Hawaii Sailing Trips

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Hawaii Activities

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Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and …More

Maui, USA
4.8 (158)

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours • Free Cancellation
4.8 (158)
from
$199
2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.9 (138)

2-Hour Oahu Sunset Catamaran Sail

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu....

2 hours • Free Cancellation
4.9 (138)
from
$130
Half-Day Deluxe Molokini Snorkel Excursion in Maui

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)

Half-Day Deluxe Molokini Snorkel Excursion in Maui

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
$290
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, …More

Maui, USA
5.0 (130)

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers,...

5 hours • Free Cancellation
5.0 (130)
from
$163
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
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 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
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
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
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
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
Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way …More

Maui, USA
4.9 (90)

Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours • Free Cancellation
4.9 (90)
from
$119
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
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based …More

Maui, USA
5.0 (79)

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours • Free Cancellation
5.0 (79)
from
$216
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
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

Frequently Asked Questions

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

Recent activity reviews
A wonderful snorkel experience
New York City
Half-Day Deluxe Molokini Snorkel Excursion in Maui
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
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
Great sunset cruise from Ko'Olina
New York City
2-Hour Oahu Sunset Catamaran Sail
craigandt, Sep 2026
Great sunset cruise from Ko'Olina
Fantastic crew and evening trip. Location is great for MVCI guests and owners and a short walk away. The staff was friendly, the weather was great and we had a fantastic time.For guests at MVCI - this is a must do for your trip!
Read more
Best excursion in Hawaii
New York City
Turtles & Tacos Luxury Catamaran Snorkel
Gregory_h, Sep 2026
Best excursion in Hawaii
This was by far my favorite excursion that we did while we were in Hawaii. Very professional and wonderful crew. We had a blast.
Read more
We had so much fun! The...
New York City
Turtles & Tacos Luxury Catamaran Snorkel
Kimi_H, Sep 2026
We had so much fun! The...
We had so much fun! The crew was very helpful and kind, the food was delicious, and we saw so many turtles! We had such a great time snorkeling that we wish we had a little more time in the water, but that did not take away from our overall experience!
Read more
Great Lanai experience with Trilogy
New York City
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
petagayg2024, Sep 2026
Great Lanai experience with Trilogy
We were referred by a friend who takes her family on Trilogy every year. So glad we went with her recommendation. The crew was great and very friendly. Very nice catamaran with plenty of seating and shade on board. We had our own snorkeling gear but they had plenty on board for everyone. The snorkeling experience by Lanai was beautiful. Very grateful that the Trilogy crew facilitated such a memorable experience.
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
A Great Snorkel Adventure!
New York City
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
jacquelinemE6692OR, Sep 2026
A Great Snorkel Adventure!
We set sail on the Alihilani on a beautiful morning! The staff greeted us with a yummy continental breakfast. After reaching our snorkeling destination, we were given our equipment and important information we needed for a safe experience. A staff member came out into the water and kept a “lookout” while sitting on a surfboard. This gave us a good feeling of security. What fantastic colorful fish we saw among the beautiful coral and blue sand! After snorkeling we were treated to a delicious lunch of chicken, fried rice and vegetables! Yum! The open bar was a fun perk too!! Captain Kevin and his crew gave my husband and I a wonderful day!
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
Amazing sunset cruise
New York City
2-Hour Oahu Sunset Catamaran Sail
450halc, Sep 2026
Amazing sunset cruise
We had an amazing time on the sunset sail. What a great way to watch a beautiful Hawaiian sunset. Elijah, Jake, and Miriam were an excellent crew. They were attentive and made the tour a great one. We would highly recommend this tour
Read more
An Amazing Experience with Sail Maui!
New York City
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
hongc884, Sep 2026
An Amazing Experience with Sail Maui!
⭐⭐⭐⭐⭐ An Amazing Experience with Sail Maui!I had such an incredible experience with Sail Maui on September 15th on the snorkeling trip to Lanai. Honestly, this was one of the highlights of my Hawaii trip, and it was worth every penny!The crew was absolutely amazing. They were friendly, welcoming, attentive, and genuinely caring. I became a little seasick during the trip but didn’t tell anyone. I thought I would just lie down on the nets and wait for it to pass. Somehow, the crew noticed that I wasn’t feeling well and immediately came to check on me.They offered me a ginger chew, an ice bag to hold, and medicine. The ginger chew and ice bag worked wonderfully! They continued checking on me frequently and kept offering me drinks to make sure I was comfortable. I was so impressed by how observant and thoughtful they were. They didn’t just provide good service—they truly cared about how I was feeling.And the snorkeling was spectacular! The water was beautiful and incredibly clear. We saw so many colorful fish, sea turtles, and beautiful coral reefs. It was an amazing experience to see all of that underwater.Then came another unforgettable moment: the captain stopped the boat so we could watch dolphins playing right in front of us! Seeing them so close, swimming and playing in the ocean, was absolutely magical. 🐬From beginning to end, everything was wonderful—the beautiful ocean, incredible snorkeling, amazing wildlife, and especially the fantastic crew.Hawaii hospitality is truly unmatched, and the Sail Maui crew is a perfect example of it. ❤️Thank you, Sail Maui, for giving me such a memorable experience. I would absolutely do this trip again and highly recommend it to anyone visiting Maui! 🌺🐢🐬
Read more
Best snorkeling experience we've had
New York City
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
seanpF4297KZ, Sep 2026
Best snorkeling experience we've had
Every part of the crew was absolutely amazing. We had an amazing experience and highly recommend. The crew was not only very sweet and caring, they were very attentive to everyone and their needs. We were fortunate to be able to see a monk seal and whale shark in a matter of 30 minutes which we heard was extremely rare. 10/10 would definitely come back
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
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
Highly recommend booking...
New York City
Day’s End Cocktail Sunset Sail
Alessandra_L, Sep 2026
Highly recommend booking...
Highly recommend booking - staff was kind and knowledgeable and the ocean views were truly amazing!!
Read more
Best captain and crew in Maui
New York City
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Ratherbeatthelake, Sep 2026
Best captain and crew in Maui
We LOVED our day on Ali’i Nui catamaran. The snorkel trip to Molokini Crater was fabulous. Could see for 100ft clear water. All of staff were super friendly and helpful. Loved having a female captain. Jordan was awesome as was all of her crew. Food and drinks were great. We will definitely book with them again when we are in Maui.
Read more
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