Big Island of Hawaii Sailing Trips

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Big Island of Hawaii Activities

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Kona Tradewind Catamaran Day Sail
4.8 (50)

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
4.8 (50)
from
$89
Kona Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.8 (345)

Kona Signature Catamaran Sunset Sail

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean...

1 hour 30 minutes • Free Cancellation
4.8 (345)
from
$109
Afternoon Sail & Snorkel to the Captain Cook Monument
4.9 (734)

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
4.9 (734)
from
$136
Afternoon Sail & Snorkel to the Captain Cook Monument
4.9 (252)

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
4.9 (252)
from
$136
Snorkel with Manta Rays Guaranteed
4.8 (743)

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
4.8 (743)
from
$141
Sunset and Manta Ray Snorkel Adventure
Likely to Sell Out
Likely to Sell Out
4.9 (855)

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
4.9 (855)
from
$155
Waikoloa Signature Catamaran Sunset Sail
Likely to Sell Out
Likely to Sell Out
4.8 (412)

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
4.8 (412)
from
$159
Deluxe Sail & Snorkel to the Captain Cook Monument
4.9 (577)

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
4.9 (577)
from
$179
Deluxe Sail & Snorkel to the Captain Cook Monument
4.9 (479)

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
4.9 (479)
from
$179
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Likely to Sell Out
Likely to Sell Out
5.0 (711)

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
5.0 (711)
from
$189
Waikoloa Catamaran Snorkel Sail Including Lunch
4.8 (108)

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
4.8 (108)
from
$189
Afternoon Ali'i Adventure
5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours • Free Cancellation
5.0 (6)
from
$276

Frequently Asked Questions

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

Recent activity reviews
A’hui hou
New York City
Waikoloa Signature Catamaran Sunset Sail
Karen_M, Sep 2026
A’hui hou
Fantastic!!! Crew and captain were attentive and personable.. drinks were plenty and food perfect.. I would do this again and again ! This time we were celebrating our 32nd wedding anniversary and it was perfect .. go here if you can ❤️🌋❤️🤙🤙
Read more
This was a great sunset...
New York City
Kona Signature Catamaran Sunset Sail
Johnny_G, Sep 2026
This was a great sunset...
This was a great sunset cruise. The captain and staff go all out to make your experience one to remember. Drinks and food were also amazing.
Read more
Our group of 8 had an...
New York City
Kona Signature Catamaran Sunset Sail
Anna_K, Sep 2026
Our group of 8 had an...
Our group of 8 had an amazing time on the sunset sail! Mike, our boat captain, was very friendly and made the experience very fun!
Read more
Sail and snorkel fun
New York City
Waikoloa Catamaran Snorkel Sail Including Lunch
Billyfo079, Sep 2026
Sail and snorkel fun
Great experience and great crew. Enjoyed all aspects of the tour.
Read more
10/10 manta day experience
New York City
Snorkel with Manta Rays Guaranteed
hj260898, Sep 2026
10/10 manta day experience
We were visiting from England and researched the most ethical and value for money tour, sea paradise came to the top of our searches. We received plenty of information prior to arriving, parking was located along Kaleiopapa road. We were greeted by an enthusiastic crew who made everyone feel comfortable. The manta ray experience was incredible! We were very lucky and saw dolphins as well as tuna during our snorkelling time. On the way back to the pier we were provided with drinks and an amazing view of the milkway. I would do this tour all over again if I had time. I would recommend this tour to anyone visiting Kailua Kona , it is a must do.
Read more
Fantastic sunset adventure
New York City
Waikoloa Signature Catamaran Sunset Sail
suelW5985QI, Sep 2026
Fantastic sunset adventure
Our catamaran cruise was beautiful and such a smooth ride. Crew was great and it even included a delicious dinner that was a surprise. We just expected snacks. Variety of cocktails were offered to meet everyone's tastes.
Read more
Great crew!
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
O2007RPnoelc, Sep 2026
Great crew!
My wife and I had a great time. Even though we had some trouble due to the hurricane approaching, the captain & crew did all the could to make the experience fun and get us in the water.
Read more
Amazing day snorkeling
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
tudmasterg, Sep 2026
Amazing day snorkeling
Absolutely awesome experience, the crew was soo friendly and helpful. We had a great day.
Read more
Funnest snorkel trip ever
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
tudmasterg, Sep 2026
Funnest snorkel trip ever
What an amazing fun day. The crew were friendly and took us to 2 awesome snorkeling spots. They also shared the history and facts about where we were. Captain Ed, Joshua and please forgive me, I can’t remember the woman’s name. A local and it started with K. She was so nice and helpful. I recommend 100%
Read more
Really nice day on the Sea Paradise Catamaran
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
GWBridgeNewYork, Sep 2026
Really nice day on the Sea Paradise Catamaran
An absolutely awesome snorkel/catamaran trip. The crew was amazing (Captain Jon and Crew Beau, Taylor, Austin, and I unfortunately forgot the name of the fourth one, a pleasant young lady). Along the way and back they take turns giving you the Hawaiian history of the sacred locations along the shore and what occurred there hundreds of years ago amongst the native Hawaiians and with Captain Cook. The two snorkel spots were teeming with fish. The crew were steady (but not overwhelming) in offering snacks and drinks, and turning on the showers for you after coming in from snorkeling. Captain Jon was either good (or lucky, LOL) in finding pods of spinner dolphins for us to watch. Lunch during the ride back was also pleasant. A nice sandwich bar. The staff assisted me in making a Hawaiian tuna wrap!
Read more
Fun time, crew was great...
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Marvin_R, Aug 2026
Fun time, crew was great...
Fun time, crew was great and very attentive. Snorkling was OK, saw plenty of fish, but not the best I have been to. We enjoyed listening to the history of the area and boat ride to and from.
Read more
Great fun!
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Kathleen_H, Aug 2026
Great fun!
It takes about 50 minutes to arrive to the snorkel area. We snorkeled 45-60 minutes and headed back. The crew was great, communicated the rules very well. They were friendly and did a great job. The boat is very nice and clean and offers 2 bathrooms.
Read more
Amazing
New York City
Afternoon Sail & Snorkel to the Captain Cook Monument
Makayla_T, Aug 2026
Amazing
Super fun and a beautiful place to snorkel! Everyone was super friendly and inviting. Had a fun and relaxing boat ride.
Read more
Snorkeling + island...
New York City
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Kiersten_M, Aug 2026
Snorkeling + island...
Snorkeling + island history + fabulous and energetic staff who are dedicated and clearly love their jobs
Read more
Worth of experience!!!
New York City
Snorkel with Manta Rays Guaranteed
Q4085LIsonjak, Aug 2026
Worth of experience!!!
Very touching experience! Everything from the reception, guidance, guides and at the end the dance of a large group of beautiful mantas! Go for it, you won’t be sorry.
Read more
Highly recommend a day on the Kona Tradewind Catamaran Day Sail
New York City
Kona Tradewind Catamaran Day Sail
Caroline_S, Aug 2026
Highly recommend a day on the Kona Tradewind Catamaran Day Sail
The crew was very family-friendly, accommodating and funny. The captain was kind to stop when we approached a pod of spinner dolphins and what a show! There were plenty of yummy options to choose from to drink and eat. The music also offered a nice touch. It was a nice way to start my staycation.
Read more
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