Hawaii Sailing Trips

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Hawaii Activities

Attractions

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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
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Oahu, USA
4.9 (1,706)

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

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 Waikiki....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,706)
from
$59.99
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Kauai, USA
4.8 (1,533)

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

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...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.8 (1,533)
from
$222.86
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (1,445)

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (1,445)
from
$80.71
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Oahu, USA
4.9 (960)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (960)
from
$54.98
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
Sunset and Manta Ray Snorkel Adventure
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.9 (854)

Sunset and Manta Ray Snorkel Adventure

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...

2 hours 15 minutes • Free Cancellation
2 hours 15 minutes • Free Cancellation
2 hours 15 minutes • Free Cancellation
4.9 (854)
from
$154.51
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Maui, USA
4.8 (823)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.8 (823)
from
$213.41
Snorkel with Manta Rays Guaranteed
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (740)

Snorkel with Manta Rays Guaranteed

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...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (740)
from
$141.03
Afternoon Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (732)

Afternoon Sail & Snorkel to the Captain Cook Monument

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (732)
from
$135.64
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Big Island of Hawaii, USA
5.0 (710)

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

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...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (710)
from
$189
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
Oahu, USA
4.8 (583)

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (583)
from
$56
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
Deluxe Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (571)

Deluxe Sail & Snorkel to the Captain Cook Monument

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...

4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4.9 (571)
from
$178.72
Kauai’s Na Pali Coast Snorkel and Sail Tour
Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.9 (556)

Kauai’s Na Pali Coast Snorkel and Sail Tour

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making...

6 hours • Free Cancellation
6 hours • Free Cancellation
6 hours • Free Cancellation
4.9 (556)
from
$292.48

Frequently Asked Questions

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

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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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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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