Hawaii Sailing Trips

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Hawaii Activities

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3 Hour Luxury Private Sailing Catamaran for 7-12 People
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
3 hours • Free Cancellation
3 hours • Free Cancellation
from
$1,995
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (1)

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
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$1,595
2hr Luxury Private Sailing Catamaran for 7-12 People
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$1,495
Private Oahu Sunset Charter with Tasting and Drinks
Likely to Sell Out
Likely to Sell Out
Oahu, USA
5.0 (52)

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
120 to 150 minutes • Free Cancellation
120 to 150 minutes • Free Cancellation
5.0 (52)
from
$1,413.61
Luxury Diamond Head Sunset Sail
Oahu, USA
5.0 (3)

Luxury Diamond Head Sunset Sail

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$1,398
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (2)
from
$1,200
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure
Oahu, USA
5.0 (3)

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun....

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (3)
from
$1,199
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (14)
from
$1,150
Private South Shore Sail Charter
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
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (2)
from
$1,000
Private Morning Ceremony Sailing Charter
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
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
from
$1,000
Private Catamaran Charter in Waikiki (1-6 Guests)
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (25)
from
$900
Private Catamaran Sunset Sail in Waikiki
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (11)
from
$900
Diamond Head Sunset Sail
Oahu, USA
5.0 (14)

Diamond Head Sunset Sail

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (14)
from
$695
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
Oahu, USA
5.0 (3)

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (3)
from
$695
Private Whale Watching Sailing Adventure
Oahu, USA
3.5 (2)

Private Whale Watching Sailing Adventure

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
3.5 (2)
from
$695
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (4)
from
$450

Frequently Asked Questions

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

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Lowest Price Guarantee

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We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity starts.

We Make It Easy!

Gather your information

Locate your Cool Hawaii Booking Number and the proof of the lower price you found.

Send it to us

Email [email protected] with the documents, your name, and your home address.

We'll review

We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Hawaii promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same activity, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Hawaii and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased activity into one or more parts sold separately.
  • Cool Hawaii reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Hawaii.

Sorting, ranking, and search results

Activity name

Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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