Big Island of Hawaii Sailing Trips

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Big Island of Hawaii Activities

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  • Waikoloa Signature Catamaran Sunset Sail

    Waikoloa Signature Catamaran Sunset Sail

    383

    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...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
    from
    $149
    Details
    from
    $149
  • Afternoon Sail & Snorkel to the Captain Cook Monument

    Afternoon Sail & Snorkel to the Captain Cook Monument

    707

    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...
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     3 hours  Free Cancellation
    from
    $136.19
    Details
    from
    $136.19
  • Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

    Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

    678

    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...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    $189
    Details
    from
    $189
  • Snorkel with Manta Rays Guaranteed
    Likely to Sell Out

    Snorkel with Manta Rays Guaranteed

    719

    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...
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     1 hour 30 minutes  Free Cancellation
    from
    $141.57
    Details
    from
    $141.57
  • Kona Catamaran Sunset Sail
    Likely to Sell Out

    Kona Catamaran Sunset Sail

    194

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $149
    Details
    from
    $149
  • Deluxe Sail & Snorkel to the Captain Cook Monument

    Deluxe Sail & Snorkel to the Captain Cook Monument

    521

    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...
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     4 hours 30 minutes  Free Cancellation
    from
    $177.73
    Details
    from
    $177.73
  • Waikoloa Catamaran Snorkel Sail Including Lunch

    Waikoloa Catamaran Snorkel Sail Including Lunch

    96

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $169
    Details
    from
    $169
  • Sunset and Manta Ray Snorkel Adventure
    Likely to Sell Out

    Sunset and Manta Ray Snorkel Adventure

    813

    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...
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     2 hours 15 minutes  Free Cancellation  Instant Confirmation
    from
    $145.41
    Details
    from
    $145.41
  • Kona Tradewind Catamaran Day Sail
    Likely to Sell Out

    Kona Tradewind Catamaran Day Sail

    42

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $119
    Details
    from
    $119
  • Deluxe Sail & Snorkel to the Captain Cook Monument

    Deluxe Sail & Snorkel to the Captain Cook Monument

    464

    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"...
    Read More

     4 hours 30 minutes  Free Cancellation
    from
    $179.27
    Details
    from
    $179.27
  • Afternoon Sail & Snorkel to the Captain Cook Monument

    Afternoon Sail & Snorkel to the Captain Cook Monument

    243

    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...
    Read More

     3 hours  Free Cancellation
    from
    $136.19
    Details
    from
    $136.19
  • Sunset Cocktail Cruise from Anaeho'omalu Bay

    Sunset Cocktail Cruise from Anaeho'omalu Bay

    61

    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....
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $165
    Details
    from
    $165
  • Sunset Cruise with the Whales from Anaeho'omalu Bay

    Sunset Cruise with the Whales from Anaeho'omalu Bay

    42

    Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $165
    Details
    from
    $165
  • Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
    Likely to Sell Out

    Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

    10

    Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast....
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $125
    Details
    from
    $125
  • Afternoon Kealakekua Snorkel and Sail
    Likely to Sell Out

    Afternoon Kealakekua Snorkel and Sail

    11

    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)....
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     3 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $189
    Details
    from
    $189
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Big Island of Hawaii Sailing Trips?

A: According to verified reviews on Cool Hawaii and TripAdvisor, the best Big Island of Hawaii Sailing Trips are:

Q: What are the best kid-friendly options for Big Island of Hawaii Sailing Trips Activities?

A: According to verified reviews on Cool Hawaii and TripAdvisor, the best kid-friendly Big Island of Hawaii Sailing Trips are:

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Q: Which Big Island of Hawaii Sailing Trips have Instant Confirmation?

A: Big Island of Hawaii Sailing Trips with Instant Confirmation include:

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Q: Which Big Island of Hawaii Sailing Trips have Free Cancellation?

A: Big Island of Hawaii Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include:

View all Activities with Free Cancellation →

Q: Got any more Big Island of Hawaii trip ideas?

A: We sure do. Check out our curated lists of hand-picked Big Island of Hawaii Activities.

View all Big Island of Hawaii Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Big Island of Hawaii?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Big Island of Hawaii are:

View all tour styles in Big Island of Hawaii →

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