Hawaii Sailing Trips

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Hawaii Activities

Attractions

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Sunset sail Aboard Manakai Catamaran
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (23)

Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (23)
from
$49.82
Paragon Lahaina Sunset Sail
Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (23)

Paragon Lahaina Sunset Sail

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (23)
from
$102
Private Oahu Sunset Charter with Tasting and Drinks
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (52)

Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes • Free Cancellation
120 to 150 minutes • Free Cancellation
120 to 150 minutes • Free Cancellation
5.0 (52)
from
$1,413.61
Waikiki Sunset Cruise from Oahu
Oahu, USA
4.8 (68)

Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (68)
from
$45
Friday Night Firework Cruise in Waikiki
Oahu, USA
4.8 (34)

Friday Night Firework Cruise in Waikiki

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline,...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.8 (34)
from
$69.99
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
Waikiki Heritage and Diamond Head Wildlife Sail
Oahu, USA
4.8 (31)

Waikiki Heritage and Diamond Head Wildlife Sail

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore,...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (31)
from
$119
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
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
Maui, USA
3.5 (4)

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
3.5 (4)
from
$59.95
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (306)

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (306)
from
$72.96
Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (210)

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (210)
from
$79
Midday Whale Watch: Mā’alaea Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (103)

Midday Whale Watch: Mā’alaea 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
4.9 (103)
from
$100.22
'Alihilani Lahaina Sunset Sail
Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (177)

'Alihilani Lahaina Sunset Sail

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (177)
from
$117.30
2-Hour Oahu Sunset Catamaran Sail
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (134)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (134)
from
$130
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

Frequently Asked Questions

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

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  • 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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  • 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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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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