Hawaii Sailing Trips

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Hawaii Activities

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Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, …More

Big Island of Hawaii, USA
5.0 (6)

Afternoon Ali'i Adventure

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests,...

3 hours • Free Cancellation
5.0 (6)
from
$276
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
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
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, …More

Oahu, USA
4.8 (35)

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May,...

2 hours • Free Cancellation
4.8 (35)
from
$250
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
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
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in …More

Maui, USA
4.8 (830)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours • Free Cancellation
4.8 (830)
from
$213
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
5.0 (33)

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours • Free Cancellation
5.0 (33)
from
$203
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

Maui, USA
4.9 (218)

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours • Free Cancellation
4.9 (218)
from
$200
Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (28)

Polynesian Canoe Day Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
5.0 (28)
from
$200
Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the …More

Oahu, USA
5.0 (18)

Polynesian Canoe Morning Sail

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the...

2 hours • Free Cancellation
5.0 (18)
from
$200
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
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above …More

Honolulu, USA
4.7 (67)

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (67)
from
$197
Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, …More

Likely to Sell Out
Likely to Sell Out
Lahaina, USA
5.0 (49)

Snorkel Sail Adventure off Ka'anapali Beach in Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

4 hours • Free Cancellation
5.0 (49)
from
$193
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

Likely to Sell Out
Likely to Sell Out
Big Island of Hawaii, USA
5.0 (711)

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 (711)
from
$189
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

Frequently Asked Questions

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

Recent activity reviews
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
Experience that lives up to the hype + plused by the crew
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jason_H, Sep 2026
Experience that lives up to the hype + plused by the crew
Great for families with small kids. Not overbooked, great boat and accommodations, multiple ways for young kids to engage in the experience - life vests, floating vessels, placards to pinpoint wildlife, etc. crew was very engaging, personable, and caters to our family needs. Even let the kids "drive" the boat. Couldn't recommend more.
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
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
Turtle snorkeling
New York City
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
martinnN4650NC, Sep 2026
Turtle snorkeling
Wonderful experience we saw a bunch of turtle.
Read more
Great snorkeling on Maui!
New York City
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Marisa_F, Sep 2026
Great snorkeling on Maui!
Wonderful snorkeling trip with a great crew. Lunch was delicious. We saw a lot of turtles. The boat is beautifully maintained.
Read more
Great experience!
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jeanine_D, Sep 2026
Great experience!
Crew was fantastic! Friendly and experienced helping guests that need support! Recommend this company!
Read more
Amazing service
New York City
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
Tatiana_J, Sep 2026
Amazing service
Captain Patrick and his crew were amazing, friendly, knowledgeable and helpful. Weather was perfect, drinks cold , ocean water was great.
Read more
Breathtaking and so much fun
New York City
Kauai: Leila Na Pali Sunset Dinner Sail
996carleens, Sep 2026
Breathtaking and so much fun
Probably the best day here on Kauai. We had originally booked the snorkel tour but due to the hurricane they cancelled that. When I called, they were so accommodating and suggested the sunset cruise the same day. Honestly so much fun, crew was amazing, food delicious and I can’t say enough! And the playlist made by the captain himself was perfect. Thank u for being the highlight of our vacation. Would highly recommend. Thank u guys!
Read more
Beautiful but bouncy.
New York City
Kauai: Leila Na Pali Sunset Dinner Sail
Normina_v, Sep 2026
Beautiful but bouncy.
Crew was amazing, food was tasty. We saw dolphins and beautiful cliffsides. It is a very long tour and even I was a little seasick from being bounced around for 4 hours by the end.
Read more
Informative and stunning sunset sail
New York City
Polynesian Canoe Sunset Sail
H4936RZvictoriak, Sep 2026
Informative and stunning sunset sail
My husband and I came to Hawaii for our anniversary trip. We had one day in Honolulu and we wanted to take this sunset cruise. It was so informative and well done. Our guides, Nani and Jaslyn, were so knowledgeable and friendly. They taught us a little Hawaiian, how to make poi, how to make a lei, and were so excited to answer any questions we had. The rest of the crew was super kind and we got to try some more traditional foods. Even when my husband and I both got seasick from how choppy the waves were, the crew took care of us and were nothing but kind. If you’re looking for a truly unique cultural experience, don’t pass this by!
Read more
Best sunset cruise ever!!!
New York City
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
mickiherg, Sep 2026
Best sunset cruise ever!!!
It can be rough seas..5 to 6 people got seasick.. Word to the wise..The taco bar was terrific lots of food and plenty of booze.. Except..they did run out of chardonnay. Not good.. Captain and crew were the best EVER!!!
Read more
Amazing cruise and sunset!
New York City
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Greg_B, Sep 2026
Amazing cruise and sunset!
Captain Evan and his crew made for an amazing day! Evan was very informative and knowledgeable about the island and his crew went above and beyond with serving us food and drinks! My family had a blast!
Read more
Sail & Snorkel aboard The Gemini
New York City
Snorkel Sail Adventure off Ka’anapali Beach in Maui
534AnneS534, Aug 2026
Sail & Snorkel aboard The Gemini
We had an awesome experience aboard the Gemini. We met the tour guide by the Westin, then walked together to the other side of Black Rock, where we boarded the catamaran from the beach. The surf was apparently too rough to board by the Westin that day. The boat seemed to have the right amount of people aboard, so it did not feel packed. You could easily move about the boat with plenty of room.It took us to the West Maui snorkel spot, Honolua Bay. The water was clear and fish were plentiful. We even saw a turtle! Lunch and drinks were served on the boat after snorkeling. The crew was great, and really helped ensure we all had fun. I would highly recommend the tour.
Read more
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