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Sailing Charters on Kauai

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There are 12 tours in this category with adult prices that range in price from $89.00 to $209.00.

Kauai Sailing Charters

Sailing Tours and Charters on Kauai are delightful.


Kauai sailing tours are among the most serene, relaxing and meditative tours that Kauai has to offer.


Kauai sailing tours can also be among the most exciting, adventure full and thrilling tours that Kauai has to offer.


Kauai's coastline is both varied and beautiful ranging from the more gentle inlets and coves of the Poipu and south shore region to the dramatic, isolated and incredible shoreline of the Na Pali Coast.


Kauai has a number of sailing boats and sailing charters offering sailing trips that traverse the Kauai shoreline which is often teeming with marine life.


Dolphins are very often a part of the marine landscape on many of the sailing charters and the whales seen off the Kauai coast during whale season are often many more than the island is generally given credit for.


Many Snorkeling areas also include extensive coral reefs and a full complement of reef fish.


Kauai sailing trips can often be more robust than those on other islands as Kauai is the first island to intercept the stiff trades that blow from the North East.


Because many of the sailboats on island are also used for Snorkeling please check with our Snorkeling section of the site for additional details.


Norwegian Cruise Line - Pride of America Cruise Ship:

Sailing Tours on Kauai will not pick you up at the cruise ship pier. Your best bet is to either arrange for a taxi to take you to and from the departure location or to have Tom Barefoot's Tours arrange for a Rent-A-Car shuttle to pick you up at the cruise ship pier. The best timing for most of these Kauai Sailing tours is going to be on the Thursday or Friday of your cruise schedule.

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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(9 Reviews, 5 Stars)

Blue Dolphin Charters

2 Activity Options

56 foot wide-beam sailing Trimaran, 27' Raft and 63' Catamaran

Blue Dolphin Charters offers spectacular motor sailing cruises to the NaPali Coast of Kauai and to the 'forbidden island' of Niihau. In addition Blue Dolphin also offers whale watches, snorkeling, snuba, dinner cruises, sunset sails and rafting excursions. All emphasis is placed upon customer comfort and its large boats each maintain large walk-in restrooms, fresh water showers and plenty of deck space.
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(4 Reviews, 5 Stars)

Catamaran Kahanu

1 Activity Option

36' Sailing Catamaran, 36' double hull Hawaiian Catamaran

Catamaran Kahanu is a boat tour company that offers tours of the spectacular NaPali Coastline on Kauai's North Shore and also offers dinner cruises and whale watches. With a maximum capacity of only eighteen passengers these tours are very personalized and your captain and crew are of Hawaiian ancestry and have been lifelong residents of Kauai.
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(13 Reviews, 4.8 Stars)

Kauai Sea Tours

3 Activity Options

24' Rigid Hull Inflatable Rafts, Lucky Lady' 60' Sailing, Power Catamaran

Kauai Sea Tours is a large charter boat company that offers tours off the coast of Kauai and particularly the NaPali Coast with its beautiful 'signature' boat , Lucky Lady. In addition it also provides romantic dinner cruises and whale watches and also has a fleet of specially designed raft boats which are great for exploring caves, snorkeling and racing dolphins.
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(47 Reviews, 4.8 Stars)

Captain Andy's Expedition

5 Activity Options

55' Sailing Catamaran, 55' Gold Coast Yachts, 30' and 38' RAIV

Captain Andy's Sailing Adventures for years has offered tours to see the spectacular NaPali Coastline of Kauai. Sailing large and luxurious Gold Coast Yacht Sailing Catamarans, Captain Andy's will take you snorkeling and dolphin watching as well as provide romantic dinner and sunset cruises. In addition you can enjoy rafting adventures to the NaPali Coast.
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(8 Reviews, 4.8 Stars)

Holo-Holo Charters

1 Activity Option

61' and 48' Sailing Catamarans, 38' Raft

Holo Holo Charters offers a variety of boat tours on Kauai on large, powerful and stable catamarans. Tours include beautiful snorkel and dolphin watch excursions to the NaPali Coastline, raft tours of NaPali during the summer months, dinner sunset cruises, whale watching and tours to the forbidden island of Niihau.
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Well this little video is about sailing and sailing excursions on the island of Kauai.

Actually before we talk about the actual sailing excursions themselves, it'd probably be a good idea to talk about the wind conditions because that's where all the sailing is generated from. We've got winds that happen throughout Kauai, throughout the entire year.

The vast majority of the winds that are buffeting Kauai are trade winds. Trade winds come from the northeast, generally come from this direction. They're caused by high pressure systems, up to the north. They provide fairly stiff breezes and a constant between five and 20 miles per hour, generally speaking. Used to be, we'd say they would hit 300 days out of the year.

Actually as the decades have been adjusting here, we actually have less trade wind weather. It's down to about 220 days a year, something like that on most years. In the reverse of that, is what we call the kona winds. Those come from the southeast. They come from the opposite direction. Those will generally happen during the winter seasons, but they will provide stiff breezes, sometimes actually way too much wind.

You can do sailing all year round. The two months that actually have the least amount of wind that you'll find are going to be September and October. But anyway, that's the wind situation. We've got wind so you can go sailing.

Now, how many boats actually go sailing? Well not as many as you might think. Generally speaking people ask about sailing charters, sailing, just sailing, that's all they want to do. That usually isn't the way it works. Usually, we've got boats that go out Snorkeling, go out to Napali, going to areas throughout the islands, and they are sailboats. They have a sail on board. They will put up a sail at some point in time and do some sailing. It's usually an addendum to a snorkeling trip or some other trip you might be out on.

But there are a number of these boats that we have that you'll be able to enjoy, some going out of port Allen, others out of Nawiliwili harbor.

That's the story on sailing. 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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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.

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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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