Oahu Cruises, Sailing & Water Tours

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Oahu Activities

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Waikiki Sunset Boat Cruise
Likely to Sell Out
Likely to Sell Out
5.0 (227)

Waikiki Sunset Boat Cruise

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (227)
from
$50
Ko Olina Glass Bottom Boat Tour - 1 Hour Reef Adventure
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Ko Olina Glass Bottom Boat Tour - 1 Hour Reef Adventure

Discover one of the top-rated ocean experiences in Ko Olina on this exciting 1-hour Glass Bottom Boat Reef Adventure along Oahu’s beautiful West Side. Departing...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (1)
from
$51
1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran
5.0 (80)

1-Hour Diamond Head Sail from Waikiki Beach on Ke Kai Catamaran

Join us for a 1-hour fun-filled sail departing directly off of Waikiki Beach! Enjoy a breezy midday diamond head sail with complimentary drinks on YELLOW...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (80)
from
$53
Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
4.7 (1,265)

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (1,265)
from
$53
Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value
4.9 (253)

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle,...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (253)
from
$53
Waikiki Beach Whale Watching: Catamaran Sail & Open Bar
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
Sunset Whale Watch in Waikiki, Whales Guaranteed or Free Return
Likely to Sell Out
Likely to Sell Out
4.9 (111)

Sunset Whale Watch in Waikiki, Whales Guaranteed or Free Return

Free return trip if no whales are sighted! Our beautiful double decker tour boat is the best platform for viewing whales! Experience Humpback Whales in...

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
4.9 (111)
from
$54
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
4.9 (983)

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

2025 Cool Hawaii TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (983)
from
$55
Bikini Bottom Public Party Dance Cruise + LIVE DJ
4.7 (79)

Bikini Bottom Public Party Dance Cruise + LIVE DJ

- LIVE DJs on board, amazing dance music and sound systems - Bar on Board with 2 Free Drinks - Sunny, warm weather and breathtaking...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (79)
from
$55
Oahu Whale Watching Catamaran Sail Experience
Likely to Sell Out
Likely to Sell Out
3.0 (1)

Oahu Whale Watching Catamaran Sail Experience

Join an intimate whale watching adventure aboard open-deck sailing catamaran, limited to just 35 guests for a more personal experience. Every winter, humpback whales migrate...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
3.0 (1)
from
$55
Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran
4.9 (164)

Board from Waikiki Beach for Aloha Hour Sail on Hāwea Catamaran

Step aboard Hawea, our hand-built 50′ catamaran, for a 90-minute afternoon sail that blends the laid-back spirit of Waikiki with the festive energy of happy...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (164)
from
$55
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure
4.8 (590)

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (590)
from
$56
Beautiful 90 Minute Catamaran Sunset Sail with Drinks!
4.9 (11)

Beautiful 90 Minute Catamaran Sunset Sail with Drinks!

The nightly Sunset Sailing trip is a gorgeous 90-minute sail with complimentary drinks. Experience sailing, sightseeing, delicious cocktails, the beautiful Hawaiian Sunset, and perhaps if...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (11)
from
$56
Magic Island Honolulu Stand Up Paddling
5.0 (26)

Magic Island Honolulu Stand Up Paddling

Join us for a morning paddle with Hawaiian sea turtles! This beginner class is perfect for anyone interested in trying standup paddling (SUP) for the...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (26)
from
$57
Waikiki: BYOB Sunset Cruise
4.9 (706)

Waikiki: BYOB Sunset Cruise

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on a boat out at sea....

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (706)
from
$59
Waikiki Friday Fireworks Boat Cruise from Oahu
4.6 (57)

Waikiki Friday Fireworks Boat Cruise from Oahu

Experience the iconic Waikiki fireworks like never before on our sunset sail aboard a 55-foot double-decker catamaran. With spacious decks and a underwater viewing room,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (57)
from
$59

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.

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

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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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