Hawaii Sailing Trips

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Hawaii Activities

Attractions

Guides

Calendar

Afternoon Sail With the Whales from Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (1)

Afternoon Sail With the Whales from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (1)
from
$100.22
Midmorning Whale Watch from Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.5 (2)

Midmorning Whale Watch from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.5 (2)
from
$100.22
Waikiki Turtle Snorkeling Adventure(8am)
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
5.0 (83)

Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
5.0 (83)
from
$100
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Honolulu, USA
4.7 (2,096)

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

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...

2 to 3 hours • Hotel pickup offered • Free Cancellation
2 to 3 hours • Hotel pickup offered • Free Cancellation
2 to 3 hours • Hotel pickup offered • Free Cancellation
4.7 (2,096)
from
$99
Small Group Waikiki Sunset Sailing Tour
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (116)

Small Group Waikiki Sunset Sailing Tour

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (116)
from
$99
Waikiki small group turtle snorkeling & sailing
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (103)

Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (103)
from
$99
Kona Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (307)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (307)
from
$98.10
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Oahu, USA
4.6 (41)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.6 (41)
from
$93.46
Sunset Sail Experience by Catamaran in Waikiki
Oahu, USA
4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (6)
from
$92.31
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Oahu, USA
4.8 (58)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.8 (58)
from
$90.01
Waikiki Sunset Cocktail Sail on the Moana Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (2,323)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (2,323)
from
$89.99
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Oahu, USA
4.8 (1,718)

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (1,718)
from
$89.56
Waikiki Turtle Snorkeling Tour with Free Pickup
Honolulu, USA
4.9 (277)

Waikiki Turtle Snorkeling Tour with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
4.9 (277)
from
$89
Waikiki Fireworks Cocktail Cruise
Oahu, USA
4.6 (9)

Waikiki Fireworks Cocktail Cruise

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (9)
from
$85.09
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Oahu, USA
4.8 (943)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (943)
from
$84.99
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (575)

Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (575)
from
$84.77

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

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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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Locate your Cool Hawaii Booking Number and the proof of the lower price you found.

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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.
  • Cool Hawaii promotions cannot be combined with the lowest price guarantee.
  • 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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