Hawaii Sailing Trips

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Hawaii Activities

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Turtles & Tacos Luxury Catamaran Snorkel
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (146)

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.8 (146)
from
$199
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
Honolulu, USA
4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
5 hours 30 minutes • Hotel pickup offered • Free Cancellation
5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
from
$196.63
Snorkel Sail Adventure off Ka'anapali Beach in Maui
Lahaina, USA
5.0 (45)

Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (45)
from
$192.17
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
Waikoloa Catamaran Snorkel Sail Including Lunch
Big Island of Hawaii, USA
4.8 (107)

Waikoloa Catamaran Snorkel Sail Including Lunch

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.8 (107)
from
$189
Honolua Snorkel Sail from Lahaina
Maui, USA
5.0 (58)

Honolua Snorkel Sail from Lahaina

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (58)
from
$180.92
Hawaiian Canoe Sailing Experience in Maui
Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (59)

Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (59)
from
$179
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
Deluxe Sail & Snorkel to the Captain Cook Monument
Big Island of Hawaii, USA
4.9 (476)

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 Cook Monument"...

4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4.9 (476)
from
$178.72
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
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
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
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
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
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

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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 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.
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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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