Hawaii Sailing Trips

104 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
48
52
46
Duration Clear
3
91
16
0
0
Price Clear
$0 $500+
Rating Clear
90
100
102
Specials Clear
104
42
0
17
2
Features Clear
5
79
88
4
90
2
Accessibility Clear
0
31
82
Families Clear
79
26
48

Hawaii Activities

Attractions

Guides

Calendar

Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (211)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (211)
from
$50
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
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
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
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
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Oahu, USA
4.9 (960)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (960)
from
$54.98
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
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Oahu, USA
4.9 (202)

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (202)
from
$61.50
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
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.8 (327)

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (327)
from
$84.15
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
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
Kona Tradewind Catamaran Day Sail
Big Island of Hawaii, USA
4.8 (49)

Kona Tradewind Catamaran Day Sail

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (49)
from
$80.10
Waikiki Turtle Snorkeling Adventure(8am)
Likely to Sell Out
Likely to Sell Out
Honolulu, USA
5.0 (83)

Waikiki Turtle Snorkeling Adventure(8am)

Discover an all-in-one Waikiki ocean adventure with our Turtle Snorkeling Tour. Cruise aboard our spacious and comfortable catamaran to Turtle Canyon, where you’ll have the...

3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
3 hours • Hotel pickup offered • Free Cancellation
5.0 (83)
from
$100
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
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

Frequently Asked Questions

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

Hawaii Activities
Attractions
Guides
Calendar
View more
View more
Language
Currency

Site Settings

Activity name

Currency

Activity name

Lowest Price Guarantee

Activity name

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.

Send it to us

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

We'll review

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

Activity name

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.

Cool Support

Ask us anything!

Activity name

Cool Robot