Oahu Cruises, Sailing & Water Tours

Custom Private Multi Day Tours on the island of Oahu Hawaii
Likely to Sell Out
Likely to Sell Out

Your Multi-Day Tours make sure you have the most fun possible, see everything you want, as well as have a driver for things like dinner, golf,...

3 daysHotel pickup offered
3 daysHotel pickup offered
3 days • Hotel pickup offered
5.0 (5)
from
$1,997.50

Oahu Personalized Private North Shore Highlight Custom Tour
Likely to Sell Out
Likely to Sell Out

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 hoursHotel pickup offered
6 to 12 hoursHotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (7)
from
$699

Waikiki to Diamondhead: Sunset BYOB Cruise
Likely to Sell Out
Likely to Sell Out

Want a spectacular sunset cruise? Our cruise offers multi level viewing of the dramatic Waikiki coastline and spectacular sunset on the water views. We offer...

2 to 190 minutesFree Cancellation
2 to 190 minutesFree Cancellation
2 to 190 minutes • Free Cancellation
5.0 (2)
from
$138.95

Offshore Fishing Adventures With Ohana Deep Sea Fishing
Likely to Sell Out
Likely to Sell Out

-Welcome aboard our well-equipped fishing charter boat and set off into the open seas with our expert captain and crew. - Explore prime fishing spots...

4 hoursFree Cancellation
4 hoursFree Cancellation
4 hours • Free Cancellation
5.0 (1)
from
$1,360

Oahu Customizable Private Community Service Voluntourism Offer
Likely to Sell Out
Likely to Sell Out

Want to give something back to Hawai`i?  So do we!  We will each donate 1.5 hours of any tour on the cause of your choice,...

6 to 12 hoursHotel pickup offered
6 to 12 hoursHotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (4)
from
$549

Oahu Private First, Last and Transfer Day Tours with Luggage
Likely to Sell Out
Likely to Sell Out

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 hoursHotel pickup offered
6 to 12 hoursHotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (2)
from
$799

Friday Night Waikiki Fireworks Cruise
Likely to Sell Out
Likely to Sell Out

Set sail for an unforgettable evening on our Waikiki Fireworks Cruise! Every Friday night, join us for a scenic cruise that takes you out into...

1 to 2 hoursFree Cancellation
1 to 2 hoursFree Cancellation
1 to 2 hours • Free Cancellation
4.1 (11)
from
$79

Private Waikiki Sunset Boat Tour: 6 passengers max

Experience the Magic of Waikiki: Sunset Boat Tour Join us for an unforgettable sunset boat tour in beautiful Waikiki, Oahu! As the sun dips below...

1 hour 30 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (19)
from
$314.14

Certified Diver 2 Tank Shallow Reef Dives Off Wai'anae
Likely to Sell Out
Likely to Sell Out

The best reef diving experience in Hawaiian waters! Join us on a guided tour of two beautiful reefs on the west shore of Oahu. As...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
5.0 (3)
from
$141.10

Personalized Private Pearl Harbor National Memorial Oahu Tours
Likely to Sell Out
Likely to Sell Out

Visit the World War II Valor in the Pacific National Monument at Pearl Harbor to reflect, remember and understand the tragic events of December 7,...

6 to 12 hoursHotel pickup offered
6 to 12 hoursHotel pickup offered
6 to 12 hours • Hotel pickup offered
5.0 (2)
from
$699

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 minutesFree Cancellation
1 hour 30 minutesFree Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (12)
from
$124

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (10)
from
$99

2hr Luxury Private Sailing Catamaran for 7-12 People
Likely to Sell Out
Likely to Sell Out

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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$1,495

Private and Luxurious Sunset Cruise with Dolphin Watch

Departing from Ko Olina Marina, this private sunset charter is reserved entirely for your group of up to 25 guests to experience the absolute best...

2 hours 30 minutesFree Cancellation
2 hours 30 minutesFree Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (5)
from
$2,875

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
Likely to Sell Out
Likely to Sell Out

(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 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (1)
from
$1,200

Moana’s Luxury semi-private Sunset Cruise on Nalu

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback...

2 hoursFree Cancellation
2 hoursFree Cancellation
2 hours • Free Cancellation
5.0 (17)
from
$149.99

Frequently Asked Questions

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

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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.