Hawaii Sailing Trips

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Hawaii Activities

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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
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
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
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
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
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
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (19)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

2 hours • Free Cancellation
4.8 (19)
from
$279
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step …More

Likely to Sell Out
Likely to Sell Out
Maui, USA
4.8 (61)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes • Free Cancellation
4.8 (61)
from
$289
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
Kauai’s Na Pali Coast Snorkel and Sail Tour

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making …More

Likely to Sell Out
Likely to Sell Out
Kauai, USA
4.9 (558)

Kauai’s Na Pali Coast Snorkel and Sail Tour

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making...

6 hours • Free Cancellation
4.9 (558)
from
$292
Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (17)

Waikiki private Day Tour and Sunset sail for couples

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples...

2 hours • Free Cancellation
5.0 (17)
from
$300
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed …More

Oahu, USA
5.0 (4)

#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed...

2 hours • Free Cancellation
5.0 (4)
from
$450
Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (25)

Private Catamaran Charter in Waikiki (1-6 Guests)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on...

2 hours • Free Cancellation
5.0 (25)
from
$900
Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (11)

Private Catamaran Sunset Sail in Waikiki

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which...

2 hours • Free Cancellation
5.0 (11)
from
$900
Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, …More

Oahu, USA
5.0 (2)

Private South Shore Sail Charter

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze,...

1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$1,000
Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

Private Morning Ceremony Sailing Charter

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to...

1 hour 30 minutes • Free Cancellation
from
$1,000

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
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
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
Honeymoon cruise
New York City
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
camirenR, Sep 2026
Honeymoon cruise
Exceeded our expectations the food and drinks were amazing. Brandon and the rest of the crew aboard were excellent and got anything you needed right away. A little spendy but 100% worth the experience!!!
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
Sunset boat ride
New York City
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
robertbE1580JV, Sep 2026
Sunset boat ride
Excellent experience worth the price. Captain Spence and Logan took care of us. A highlight of our trip. A relaxing boat ride with a fun ride back to the pier. 10 out of 10!!
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
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
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
My experience was great...
New York City
Kauai’s Na Pali Coast Snorkel and Sail Tour
Pierre_H, Aug 2026
My experience was great...
My experience was great except that Cool Hawaii did not give all the informations that was necessarily for me to move forward or not with my booking. It happen that my 4 years old could not go bcs he was under 5. That was a birthday trip and Cool Hawaii ruin the experience bcs of the lack of information this not the first of happen but it won’t happen again bcs I want use Cool Hawaii again
Read more
Great trip
New York City
Polynesian Canoe Sunset Sail
jfpetesn, Aug 2026
Great trip
Had a wonderful time. Great experience
Read more
Windblown and laughing
New York City
Kauai’s Na Pali Coast Snorkel and Sail Tour
Scenic473469, Aug 2026
Windblown and laughing
Amazing staff…heads in a swivel at all times. Captain was professional yet warm and personal. Had a wonderful time, had the ability to sit anywhere on the catamaran..wind, waves and incredible vistas. Had pods of dolphins travel with us.
Read more
Great yacht and captain
New York City
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Gleb_K, Aug 2026
Great yacht and captain
Was great! Yacht was clean and comfortable. Captain was super friendly and nice. Weather and view as usual - great.
Read more
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