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Top Hawaii Sailing Trips

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Hawaii Tours

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Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (1,463)

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either...

2 hours • Free Cancellation
4.8 (1,463)
from
$81
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for …More

Oahu, USA
4.8 (947)

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for...

2 hours 30 minutes • Free Cancellation
4.8 (947)
from
$85
Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (2,368)

Waikiki Sunset Cocktail Sail on the Moana Catamaran

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with...

2 hours • Free Cancellation
4.9 (2,368)
from
$90
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (591)

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

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time...

1 hour 30 minutes • Free Cancellation
4.8 (591)
from
$85
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island …More

Oahu, USA
4.8 (1,740)

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island...

2 hours 30 minutes • Free Cancellation
4.8 (1,740)
from
$90
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 (2,101)

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 (2,101)
from
$99
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
Kauai: Leila Na Pali Sunset Dinner Sail

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.8 (563)

Kauai: Leila Na Pali Sunset Dinner Sail

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa...

4 to 5 hours • Free Cancellation
4.8 (563)
from
$264
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 …More

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
4.8 (413)

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 (413)
from
$159
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 …More

Big Island of Hawaii, USA
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
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
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
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 …More

Big Island of Hawaii, USA
5.0 (712)

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 (712)
from
$189
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look …More

Kauai, USA
4.8 (1,544)

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look...

5 hours • Free Cancellation
4.8 (1,544)
from
$223
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Experience one Cool Destinations'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 Destinations'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
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

Maui, USA
5.0 (131)

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours • Free Cancellation
5.0 (131)
from
$306
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Destinations 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 Destinations 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
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 (243)

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 (243)
from
$50
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

Frequently Asked Questions

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

Recent tour reviews
Fantastic Sunset Cruise
New York City
Waikiki Sunset Cocktail Sail on the Moana Catamaran
Helene_L, Sep 2026
Fantastic Sunset Cruise
From the moment we arrived at the pier, the experience was top notch. Highly recommend the VIP ticket option. Crew was very attentive and took time with every guest. The ride was comfortable and the sunset was amazing.
Read more
Perfect last minute sunset cruise
New York City
Waikiki Sunset Boat Cruise
Steve_J, Sep 2026
Perfect last minute sunset cruise
Laney welcomed me as soon as I arrived. Funny-- we had similar sunglasses. Totally twinning!!! Soon thereafter we met Mary the Captain. I knew from the first "Wicked Awesome" that we were in for a real treat. Laney and Mary took us out of the Harbor and headed towards Diamond Head. It was a beautiful day with just a few clouds in the sky. I set up front with a couple from Minnesota and another from Mexico. I was traveling solo as my wife had to work late. Mary took us towards Diamond head but the ocean was getting a little rough so we only made it about 60% there. Laney continued to check on all of us through the tour and I had a nice chat with Captain Mary about life on HI. About half way through, Laney came around and took pictures for everyone. On the way back, Laney offered us chips in addition to the canned tropical juices she offered before we took off. After the tour was over, Laney laid out all our shoes on the dock (you have to take them off on the boat). Between the two of them, I felt well taken care of and super safe on the boat. I would definitely recommend and will be going again in a couple of weeks when I come back with my wife for work. Thanks guys!
Read more
Sunset cruise
New York City
Waikiki Sunset Boat Cruise
Maureen_P, Sep 2026
Sunset cruise
Great time. View of the sunset was spectacular. Both Mary and Madeline were great hosts. (Unsure of names ) Loved the music and snacks. You will enjoy yourself!
Read more
super!!
New York City
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
vapsiv2026, Sep 2026
super!!
had a amazing time and experience the crew was very friendly , thanks to jenna, anthony, sofia and kemina.
Read more
A must do!
New York City
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Leandra_R, Sep 2026
A must do!
Incredible experience. Honestly the highlight of our trip. The staff was friendly and the experience was incredible we saw so many turtles.
Read more
So easy to get on and off...
New York City
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
Susan_S, Sep 2026
So easy to get on and off...
So easy to get on and off the boat. Captain and crew were helpful. Would book with this tour company again
Read more
Perfect Sunset Cruise with Family & Friends
New York City
Waikiki Sunset Cocktail Sail on the Moana Catamaran
timmyh722, Sep 2026
Perfect Sunset Cruise with Family & Friends
★★★★★We had an absolutely fantastic time on our sunset cruise with Moana Sailing! There were 10 of us—family and friends—and it ended up being one of the highlights of our Hawaii trip.From start to finish, the crew was outstanding. They were friendly, attentive, fun, and made sure everyone in our group was comfortable and having a great time. The drinks were good, the atmosphere was relaxed, and being out on the water together was exactly what we were hoping for.And the sunset—wow! We could not have asked for a better evening. The weather was beautiful, the ocean was gorgeous, and watching the sun go down from the boat was absolutely spectacular. We got some incredible photos and, more importantly, made some great memories together.If you’re visiting Waikiki and looking for a fun sunset cruise with family or friends, Moana Sailing is definitely worth doing. Great crew, great drinks, perfect weather, an unbelievable sunset, and an all-around fantastic experience. We would absolutely do it again!
Read more
Turtles!!!
New York City
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
djwaterhouse, Sep 2026
Turtles!!!
Anthony, Clay and Natalie were GREAT!
Read more
Great Experience
New York City
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
K6723FPhannahs, Sep 2026
Great Experience
We loved going on this catamaran with Captain Mo and her team. They were so accommodating and polite. They explained everything we were going to do and how to do it. They are great with having kids on board. I highly recommend!!
Read more
A wonderful snorkel experience
New York City
Molokini Crater Deluxe Snorkel and Sail – Half Day Excursion
Coastal615738, Sep 2026
A wonderful snorkel experience
The crew on the Ali’i Nui was fantastic. They were informative, personable, and kind. They didn’t hesitate to help when needed. Instructions were clear and we spent an adequate amount of time in the water seeing plenty of fish and turtles! Service for drinks was quick, and the food was plentiful. I had a great experience!
Read more
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
Amazing as always! We do...
New York City
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
Jason_G, Sep 2026
Amazing as always! We do...
Amazing as always! We do this sailing every time we are in Honolulu and it’s always great. Good drinks, gorgeous views, and an awesome crew. Highly recommend!
Read more
Romantic sunset cruise.
New York City
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
705jeffu, Sep 2026
Romantic sunset cruise.
This was a great experience. We attended on a Friday which is 21 and over. The provided punch was very good. The sunset was gorgeous and everyone seemed to have a great time.
Read more
Turtles and sailing
New York City
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
jengay2018, Sep 2026
Turtles and sailing
The crew (Carlos, Des, Julia and Tommy) were amazing and made it a wonderful experience. We saw several turtles and had a great time
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
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
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