Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Diamond Head Sunset Sail
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
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
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
Likely to Sell Out
Likely to Sell Out
5.0 (13)

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (13)
from
$53.36
Sunset Cruise along Waikiki Coastline
5.0 (12)

Sunset Cruise along Waikiki Coastline

Embark on an unforgettable journey aboard our intimate sunset cruise, where the Hawaiian sky transforms into a stunning canvas of gold, pink, and violet hues....

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (12)
from
$124
Private Whale Watching Activity: 6 passengers max
Likely to Sell Out
Likely to Sell Out
5.0 (11)

Private Whale Watching Activity: 6 passengers max

Our Captain and mates have travelled all over the polynesian islands to experience other whale-watching tours and have used all the information we've learned from...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (11)
from
$523.56
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
Waikiki Friday Fireworks Party Cruise with Live DJ & Full Bar
5.0 (10)

Waikiki Friday Fireworks Party Cruise with Live DJ & Full Bar

Experience the ultimate Waikiki Friday night party cruise - complete with front-row views of the famous Waikiki Fireworks show! This 21+ Only party cruise includes...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (10)
from
$99
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
5.0 (10)

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon...

4 hours • Hotel pickup offered • Free Cancellation
4 hours • Hotel pickup offered • Free Cancellation
4 hours • Hotel pickup offered • Free Cancellation
5.0 (10)
from
$120
Self-Guided Kayaking Tour in Kailua Bay and Popoia Island
5.0 (9)

Self-Guided Kayaking Tour in Kailua Bay and Popoia Island

Meet in Kailua at the Active Oahu storefront where friendly staff will help you load your kayaks and gear. From there drive a few minutes...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (9)
from
$82
Oahu Personalized Private North Shore Highlight Custom Tour
Likely to Sell Out
Likely to Sell Out
5.0 (7)

Oahu Personalized Private North Shore Highlight Custom Tour

Explore the Seven Mile Miracle known as O`ahuʻs North Shore.  Winter brings big waves and world-class surfing, while the summer is calm and perfect for visiting...

6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (7)
from
$699
Guided E-Bike and Kayak Tour to Mokulua Islands in Kailua, Oahu
5.0 (7)

Guided E-Bike and Kayak Tour to Mokulua Islands in Kailua, Oahu

Embark on an exhilarating 5-hour journey to the Mokulua Islands, led by our experienced guides! Say goodbye to car hassles—your transportation to Kailua Beach is...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (7)
from
$285
Waikiki Beach Catamaran Friday Night Fireworks Tour
5.0 (7)

Waikiki Beach Catamaran Friday Night Fireworks Tour

This sail only happens once a week and there’s no better way to take in the fireworks than from the waters aboard our catamaran, where...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (7)
from
$71
Guided Kayak Tour to Kailua’s Twin Islands
5.0 (6)

Guided Kayak Tour to Kailua’s Twin Islands

Embark on an exhilarating guided kayak tour to the Mokulua Islands, led by our experienced guides! As we paddle towards Moku Nui, a designated bird...

3 to 5 hours • Free Cancellation
3 to 5 hours • Free Cancellation
3 to 5 hours • Free Cancellation
5.0 (6)
from
$219
Private Boat Charter in Waikiki for Snorkeling and Events
Likely to Sell Out
Likely to Sell Out
5.0 (6)

Private Boat Charter in Waikiki for Snorkeling and Events

Discover the beauty of Waikiki with a private boat day charter, perfect for snorkeling, coastal cruising, events, and seasonal whale watching from January to March....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (6)
from
$1,300
Sunset Sail Experience by Catamaran in Waikiki
4.8 (6)

Sunset Sail Experience by Catamaran in Waikiki

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (6)
from
$92.31
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

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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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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