of 46 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Start From $165.00
 
Sunset Cruise with the Whales from Anaeho'omalu Bay Likely to Sell Out

Sunset Cruise with the Whales from Anaeho'omalu Bay

  • Big Island of Hawaii
  • Superb46 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Start From $165.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • Big Island of Hawaii
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Start From $276.00
 
 

Afternoon Kealakekua Snorkel and Sail

(5 of 11 reviews)

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary of Kealakekua Bay (home of the Captain Cook Monument). Explore the incredible world under the water with its abundance of marine li... More

Free Cancellation
Start From $189.00
 
Afternoon Kealakekua Snorkel and Sail Likely to Sell Out

Afternoon Kealakekua Snorkel and Sail

  • Big Island of Hawaii
  • Superb11 reviews5

Join us for a sensational 3.5 hour coastal sail, which includes snorkeling in the marine sanctuary o....

    Free Cancellation
    Start From $189.00
 
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