Oahu Cruises, Sailing & Water Tours

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Oahu Activities

Attractions

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Beautiful 90 Minute Catamaran Sunset Sail with Drinks!
5.0 (2)

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
5.0 (2)
from
$56.36
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
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
Private Whale Watching Sailing Adventure
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
Battleships of WWII at Pearl Harbor from Maui
5.0 (1)

Battleships of WWII at Pearl Harbor from Maui

Join us on a powerful historic journey starting with the surprise Japanese attack on Pearl Harbor December 7, 1941 that catapulted the U.S. into World...

7 to 9 hours • Free Cancellation
7 to 9 hours • Free Cancellation
7 to 9 hours • Free Cancellation
5.0 (1)
from
$459.99
Whale and Dolphin Watch Boat Cruise in Oahu
5.0 (1)

Whale and Dolphin Watch Boat Cruise in Oahu

Experience this sensational opportunity aboard our semi-private charter. We have limited our tours to just 6 guest per excursion to offer the most personalized adventure....

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (1)
from
$125
Affordable Afternoon Sail in Waikiki
3.7 (3)

Affordable Afternoon Sail in Waikiki

Looking for an unforgettable experience that won’t break the bank? Join us aboard Island Magic for the Aloha Hour a scenic, one hour sail offering...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
3.7 (3)
from
$30
Oahu: Ko Olina Kaula Kai Sunset Sail and Luau Experience
Likely to Sell Out
Likely to Sell Out
3.0 (1)

Oahu: Ko Olina Kaula Kai Sunset Sail and Luau Experience

Set sail on the stunning leeward coast of Oʻahu during the Kaula Kai experience, combining a breathtaking sunset sail with a vibrant luau. Start your...

90 to 180 minutes • Free Cancellation
90 to 180 minutes • Free Cancellation
90 to 180 minutes • Free Cancellation
3.0 (1)
from
$139
Private Cruise Swim with Dolphin
Likely to Sell Out
Likely to Sell Out

Private Cruise Swim with Dolphin

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild...

3 hours • Hotel pickup offered
3 hours • Hotel pickup offered
3 hours • Hotel pickup offered
from
$3,900.52
3 Hour Luxury Private Sailing Catamaran for 7-12 People
Likely to Sell Out
Likely to Sell Out

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
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
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 Snorkeling Cruise in Waikiki

Private Snorkeling Cruise in Waikiki

Embark on an unforgettable adventure with your very own private snorkeling tour to the legendary Turtle Canyon in beautiful Waikiki! Picture yourself diving into the...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
from
$1,560
Ko Olina Catamaran Snorkel and Luau Experience

Ko Olina Catamaran Snorkel and Luau Experience

Your adventure begins aboard the luxury catamaran Ko Nau Lani for a guided snorkel sail along Oʻahu’s stunning leeward coastline. Explore vibrant reef waters with...

2 to 6 hours • Free Cancellation
2 to 6 hours • Free Cancellation
2 to 6 hours • Free Cancellation
from
$149
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 Luxury Sunset Fireworks Cruise Aboard Limitless

Private Luxury Sunset Fireworks Cruise Aboard Limitless

Take your evening on the water to the next level with a private 3-hour Sunset + Fireworks Cruise. This trip combines the serene beauty of...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
from
$1,299
Friday Night Waikiki Fireworks Sail

Friday Night Waikiki Fireworks Sail

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
from
$699

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  • 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).
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  • 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.
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  • All refund decisions will be made at the sole discretion of Cool Hawaii.

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