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Discount Hawaii Activities & Things to do



Oahu Sailing

Go sailing during your vacation on Oahu. Much more intimate than a standard dinner cruise, sailing gives you the chance to be closer to the water's surface and enjoy a fun glide across the azure blue Hawaiian waters.

Hawaii Discount offers several popular Oahu sailing tours at discounted rates. Come aboard the Makani Nui or Maitai Catamaran or enjoy a sailing adventure on Oahu's North Shore. From families or couples to singles and groups of friends, Oahu sailing tours are for everyone. Find great deals on Oahu's best sailing tours on Hawaii Discount.

Popular Oahu Sailing Tours

SAVE UP TO 5%
Maita'i Catamaran - Tradewinds Sail
Hop on board the Maita'i, a state-of-the-art catamaran for a fun sail along the Waikiki coastline.
DURATION: 1.5 HOURS
from $45.00
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SAVE UP TO 10%
Maita'i Catamaran - Afternoon Delite Sail
Set sail from Waikiki Beach and enjoy beautiful coastline views of Oahu's south shore, as well as our "delite"ful friends that we often encounter, such as dolphins, turtles, flying fish and whales (seasonal) to name a few.
DURATION: 1.5 HOURS
from $69.00
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SAVE UP TO 10%
Maita'i Catamaran - Sunset Mai Tai Sail
Sit back and enjoy Hawaii's beauty as you experience a Hawaiian sunset. Complimentary beverages include Mai Tais, beer, wine, champagne, juices and soft drinks.
DURATION: 1.5 HOURS
from $69.00
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SAVE UP TO 15%
Makani Catamaran - Fun in the Sun Sail
Enjoy an afternoon sail off Waikiki Beach. Relax in the Makani Catamaran's semi-enclosed cabin or lie down on the sunbathing net and enjoy the sun.
DURATION: 2 HOURS
from $115.00
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SAVE UP TO 6%
Port Waikiki Cruises - Waikiki Adventure Sail
Come aboard the Spirit of Aloha and enjoy a sailing adventure along the Waikiki coastline. Sail toward Diamond Head and enjoy the sights of Oahu’s scenic south shore along the way.
DURATION: 1 HOUR
from $42.50
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SAVE UP TO 15%
Makani Catamaran - Friday Night Fireworks Sail
Enjoy a unique vantage point of the Friday night fireworks in Waikiki. Come aboard the Makani Catamaran for an evening sail along Waikiki Beach. An island-style dinner and a drink is included!
DURATION: 1 HOUR
from $75.00
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SAVE UP TO 8%
Hawaii Nautical - Waikiki Sunset Cocktail Sail
Enjoy a romantic sunset sail along the Waikiki shoreline. There is nothing like a Hawaiian sunset, and nothing beats watching one at sea. This scenic sunset sail takes you south toward Diamond Head.
DURATION: 1.5 HOURS
from $92.00
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SAVE UP TO: 10%
Port Waikiki Cruises - Sunset Cocktail Cruise (Hilton Pier - Waikiki)
Come aboard with Port Waikiki Cruises on this relaxing sunset cocktail cruise. This is a barefoot sailing excursion where you will enjoy the views of the ocean, sunset, and enjoy appetizers, snacks, and assorted beverages.
DURATION: 1.5 HOURS
from $132.00
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SAVE UP TO 5%
North Shore Catamaran - Sunset Sail
Enjoy a sail along Oahu's North Shore aboard the Ho'o Nanea. Relax in the warm evening sun and watch the spectacular scenery as the sun sets.
DURATION: 2 HOURS
from $69.00
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Ocean and You - Waikiki Sunset Cruise with Live DJ
Come aboard our all-new 2020 luxury powerboat for a sunset cruise along the Waikiki coastline. Take in the beautiful city views from the ocean and the glow of Diamond Head at the golden hour.
DURATION: 2 HOURS
from $79.00
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SAVE UP TO 15%
Makani Catamaran - Sunset Sail
View the setting sun from the Makani Catamaran in Waikiki. Sit back and relax on this fun Oahu south shore sail.
DURATION: 2 HOURS
from $115.00
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SAVE UP TO 10%
Maita'i Catamaran - Fireworks Sail
Enjoy a sail along Waikiki Beach after sunset, just in time for the weekly Aloha Friday fireworks show. Great photo opportunities!
DURATION: 1.5 HOURS
from $69.00
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SAVE UP TO 15%
Hawaii Nautical - Waikiki Panorama Sail
Come aboard the Honu Lani, a beautiful 65-foot sailing catamaran, and enjoy a scenic cruise along the Waikiki coastline. Departing from Kewalo Basin Harbor, just 5-10 minutes from Waikiki, you’ll also get to see the Ala Moana shoreline with its scenic beach park as well.
DURATION: 1.5 HOURS
from $69.00
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SAVE UP TO 5%
Go Hawaii Watersports - Waikiki Fireworks Cruise
Set sail for an unforgettable evening aboard our 2-hour sunset cruise! Enjoy stunning views of Waikiki Beach as the sun sets on the horizon, followed by a dazzling firework display that lights up the night sky.
DURATION: 2 HOURS
from $75.00
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