Hawaii Sailing Trips

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Hawaii Activities

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  • Turtle Canyon Snorkel * Turtles guaranteed!!!

    Turtle Canyon Snorkel * Turtles guaranteed!!!

    1,168

    **Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $80.71
    Details
    from
    $80.71
  • Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

    Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

    903

    Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $84.49
    Details
    from
    $84.49
  • Sunset Boat Cruise: Swim and Cruise Waikiki
    Likely to Sell Out

    Sunset Boat Cruise: Swim and Cruise Waikiki

    502

    There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $50.71
    Details
    from
    $50.71
  • Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

    Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

    2,072

    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...
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     2 to 3 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $159
    Details
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    $159
  • Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
    Likely to Sell Out

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

    2,114

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $89.99
    Details
    from
    $89.99
  • Waikiki 3pm Tradewind Sail - Open Bar Included

    Waikiki 3pm Tradewind Sail - Open Bar Included

    241

    Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $53.36
    Details
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    $53.36
  • Waikoloa Signature Catamaran Sunset Sail

    Waikoloa Signature Catamaran Sunset Sail

    381

    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
  • Leila Na Pali Sunset Dinner Sail
    Likely to Sell Out

    Leila Na Pali Sunset Dinner Sail

    488

    Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...
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     5 hours  Free Cancellation
    from
    $263.82
    Details
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    $263.82
  • Waikiki Turtle Snorkel and Sail on Hawea Catamaran

    Waikiki Turtle Snorkel and Sail on Hawea Catamaran

    1,572

    Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $89.56
    Details
    from
    $89.56
  • Afternoon Sail & Snorkel to the Captain Cook Monument

    Afternoon Sail & Snorkel to the Captain Cook Monument

    702

    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
  • Waikiki Sunset Cocktail Sail with Open Bar
    Likely to Sell Out

    Waikiki Sunset Cocktail Sail with Open Bar

    521

    Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $84.77
    Details
    from
    $84.77
  • Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
    Likely to Sell Out

    Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

    675

    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
  • Deluxe Na Pali Sunset Tour on the Lucky Lady

    Deluxe Na Pali Sunset Tour on the Lucky Lady

    1,402

    Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...
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     5 hours  Free Cancellation
    from
    $222.86
    Details
    from
    $222.86
  • Oahu Catamaran Snorkel Tour with Guaranteed Turtles

    Oahu Catamaran Snorkel Tour with Guaranteed Turtles

    1,251

    Experience one Cool Hawaii 's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour offers unbeatable value and family-friendly fun from...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $49.95
    Details
    from
    $49.95
  • 12pm Turtle Canyon Snorkel Adventure

    12pm Turtle Canyon Snorkel Adventure

    296

    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...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $72.05
    Details
    from
    $72.05
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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 Hawaii Sailing Trips?

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

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

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

View all kid-friendly Activities →

Q: Which Hawaii Sailing Trips have Instant Confirmation?

A: Hawaii Sailing Trips with Instant Confirmation include:

View all Activities with Instant Confirmation →

Q: Which Hawaii Sailing Trips have Free Cancellation?

A: 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: I need a ride! Which Hawaii Sailing Trips include Hotel Pickup?

A: No problem. These Hawaii Sailing Trips include Hotel Pickup:

View all Activities with Hotel Pickup →

Q: Got any more Hawaii trip ideas?

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

View all Hawaii Trip Ideas →

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

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

View all tour styles in Hawaii →

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Lowest Price Guarantee

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We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity starts.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
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  • If you find a lower retail or prepaid rate for the same activity, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Hawaii and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased activity into one or more parts sold separately.
  • Cool Hawaii reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Hawaii.

Sorting, ranking, and search results

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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