Hawaii Sailing Trips

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Hawaii Activities

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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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (240)

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
5.0 (240)
from
$50
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 …More

Oahu, USA
4.9 (988)

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
4.9 (988)
from
$55
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never …More

Oahu, USA
4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours • Free Cancellation
4.7 (1,265)
from
$53
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 …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (96)

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
4.9 (96)
from
$159
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 …More

Big Island of Hawaii, USA
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
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 …More

Oahu, USA
4.9 (210)

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
4.9 (210)
from
$62
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 …More

Maui, USA
4.8 (830)

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
4.8 (830)
from
$213
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 …More

Big Island of Hawaii, USA
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
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 …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.8 (349)

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
4.8 (349)
from
$89
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 …More

Big Island of Hawaii, USA
4.9 (578)

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 (578)
from
$179
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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (127)

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
4.9 (127)
from
$250
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 …More

Likely to Sell Out
Likely to Sell Out
Honolulu, USA
4.9 (110)

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
4.9 (110)
from
$100
'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 …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (195)

'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
5.0 (195)
from
$117
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), …More

Honolulu, USA
4.9 (446)

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP),...

3 hours • Hotel pickup offered • Free Cancellation
4.9 (446)
from
$90
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 …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (34)

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
5.0 (34)
from
$102
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 …More

Big Island of Hawaii, USA
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

Frequently Asked Questions

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

Recent activity reviews
So worth the cost , crew...
New York City
Day’s End Cocktail Sunset Sail
Brenda_R, Sep 2026
So worth the cost , crew...
So worth the cost , crew were friendly, helpful very attentive to everyone & Captain Jordan knew her stuff! Captain kept us in the best water since the wind was very strong, I felt very comfortable the whole ride. Highly recommend!
Read more
Fabulous time!
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
donnabY1972HD, Sep 2026
Fabulous time!
Great time. Lots of turtles! The crew was great and Dustin was the best!
Read more
Snorkeling
New York City
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup
deannw861, Sep 2026
Snorkeling
Great excursion with exceptional guides especially Dustin and Noah and Rowan.
Read more
Wonderful evening!
New York City
Paragon Lahaina Sunset Sail
Sharon_M, Sep 2026
Wonderful evening!
This was such a great sunset sail! The entire experience was perfect. The staff was very attentive throughout the entire evening. This was our favorite activity we did while in Maui!
Read more
Sunset fun
New York City
‘Alihilani Lahaina Sunset Sail
Ramiro_F, Sep 2026
Sunset fun
Great crew, Great cruise. Recommend highly. Made great friends and crew made sure everyone was taken care off.
Read more
Sea turtles catamaran tour
New York City
Waikiki Turtle Snorkeling Adventure(8am)
250bluef, Sep 2026
Sea turtles catamaran tour
A must do experience snorkeling with the sea turtles and so many different fish
Read more
The experience was...
New York City
Waikiki Sunset Boat Cruise
Jay_P, Sep 2026
The experience was...
The experience was relaxing and beautiful! We were provided with a complimentary drink and snack. Good hosts!
Read more
Experience that lives up to the hype + plused by the crew
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jason_H, Sep 2026
Experience that lives up to the hype + plused by the crew
Great for families with small kids. Not overbooked, great boat and accommodations, multiple ways for young kids to engage in the experience - life vests, floating vessels, placards to pinpoint wildlife, etc. crew was very engaging, personable, and caters to our family needs. Even let the kids "drive" the boat. Couldn't recommend more.
Read more
Relaxing cruise
New York City
Waikiki Sunset Boat Cruise
Michal_Z, Sep 2026
Relaxing cruise
It was calm almost like privatr cruise with good music and good ladies. We saw beautiful rainbow and sunset.
Read more
Lovely Maui Experience
New York City
‘Alihilani Lahaina Sunset Sail
laurazD7578IN, Sep 2026
Lovely Maui Experience
Jess Jen and Brayden were wonderful hosts. The food and drinks were great. It was a relaxing and fun evening.
Read more
Amazing snorkeling experience!
New York City
Waikiki Turtle Snorkeling Adventure(8am)
gehroup, Sep 2026
Amazing snorkeling experience!
I had an amazing time snorkeling! The experiences was so much fun, and I got to see lots of fish and sea turtles. The whole experience was unforgettable. I would definitely recommend this to anyone looking for a fun adventure!
Read more
So kind and accommodating...
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
Minerva_L, Sep 2026
So kind and accommodating...
So kind and accommodating i would highly recommend!!! We got to see turtles, dolphins and different fishes.
Read more
Snorkeling with the turtles
New York City
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
O5530DDrussellm, Sep 2026
Snorkeling with the turtles
Great crew and guides. We saw three turtles while out as well as dolphins and variety of fish.
Read more
Great day snorkeling
New York City
Deluxe Sail & Snorkel to the Captain Cook Monument
ShellyM926, Sep 2026
Great day snorkeling
We had a wonderful time with two snorkeling stops. We felt that we had plenty of time to snorkel at each. We also enjoyed our snorkel break when the captain took us on a sailing trip and we found dolphins. The continental breakfast and lunch (sandwich) was also quality. The bathroom on the boat was very clean and modern.
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
Fantastic Evening On the Water
New York City
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Raewyn_B, Sep 2026
Fantastic Evening On the Water
We had a wonderful time out on the water! The music was great- plenty of drinks & the crew made sure we were all looked after🍹The sunset was amazing - a fabulous memory to take home from Honolulu🌅
Read more
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