Hawaii Sailing Trips

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Hawaii Activities

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Waikiki private Day Tour and Sunset sail for couples
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$300
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
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (59)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (59)
from
$289
Afternoon Ali'i Adventure
Big Island of Hawaii, USA
5.0 (6)

Afternoon Ali'i Adventure

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,...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (6)
from
$276
Kauai: Leila Na Pali Sunset Dinner Sail
Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.8 (553)

Kauai: Leila Na Pali Sunset Dinner Sail

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...

4 to 5 hours • Free Cancellation
4 to 5 hours • Free Cancellation
4 to 5 hours • Free Cancellation
4.8 (553)
from
$263.82
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (18)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (18)
from
$251.10
Polynesian Canoe Sunset Sail
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (125)

Polynesian Canoe Sunset Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (125)
from
$250
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
Oahu, USA
4.8 (34)

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (34)
from
$249.99
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Maui, USA
5.0 (127)

Half-Day Deluxe Molokini Snorkel Excursion in Maui

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (127)
from
$249
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
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Maui, USA
5.0 (66)

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (66)
from
$216.22
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
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Maui, USA
5.0 (26)

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (26)
from
$203.16
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
Maui, USA
4.9 (218)

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.9 (218)
from
$200
Polynesian Canoe Day Sail
Oahu, USA
5.0 (28)

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (28)
from
$200
Polynesian Canoe Morning Sail
Oahu, USA
5.0 (18)

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (18)
from
$200

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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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).
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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.
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  • 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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