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 Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Hawaii's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. …More

Oahu, USA
4.9 (1,743)

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Hawaii's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki....

2 hours • Free Cancellation
4.9 (1,743)
from
$50
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far …More

Oahu, USA
4.9 (261)

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far...

2 hours • Free Cancellation
4.9 (261)
from
$50
Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (24)

Sunset sail Aboard Manakai Catamaran

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a...

1 hour 30 minutes • Free Cancellation
5.0 (24)
from
$50
South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have …More

Oahu, USA
4.8 (26)

South Shore Open Sail from Kewalo Harbor Including Drinks

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have...

1 hour 30 minutes • Free Cancellation
4.8 (26)
from
$48
Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point …More

Oahu, USA
4.8 (75)

Waikiki Sunset Cruise from Oahu

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point...

2 hours • Free Cancellation
4.8 (75)
from
$45

Frequently Asked Questions

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

Recent activity reviews
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
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
Awesome trip
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
leeaY7148QU, Sep 2026
Awesome trip
Wonderful experienced crew and clean boat. Definitely a recommend for those who are new to snorkeling. 10/10 would use again the next time we’re here.
Read more
Lucy, Liza & Crash were...
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Carlos_T, Sep 2026
Lucy, Liza & Crash were...
Lucy, Liza & Crash were amazing ! it was well worth it. they were friendly, funny and very knowledgable.
Read more
Loved it!
New York City
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
tonih616, Sep 2026
Loved it!
They were wonderful! Everyone was friendly and knowledgable, and we had a lot of fun. We will definitely book again!
Read more
Golden Hours
New York City
Waikiki Sunset Cruise from Oahu
Gin_T, Sep 2026
Golden Hours
It’s a great experience and kindest staffs are Surrounded. Unique view of sunsets moment with co workers and others are golden hours.
Read more
Sunset boat ride
New York City
Waikiki Sunset Cruise from Oahu
Tory_P, Sep 2026
Sunset boat ride
It was such a wonderful sunset boat ride! It was beautiful ! Me and my boyfriend thoroughly enjoyed our time!
Read more
Great time!!!
New York City
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
Q7130NUnicolec, Sep 2026
Great time!!!
So fun!!!!! Great crew. Great energy.
Read more
Great time on the high sea
New York City
South Shore Open Sail from Kewalo Harbor Including Drinks
Johnathan_W, Aug 2026
Great time on the high sea
It was fun and the crew is great, the boat is beautiful. The captain dropped the sails and we took off like a rocket.
Read more
Great Sunset Cruise
New York City
Sunset sail Aboard Manakai Catamaran
Kathie_L, Aug 2026
Great Sunset Cruise
We did this sunset cruise to celebrate our daughter’s birthday and it was wonderful. There are 10 in our family and everyone had a great time. All the crew members were very well trained and friendly.
Read more
Highlight of our trip thus far!
New York City
Sunset sail Aboard Manakai Catamaran
briannalP5105FK, Jul 2026
Highlight of our trip thus far!
What an amazing experience! Woody, Sophia, and Cameron were excellent guides and made the trip that much better. We met on the shore behind the Duke statue which was super easy to find and very accessible. To be on the water and see Waikiki is a once in a lifetime experience. Thank you again!
Read more
A beautiful day on the water.
New York City
South Shore Open Sail from Kewalo Harbor Including Drinks
judogayle, Jun 2026
A beautiful day on the water.
The free drinks were a hit. My daughter enjoyed her soda. The crew were very professional yet friendly and helpful. I would like to have less music and more just the quiet sounds of the sails and ocean. Not everyone likes loud music!
Read more
Great views, friendly and worth it
New York City
Waikiki Sunset Boat Cruise
daisycK9204HL, Sep 2026
Great views, friendly and worth it
This was money well spent! The crew was very nice and really appreciated the hospitality and punctuality. The views were fantastic no bad seats on the boat! Snacks and juice were nice perk too! Def recommend booking!
Read more
Beautiful sunset
New York City
Waikiki Sunset Boat Cruise
Yacaranday_A, Sep 2026
Beautiful sunset
AMAZING! Sunset was wonderful, the crew gave the most amazing hospitality and really felt the warm family fun vibes with them. 10/10 sunset cruise!
Read more
Krash, Lucy and Tony are amazing!
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Erick_R, Sep 2026
Krash, Lucy and Tony are amazing!
The snorkeling trip was amazing: we had fun and saw several turtles and lots of fish. Krishna, Lucy and Tony were fantastic hosts - we felt save and they made it fun for us. I highly recommend it. DON'T GO ON ANY OTHER BOAT.
Read more
Fantastic experience!
New York City
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
joshuawY2463QS, Sep 2026
Fantastic experience!
Great knowledgeable crew. Had a fantastic time!
Read more
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