Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles
5.0 (3)

Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or...

8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
5.0 (3)
from
$1,200
Private Boat Charter North Shore Oahu
5.0 (6)

Private Boat Charter North Shore Oahu

Our North Shore adventure tours are perfect for people of all ages. Bring your family or friends and create new memories. Turn the tour into...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$1,200
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure
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
Private Luxury Sunset Cruise Aboard Limitless
Likely to Sell Out
Likely to Sell Out

Private Luxury Sunset Cruise Aboard Limitless

Set sail with on a private 2-hour sunset cruise, the perfect way to wind down your day in Hawaii. As the sun sinks toward the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
from
$1,199
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
Likely to Sell Out
Likely to Sell Out
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
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

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 Luxury Sunset Cruise in Waikiki

Private Luxury Sunset Cruise in Waikiki

Experience the ultimate luxury and exclusivity with a private yacht cruise in Waikiki, where you can bask in the breathtaking beauty of the Hawaiian sunset...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
from
$1,000
Private Catamaran Charter in Waikiki (1-6 Guests)
Likely to Sell Out
Likely to Sell Out
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
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
Oahu Private First, Last and Transfer Day Tours with Luggage
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Oahu Private First, Last and Transfer Day Tours with Luggage

Make the first or last day of your vacation the best one, without any hassle or wasted time.  We all know the feeling of an early...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (2)
from
$799
Private Catamaran Cruise and Snorkeling Tour in Honolulu
Likely to Sell Out
Likely to Sell Out
5.0 (152)

Private Catamaran Cruise and Snorkeling Tour in Honolulu

Discover the beautiful views of the ocean, local wildlife, and the iconic east side of Oahu as you join me on a private catamaran cruise...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (152)
from
$749
Private Snorkeling and Wildlife on The Adventure Boat
5.0 (88)

Private Snorkeling and Wildlife on The Adventure Boat

**Private boat tour for up to 6 people** Larger group? Call for options. Fast and fun adventure sightseeing tours in Hawaii. Escape the crowds and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (88)
from
$725
Private Sunset Catamaran Cruise in Waikiki
Likely to Sell Out
Likely to Sell Out
5.0 (70)

Private Sunset Catamaran Cruise in Waikiki

Discover the beautiful views of the ocean, local wildlife, the iconic east side of Oahu, and the sun dipping into the sea as you join...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (70)
from
$699
Uniquely Personalized Private Island Tour on Oahu, Hawaii
Likely to Sell Out
Likely to Sell Out
5.0 (46)

Uniquely Personalized Private Island Tour on Oahu, Hawaii

Plan Your Personalized Private Tours around any activity or event that you want.  You can even combine this option with other activities you find on...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (46)
from
$699
Oahu Custom Private Circle Island and Mini Circle Island Tours
Likely to Sell Out
Likely to Sell Out
5.0 (20)

Oahu Custom Private Circle Island and Mini Circle Island Tours

See all O`ahu has to offer and enjoy a ride around the Ko`olau Mountain Range.  Visit the South or North Shore on a Mini Circle...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (20)
from
$699

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.

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Gather your information

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

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

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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

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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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