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Hawaii Sailing Charters

Oahu offers an abundance of sailing charters.

There are 31 tours in this category with adult prices that range in price from $29.90 to $4500.00 Skip Directly to Tours.

Oahu Sailing Charters

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 lots of water and by wind.
  • There are multiple Oahu sailing vessels on all coasts of the island..
  • 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.
  • 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.

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.

Do you still have questions about Sailing Charters?

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

Sailing Charters Sorted by Specific Tour


Sailing Charters Sorted by Company

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(11 Reviews, 5 Stars)

North Shore Catamaran Charters

5 Activity Options

40' Sailing Catamaran, 40' Catamaran

The beautiful North Shore of Oahu provides the seascape for one of the most majestic boats on the island, the Ho'o Nanea, operated by North Shore Catamaran Charters. This 19 passenger, 40' sailing catamaran is one of the fastest on the island and offers fabulous sunset cruises, picnic snorkel sails and whale watching in season.
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(7 Reviews, 5 Stars)

Port Waikiki Cruises

4 Activity Options

54' Catamaran

If sailing is truly your ultimate objective in going out on a boat you will be thrilled with a ride on the sailing boat Paragon. The Paragon is a 47' sailing catamaran that is designed for these waters and designed for speed. There are not that many boats that pass through these waters that could go faster than this one.
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(4 Reviews, 5 Stars)

Bike Hawaii

3 Activity Options

Bike Adventures, Mountain Bike Tours

The company 'Bike Hawaii' deals with much more than just bike rides. Over their long history they have evolved to include hiking tours and kayaking trips as well as snorkeling and sailing adventures. Common ground for all these tours is a desire to take the island visitor to out of the way places and provide an ecological perspective.
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(3 Reviews, 5 Stars)

Tradewind Charter

5 Activity Options

Sail Oahu, Private Sail and Snorkeling, Private Sailing, Sunrise Sails, Snorkeling Tours and Memoria

Tradewind Charters specializes in private charter tours. The maximum of only twelve passengers on the 43 foot sailing yacht creating an intimate non crowded atmosphere. With additional options for catering or an on-board bar guests can really create their own adventure at sea. If you're on Oahu for a vacation or event check out Tradewind Charters.
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(1 Review, 5 Stars)

Iruka Hawaii

1 Activity Option

Dolphin Snorkel Tours, Manta Tour, Whale Watch

Iruka Hawaii offers snorkel and dolphin watch tours off the coasts of the two islands in Hawaii that provide the very best venue for observing dolphins, the Waianae Coast of Oahu and the Kona Coast of the Big Island of Hawaii.
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(1 Review, 5 Stars)

Holokai Catamaran

3 Activity Options

Reserve a trip with the Holokai Catamaran

Go out on an adventure with Holokai Catamarans! Discover colorful tropical fish, green sea turtles, exotic coral reef and more of Hawaii's undersea life. Dolphins are also possibilities on this incredible adventure. Snorkeling in Hawaii is very fun and easy.
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(3 Reviews, 4.7 Stars)

Makani Catamaran

2 Activity Options

65' Sailing Catamaran

One of the most beautiful sailboats sailing the waters off the coast of Waikiki is the Makani Catamaran. This 64' x 32' Cat is one of the very fastest on Oahu often achieving speeds of over thirty knots. Flush with the most modern amenities you will be able to enjoy a wonderful sunset sail, a coastal daytime sail and a snorkeling excursion.
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Hawaii Nautical

1 Activity Option

Leid Back' Dinner Cruise, Snorkeling and Dolphins, Whale Watch off the leeward coastline,Oahu Scuba

Hawaii Nautical offers a large variety of boat tours throughout the island of Oahu and on the Big Island of Hawaii. Snorkel tours and dolphin watches are offered in the mornings and the afternoons and in addition they offer sunset sails, dinner cruises, scuba and snuba options, whale watching in season and private charters.
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Holokai Kayak Adventure

1 Activity Option

Kayak off Kaneohe

Blessed with some of the most calm, clear and beautiful snorkeling waters in the state Kaneohe Bay is the location that is visited by Holokai Kayak and Snorkel Adventure. You will enjoy the bay and the sea life but will also get a chance to kayak out to the film location of Gilligan's Island. These guided kayak tours are wonderful but if you would like to rent a kayak on your own, that can be arranged as well.
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Maita'i Catamaran

1 Activity Option

Waikiki Sailing Charters and Booze Cruises

The 44' sailing catamaran, Mai Tai, has been one of the most popular boats we have ever had on Waikiki Beach. Leaving right from the sand between the Sheraton and the Halekulani this 47 passenger boat will take you out for a day sail, a snorkel or a sunset sail and a view of the Waikiki Coastline and Diamond Head.
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Royal Hawaiian Catamaran

1 Activity Option

52' Catamaran, 52' Catamaran - Sunset Excursions, 52' Sailing Catamaran, 52' Catamaran - Sunset Excu

One of the most beautiful catamarans to ever grace the waters off the coast of Waikiki is the 52' Rudy Choy designed custom cruising catamaran, the Royal Hawaiian. This famous boat builder built this specific boat with the expressed purpose of sailing Hawaiian waters. The boat is used for snorkel and sailing trips as well as private charters which can include dinner, sunset, star watching and whale watches.
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Sail Oahu

4 Activity Options

SV Shalimar is a 67 foot Mega Yacht

Experience Hawaii and the Pacific Ocean aboard your private yacht, Shalimar. The meaning of Shalimar in Sanskrit is "Home of Love on the Water".
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Recent Reviews


Top Activities
Customer Favorite Tours Based on Reviews

Let's face it. Sailing boats go way back in the history of human civilization.

Even here in Hawaii, without the sailboat, the Polynesians would have probably never found Hawaii. Columbus found America, on sailboats. Magellan sailed around the world. Sailboats are a part of our DNA as people, and in Hawaii we have lots and lots of sailboats to enjoy and to participate in.

We've got sailing on all of the islands, and Oahu is no different. Let's pull up a map. On Oahu we've got a lot of different boats that do sailing. There are a relatively small percentage of these boats that actually sail specifically for the purpose of sailing, a cruise that goes out only to sail. Usually the sailing is involved with other activities, like Snorkeling or a Dinner Cruise perhaps, maybe a Whale Watch. Just getting out on the water to do a number of things, and sailing is included if you're on a sailboat. Everybody likes to get the sails up and to enjoy them, enjoy the process of getting them up in the wind and having them billow and fill.

But that's usually just a portion of what we do on the sails that we have here on Oahu. There are some exceptions. There are a few Sunset Sails that go out, maybe 90 minutes, put up the sails and that's kind of the reason for that trip. Mai Tais might also fit into a part of that reason. There may be some boats that go out for a trade winds sail and just to see how fast they can go out in the channels and so on.

But most of the boats that you're going to find are going to include sailing with something else. Which is okay, the something else is good too. So there's a number of locations that we have throughout Oahu that you can catch boats that do sailing. Certainly off the coast of Waikiki and Honolulu. Ko Olina and Waianae are areas that we will also have sailboats. The North Shore, Haleiwa would be another place. Off the coast of Kailua in this area as well. So we're rich in boats that have sailing capacity here in Oahu. Just look through all the choices, see what you like. You might like a catamaran, you might like a mono hull, we've got a number of varieties, and we'll see what we can do.

So if you have any questions about Tours or Activities in Hawaii, just give us a call, or check out tombarefoot.com. We're here to help.


Sailing in Hawaii whether it be on a Hawaii sailboat charter, a Hawaii boat tour or a Hawaii yacht charter is simply a way of life in the islands. Keep in mind that the very first people to come to these islands came by virtue of a sail boat and so the sailing heritage runs deep in the waters surrounding Hawaii.

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Kauai sailing, with its sailing boats offering snorkeling trips, snuba adventures, snorkeling from shore, family snorkeling activities and various other tours involving sailing off Kauai are among the most interesting tours that Kauai has to offer.

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The stiff Maui's trade winds provide for great Maui sailing trips. If the notion of Maui sails intrigues you, you've come to the right spot. The Maui sailing climate and prevailing winds provide the best possible sailing environment.

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Sailing charters on the Big Island of Hawaii generally depart from the Kona side of the island. Because Kona is usually protected from the stiff tradewinds by the enormous volcanoes behind, these sails are often gentle in nature and are a great way to experience the beauty of Hawaii's ocean and sealife.

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