Hawaii Sailing Trips

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Hawaii Activities

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3 Hour Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

3 Hour Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours • Free Cancellation
from
$1,995
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (2)

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

3 hours • Free Cancellation
5.0 (2)
from
$1,595
2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (3)

2hr Luxury Private Sailing Catamaran for 7-12 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours • Free Cancellation
5.0 (3)
from
$1,495
Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (55)

Private Oahu Sunset Charter with Tasting and Drinks

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people...

120 to 150 minutes • Free Cancellation
5.0 (55)
from
$1,414
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (2)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6...

2 hours • Free Cancellation
5.0 (2)
from
$1,200
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (14)

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and...

2 hours • Free Cancellation
4.8 (14)
from
$1,150
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
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
#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
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
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
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
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
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

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
Amazing
New York City
Private Oahu Sunset Charter with Tasting and Drinks
Guide28106223149, Sep 2026
Amazing
I can’t thank Mana Cruises enough for their amazing hospitality! Ella graciously greeted us. Captain Travis and Leah made each guest feel welcomed and safe! This is not my first time with them and certainly not the last! Mahalo Mana Cruises for making our Sunset cruise so special!!!
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
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
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
Exceptional experience.
New York City
Private Oahu Sunset Charter with Tasting and Drinks
V2985KBvictora, Aug 2026
Exceptional experience.
We booked a private tour with Mana Cruises, and it was truly an unforgettable experience! My son proposed during the cruise, and the crew went above and beyond with their incredible hospitality to make the moment extra special. Watching the sunset right after was pure magic. We couldn't have asked for a better evening or a more attentive crew!"The sunset was breathtaking, and the memories will last a lifetime. Highly recommend!"
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
Awesome experience
New York City
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Climber19817325401, Aug 2026
Awesome experience
The crew took excellent care of us. The small and private experience provided a more intimate setting, allowing for more personalized attention. We had the opportunity to see dolphins and even go snorkeling. The experience was highly customizable, making it an ideal choice for those seeking a private and memorable adventure.
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
Unreal experience
New York City
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
Emma_I, Jul 2026
Unreal experience
It was so much fun!! Amazing crew and we saw beautiful wildlife!! So crazy to see turtles and fish up close. We were also able to jump off the boat into the ocean. Unreal experience! 10/10
Read more
Better than advertised!
New York City
Private Catamaran Charter in Waikiki (1-6 Guests)
derickg967, Jul 2026
Better than advertised!
Captain Steve and Bella were amazing! They made the trip so enjoyable and were so easy going. I would highly recommend you book with them now!
Read more
Best experience in the sea
New York City
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
E2422ZTveronicad, Jun 2026
Best experience in the sea
So customized. Great experience. Captain and crew were perfect in the sense that the did theor job and we had quality family time. Pitty we could not snorkel due to climate. But we sailed woth music. Unforgetable
Read more
A wonderful 3 hours with family on the water at Waikiki
New York City
Private Catamaran Sunset Sail in Waikiki
Burleya13, May 2026
A wonderful 3 hours with family on the water at Waikiki
A great day on the water with Tom, Savannah and Bella celebrating Alicia’s 70th birthday with our children and grandchildren. Swimming off the catamaran with dolphins and turtles. We also saw a seal in the harbour before sailing. A great birthday present and memories. Highly recommend the professional expertise of the crew.
Read more
Great Sailing Trip
New York City
Private Catamaran Charter in Waikiki (1-6 Guests)
Dave1151a, May 2026
Great Sailing Trip
My entire family had a fantastic experience. Captain Tom , Savanah, Hailey were great hosts. We went to a quiet swim/snorkeling area. Saw plenty of fish. A very peaceful tranquil outing.
Read more
Captain Sam!!!!
New York City
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
derrickr463, Apr 2026
Captain Sam!!!!
Captain Sam and Shelby were incredible!!!!! Extremely fun and accommodating and made our trip beyond special! Lifelong memory made!
Read more
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