Hawaii Sailing Trips

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Hawaii Activities

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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
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
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
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
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
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
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, …More

Oahu, USA
4.9 (255)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes • Free Cancellation
4.9 (255)
from
$53
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while …More

Oahu, USA
5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$53
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 Sunset Sailing Catamaran Swim and Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the …More

Oahu, USA
4.8 (595)

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours • Free Cancellation
4.8 (595)
from
$56
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take …More

Maui, USA
3.5 (4)

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
3.5 (4)
from
$60
Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA
4.7 (30)

Waikiki Friday Night Fireworks Cruise

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour • Free Cancellation
4.7 (30)
from
$60
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
Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide …More

Oahu, USA
5.0 (4)

Waikiki Sunset Cruise and Iconic Views with Swimming

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide...

2 hours • Free Cancellation
5.0 (4)
from
$65
Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden …More

Oahu, USA
4.6 (87)

Waikiki 2 Hour Sunset Whale Watching Cruise Sightings Guaranteed

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden...

2 hours • Free Cancellation
4.6 (87)
from
$68

Frequently Asked Questions

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

Recent activity reviews
Amazing sail & sunset cruise!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Dama_M, Sep 2026
Amazing sail & sunset cruise!
Great sunset cruise! The crew was very helpful & friendly-Alex, Alejandro & Jandy❤️ I would definitely go again🌊😊
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
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
Dream Sailing!
New York City
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
Colleen_E, Sep 2026
Dream Sailing!
Phenomenal experience. Capt Mo, John, & Kai were wonderful & entertaining. We felt so confident with their seamanship and safe with thier knowledge of the area and Swim precautions at the same time they made it a fun and humorous adventure. Little Dog stole the show though! Mahalo for a wonderful time!
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
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
Waikīkī afternoon sailing
New York City
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu – Best Value
karenwbrisbane, Sep 2026
Waikīkī afternoon sailing
10/10 all the way. Such an unforgettable experience. Pre wedding celebration afternoon sail went out from the beach to the deep blue waters off Waikiki where we enjoyed drinks and took in the stunning views. The crew were all welcoming and ensured we had a great time.
Read more
Awesome Laid-back sunset cruise
New York City
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
Kim_U, Sep 2026
Awesome Laid-back sunset cruise
Wonderful relaxing experience at great price! Excellent crew! Very helpful and pleasant! Surprise charcuterie snackboard! Highly recommend if your laid back.
Read more
It made us feel happy
New York City
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
163JaneS, Sep 2026
It made us feel happy
We took this amazing catamaran ride on our last day on Oahu, and what a highlight of the trip it was! Of course, the perfect weather contributed to the fun. But the crew, the views, the music and the drinks were outstanding. We enjoyed every minute of it. Do it by all means, and you won’t regret it.
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
Fun Trip! Great for photo taking!
New York City
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
laneowyang, Sep 2026
Fun Trip! Great for photo taking!
very helpful crew! I was having a foot problem and the crew made sure i got on and off safely. Wish there were benches to sit on while wating for the ship.
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
Good times
New York City
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu – Best Value
T9716AEwendyb, Sep 2026
Good times
Met a great friend there, love my experiences with Holokai 🤗🤗🤗🤗
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
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