Hawaii Sailing Trips

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Hawaii Activities

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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
BYOB Friday Night Fireworks Cruise
Oahu, USA
5.0 (5)

BYOB Friday Night Fireworks Cruise

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (5)
from
$138.95
Maui Sunset Sail
Maui, USA
4.8 (209)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (209)
from
$137.82
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
Afternoon Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (251)

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (251)
from
$135.64
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
Maui Turtle Snorkel & Sail with Lunch & Open Bar
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (40)

Maui Turtle Snorkel & Sail with Lunch & Open Bar

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (40)
from
$122.40
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.5 (37)

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.5 (37)
from
$101.96
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
Luxury Catamaran Whale Watch
Maui, USA
4.9 (90)

Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (90)
from
$119
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
Honolulu, USA
5.0 (24)

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start...

4 hours • Hotel pickup offered • Free Cancellation
4 hours • Hotel pickup offered • Free Cancellation
4 hours • Hotel pickup offered • Free Cancellation
5.0 (24)
from
$119
'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
Akialoa Mā’alaea Sunset Sail
Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (21)

Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (21)
from
$108.11
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
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
Morning Whale Watch: Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (29)

Morning Whale Watch: 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
4.9 (29)
from
$100.22

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.

We Make It Easy!

Gather your information

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

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Email [email protected] with the documents, your name, and your home address.

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We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

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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