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Sailing Charters on Oahu

There are 28 products in this category that range in price from $29.90 to $1215.90.


Oahu sailing charters can bring a gentle breeze into your Hawaiian vacation or an Oahu sailing trade wind adventure.



Let's get down to sailing basics. Oahu is an island that is surrounded by water and by wind. Sail boats are designed to catch the wind and sail on the water. There are lots of Oahu sailing vessels on all coasts of the island. All this equals a great sailing experience available for you and your family on one of Oahu's many sailing tours, sailing lessons or sailing charters.

As with all the Hawaiian Islands, Oahu is blessed, about 300 days of the year, with the prevailing "trade winds". These winds generally blow from out of the north-east and vary from 5 to perhaps 25 miles per hour which are excellent conditions for Oahu sailing charters. Mornings on Oahu are generally calm or have gentle winds suitable for light sailing but as the day progresses the trade winds usually become stronger and a stiff wind can become a consistent force for Oahu sailing vessels by mid afternoon. In the evenings and at sunset time the winds will usually die down again and return to a gentle breeze. This is probably an over exaggeration of the usual Oahu sailing day but it generally meets the overall daily template as it relates to sailing Oahu's coasts.

Where do Oahu sailing charters sail?
  • Kewalo Basin is by far the most departed from harbor for all Oahu sailing charters. The harbor is located in Honolulu just a stone's throw from Waikiki and most of your Oahu sailing charters will pick you up right from your Waikiki hotel and bring you to the departure point. The oceans off Honolulu and Waikiki are generally somewhat protected from wind by the mountains behind but can provide an excellent sailing experience particularly in the afternoon hours.

  • Oahu's North Shore off the coast line of Haleiwa is also a starting point for Oahu sailing charters and this coastline can often provide an even stiffer wind for your Oahu sailing adventure because of its less protected positioning on the island and can be in a direct line to the prevailing trades as they wrap around the island. Keep in mind however that the winter time can bring with it giant surf on this coastline and can sometimes alter, interrupt or even cancel your Oahu sailing adventure for the day.



Types of Oahu sailing boats
  • Many of the Oahu sailing vessels are catamarans and they vary in size and capacity greatly. Sailboat charter lengths can vary from 35' to 65' and capacities on these sailing catamarans can vary from a maximum of 20 passengers to a maximum of 80 passengers.

  • Charter sailing yachts can be very exclusive, carrying only 6 passengers and have amenities that can rival a penthouse condo.


We sell tickets to 28 items in the category Sailing Charters on Oahu.

View the complete list below or use our Activity Finder to narrow down your options.

Displaying 28 of 28 Results

$44.90
(4 Reviews, 5 Stars)

Sail out to Waikiki's best diving spots, where you can swim, snorkel and explore the reef. Afterwards, have lunch aboard the boat, then kick back, listen to tunes, soak up the sun and enjoy an exhilarating…

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$79.00
(3 Reviews, 5 Stars)

There's nothing like a Hawaiian sunset, and nothing beats seeing a sunset from sea. During this trip you will enjoy a scenic cruise from the Hilton Pier south towards Diamond Head. Normally the captain…

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$88.90
(3 Reviews, 5 Stars)

Set sail for an adventure aboard the sleek Ho'o Nanea and snorkel in the clear tropical water near famous Waimea Bay. Our expert crew will show you tropical fish and fascinating reef formations. A…

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$94.90
(3 Reviews, 5 Stars)

From Waikiki, your professional nature guide will shuttle you by van to a tropical rain forest past Puowaina (Punchbowl Crater) to the top of Pu'u Ohia (Tantalus), where you'll be outfitted with…

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$71.90
(3 Reviews, 5 Stars)

The North Shore of Oahu has more whale sightings than any other location on Oahu. Last season there were over 700 sightings and two double breaches in the Haleiwa Harbor Channel. Between December and…

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$99.00
(2 Reviews, 5 Stars)

Enjoy an all-you-can-eat lunch at sea, and snorkel in Hawaii's beautiful azure waters at the Turtle Canyon. Our eco-conscious cruise lets you see whales (in season, late November through April), fish,…

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$55.90
(2 Reviews, 5 Stars)

Cruise along the picturesque North Shore to the Waimea Bay area. Feel free to bring your own alcoholic beverages.

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$704.90
(1 Review, 5 Stars)

This sail is perfect for visitors with a desire for real sailing in a private setting. Departure from Honolulu permits guests to enjoy the beauty and excitement of blue water sailing year round, while…

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$51.90
(1 Review, 5 Stars)

This snorkel tour is ideal for those on vacation that want a later start to their day. Snorkeling in Hawaii is very fun and easy. If you've never snorkeled before, no worries, it is not difficult!! We…

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$91.91
(3 Reviews, 4.7 Stars)

Sail out to Turtle Canyon along the south shores of Honolulu and Waikiki and snorkel off the boat in the warm water where you will see turtles and a variety of fish. On your trip back, keep an eye open…

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$468.90 - $1215.90

Your loved one's ashes can be scattered on the smooth ocean waters of Hawai'i by your family and friends or by the captain, during a beautiful sunrise or sunset. Pay your last respects to a loved…

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$570.90 - $1133.90

Individuals, families and small groups or companies can sport fish in privacy aboard our comfortable vessel. A variety of reef fish are caught while anchoring or drift fishing over reefs on a reef fishing…

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$468.90 - $704.90

Between December and May every year, humpback whales visit the Hawaiian Islands. These whales reach lengths of 35 to 50 feet and weigh up to 50 tons. These intelligent visitors return annually to deliver…

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$468.90

This sail is ideal for the romantic couple who is up at dawn due to time zone changes. Enjoy the brilliant colors of a sunrise at sea from the deck of the Love Boat. Enjoy complimentary mimosas (champagne…

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$468.90

Develop your basic skills and knowledge to further your sailing dreams. Through private lessons and hands-on instruction, sailors quickly advance, developing the confidence and competence to safely operate…

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$159.90

The 3 hour adventure begins with thorough instruction by our certified guides at He'eia State Park. Journey to Kaneohe Bay which is protected by Oahu's only Barrier Reef. Sailing sites are weather…

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$135.00

Set sail from Waikiki Beach onboard the 54 foot catamaran Spirit of Aloha to view the fireworks and eat dinner at sea. During the cruise you will be served an array of gourmet, fresh selections. The menu…

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$174.90

The destination of this trip is usually at Turtle Canyon where you can snorkel in 20 feet of water for 35 to 45 minutes over beautiful tropical reefs filled with many varieties of fish and sea creatures.…

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$131.90

Board the Island Princess, a sturdy catamaran, and begin to cruise Oahu's Waianae coastline to search for and swim with dolphins. We will perform chanting for safety in the traditional Hawaiian style.…

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$64.06

Enjoy a nice 2 hour afternoon sail along the south shore and see the beautiful views of the lush Ko'olau Mountains, Diamond Head, Waikiki and Honolulu sky lines. Spinner Dolphins are often seen and…

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$79.00

See the scenic Ko Olina Coast, which usually includes at least one dolphin sighting. Cruise and snorkel, or upgrade to the stand up paddle board package. During whale watching season from December through…

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$139.90

From Waikiki, your professional nature guide will shuttle you by van to their own private 75 acre property in Manoa Valley. You'll be issued trail snacks and a water bottle with optional rubber boots…

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$49.00

Set sail on an expedition to Diamond Head. Along the way you'll have the opportunity to take in the sights and delights of Oahu's beautiful natural and city scenery. See marine wildlife in their…

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$56.90 - $63.90

Sunset, stargazing and full moon cruise. These trips are usually available two nights out of each month, most of the year. Tour is run in lieu of the traditional sunset cruise. Dates are determined by…

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$51.90

Go snorkeling on the newest boat in the Hawaiian Islands. Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities on this…

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$32.47

The trade-winds provide the backdrop as Maita`i surfs the swells off Waikiki. The wind and waves rush by on this unique hour and a half sail.

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$51.90

Meet at Kewalo Basin to board a 38 foot catamaran. Relax and unwind as you sail off the coast of Waikiki and Le'ahi (Diamond Head). Weather permitting, there will be optional swimming and snorkeling.…

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$29.90

Come and experience an afternoon tradewind sail on the newest boat in the Hawaiian Islands. Enjoy a fun and high speed sailing adventure along Oahu's beautiful coastline with incredible views of Waikiki…

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