Hawaii Sailing Trips

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Hawaii Activities

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Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, …More

Oahu, USA
4.8 (62)

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night,...

1 hour • Free Cancellation
4.8 (62)
from
$90
Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu …More

Oahu, USA
4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hours • Free Cancellation
4.8 (6)
from
$92
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and …More

Oahu, USA
4.7 (2,100)

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and...

2 to 3 hours • Free Cancellation
4.7 (2,100)
from
$99
Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (118)

Small Group Waikiki Sunset Sailing Tour

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come...

2 hours • Free Cancellation
4.9 (118)
from
$99
Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (105)

Waikiki small group turtle snorkeling & sailing

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of...

2 hours • Free Cancellation
5.0 (105)
from
$99
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
Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (103)

Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.9 (103)
from
$100
Morning Whale Watch: Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.9 (29)

Morning Whale Watch: Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.9 (29)
from
$100
Afternoon Sail With the Whales from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (1)

Afternoon Sail With the Whales from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
5.0 (1)
from
$100
Midmorning Whale Watch from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.5 (2)

Midmorning Whale Watch from Lahaina Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.5 (2)
from
$100
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
Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (36)

Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque...

2 hours • Free Cancellation
5.0 (36)
from
$108
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 …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (349)

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 (349)
from
$109
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise …More

Oahu, USA
4.5 (47)

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise...

2 hours 30 minutes • Free Cancellation
4.5 (47)
from
$110
Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and …More

Maui, USA
4.8 (85)

Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours • Free Cancellation
4.8 (85)
from
$112
'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

Frequently Asked Questions

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

Recent activity reviews
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
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
Friendly fun!
New York City
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
David_G, Sep 2026
Friendly fun!
We booked a last minute trip to go see the turtles after a hurricane. The sights weren't awesome because the sea was murkey. But the crew was amazing. They took great care of us. They made sure everybody had something to eat. Something to drink and tried their best to show us turtles. We did see a couple and they assured us that we would normally see more in better weather. We would totally recommend Capt. Anthony and Sophia. And Sofia, again, they were absolutely outstanding.
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
Excellent tour and experience
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
P8063NGpaula, Sep 2026
Excellent tour and experience
Excelllent communication. Our original tour date was cancelled and we were offered a full refund or we could rebook for another day. Glad we rebooked. The experience was perfect. The tour guides were friendly and professional.
Read more
Beautiful weather and sunset 🌅
New York City
Kona Signature Catamaran Sunset Sail
danieljS6776VI, Sep 2026
Beautiful weather and sunset 🌅
Had an AMAZING experience! We highly recommend this experience.
Read more
Sunset Sail was the best!
New York City
Kona Signature Catamaran Sunset Sail
Nancy_R, Sep 2026
Sunset Sail was the best!
Staff was helpful, polite and made the cruise fun. The bar drinks were great and the teriyaki chicken and rice were tasty
Read more
Awesome!
New York City
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Jennifer_A, Sep 2026
Awesome!
This was incredible! If I could do it again I would but would book for longer! Guides/crew were so nice too! 10 out of 10!
Read more
Sunset cruise Maui
New York City
Akialoa Mā’alaea Sunset Sail
Carol_S, Sep 2026
Sunset cruise Maui
We really enjoyed our sunset cruise. The staff was very attentive and entertaining! If we’d time, we would’ve done this excursion a second time! Thank you to Brandon, Matt and Megan!
Read more
Perfect sail, incredible crew
New York City
Paragon Lahaina Sunset Sail
O2646KJellies, Sep 2026
Perfect sail, incredible crew
Really great experience for the price! We had such a perfect evening and the crew was incredible. would highly recommended
Read more
No Worries
New York City
Akialoa Mā’alaea Sunset Sail
Todd_J, Sep 2026
No Worries
Great experience, a real friendly crew, light hearted atmosphere and really great music. Highly recommend outing.👍👍
Read more
The Best!
New York City
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Cristina_S, Sep 2026
The Best!
Fantastic crew and captain (captain nick, crewmates nick, and mike?). They quite literally sprang into action when a passenger got injured in the water by a jelly fish. I have never felt more safe, secure, and well taken care of during this excursion. I’d would use this company with this crew anytime time I’m back again on the island. Great experience and fun!
Read more
Great night out
New York City
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Hydes2014, Sep 2026
Great night out
Ava and the guys were great. Always walking around making sure we were having a good time and made sure we had a fresh drink.
Read more
Fun thing to do on a Friday night on Waikiki Beach
New York City
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Howardru, Sep 2026
Fun thing to do on a Friday night on Waikiki Beach
Fun 90 minutes on a catamaran ride away from the beach to watch the fireworks go off. The crew was fun and entertaining. The drinks were not bad either. A nice election a beer wines and Hawaiian drinks fireworks lasted only five minutes but a fun thing to do to see from the actual ocean. My wife was happy that she got to wear her specialized sweatshirt just for the occasion 😊
Read more
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