Hawaii Sailing Trips

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Hawaii Activities

Attractions

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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
Maui Turtle Snorkel & Sail with Lunch & Open Bar
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
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
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
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
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
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
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.6 (66)

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (66)
from
$141.98
Moana’s Luxury semi-private Sunset Cruise on Nalu
Oahu, USA
5.0 (17)

Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$149.99
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
Waikoloa Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (409)

Waikoloa Signature Catamaran Sunset Sail

End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers...

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
4.8 (409)
from
$159
Day's End Cocktail Sunset Sail
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (91)

Day's End Cocktail Sunset Sail

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (91)
from
$159
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Maui, USA
4.9 (111)

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.9 (111)
from
$163.20
Sound of the Ocean Whale Watch Sail
Maui, USA
5.0 (1)

Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (1)
from
$163.68
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

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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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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