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Sailing Charters on "The Big Island" of Hawaii

See All Activities See All Activities By Vendor Big Island of Hawaii sailing charters often offer snorkeling as well as a sail.

There are 13 tours in this category that range in price from $70.90 to $2700.00.

Sailing Charters

Many of the Big Island of Hawaii snorkeling cruises that take snorkel trips to various Big Island of Hawaii Snorkeling spots also have the capability to sail as well and hence offer a special double bonus for Big Island of Hawaii sailing enthusiasts.


Sailing conditions on the Big Island of Hawaii are generally determined by the existing wind patterns.


Generally speaking, the majority of the time the "trade winds" blow consistently from the north-east.


These winds provide excellent sailing conditions and are the best conditions for Big Island of Hawaii sailing charters.


Although the trade winds blow most of the time there is no question that some times of the year are better than others.


In the months of May through September the average percentage of days that blow from the "trades" averages about 90% of the time.


In the winter months the average falls to about 60% of the time and in the month of January the percentage actually falls to about 40%. The time of day also has an effect on the amount of wind that blows and obviously affects the quality of sailing Hawaii's sailing charters can provide their clients.


Mornings are generally fairly calm but as late morning comes the trade winds will pick up.


By mid afternoon the winds are usually at their strongest and these are the best times to catch a real stiff sail.


As sunset approaches the winds usually decrease and settle down to a gentle breeze which is ideal for a romantic sunset sail.


Pride of America Cruise Ship: Many Big Island of Hawaii sailing charters are close enough to the arrival pier to allow you to take a taxi to meet them for a tour. Others can be best reached by renting a car from Tom Barefoot's Tours that will pick you up via shuttle at the pier. These Hawaii sailing boats are available when you arrive in Kona on the Wednesday of your cruise itinerary.

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

Sailing Charters Sorted by Specific Tour


We sell tickets to 13 items in the category Sailing Charters on "The Big Island" of Hawaii.

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

Displaying 13 of 13 Results

$145.00
(6 Reviews, 5 Stars)

Guests of all levels come snorkeling aboard the Fair Wind II. This 4 hour cruise includes 2 hours of snorkeling at Captain Cooks Monument in Kealakekua Bay. All the snorkel gear and instruction are provided.…

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$89.00
(2 Reviews, 4.5 Stars)

Come and enjoy a scenic coastal cruise to Kealakekua Bay. Guests will enjoy 1 1/2 hours of snorkeling time, with snacks, beverages and a no-host bar during the last hour of the cruise. Set out on this…

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$389.00

Hawaii Nautical takes you on an unparalleled yacht to experience the beauty and grandeur of the Kona coast and its most bejeweled underwater treasures at stunning snorkeling bays along the historic Kona…

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$2700.00

Sail to Kealakekua Bay and enjoy the scenic and historic Kona coastline. Snorkel Kealakekua's underwater marine sanctuary, in view of the Captain Cook Monument. See dolphins and turtles year round. During…

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$88.90

Three and one half hour snorkel trip to Pawai Bay, which is a protected area on private land that's located on the Kona Coast. Enjoy real sailing on Kona's only sailing catamaran. Snorkel amidst…

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$101.90

Save 21.43%
(5 Reviews, 5 Stars)

Weather permitting, you will head north looking for dolphins and get in the water for a once in a lifetime encounter. This is nothing like seeing them in captivity. You will be able to see them up close…

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$79.90
(7 Reviews, 5 Stars)

This tour usually departs around 5:00pm, arriving at the manta ray site in about 45 minutes. You can snorkel a bit before you watch an amazing sunset from the boat. Snacks, fresh island fruit, soda, juice…

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$84.90

Save 13.35%

Join us for a deluxe morning snorkel trip to Pawai Bay, a protected area on private land, located on the Kona Coast. Enjoy real sailing on Kona's only sailing catamaran. Snorkel and see rainbow colored…

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$91.90

Enjoy a morning of sunshine, motor out to a secluded snorkel site along the Kohala Coast, receive a short briefing and get geared up, descend on Winona's easy access "Stairway to the Sea" directly into…

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$121.90

Sail for about 45 minutes along the beautiful Kona coast to historic Kealakekua Bay. Your captain will select the best snorkeling sites for the day and your friendly and professional crew members provide…

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$107.90

Enjoy a beautiful Hawaiian sunset aboard the Hokulani, as you sail from Keauhou Bay into the setting sun (sailing times vary according to sunset). After sunset we drop sail and head for the World Famous…

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$70.90
(1 Review, 5 Stars)

Your captain will select the best snorkeling site of the day, in Kealakekua Bay, and your friendly and professional crew members will provide site briefings and historical facts along with snorkel tips…

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$1050.00

Join Wahine Charters for your customized private charter. The crew of Wahine Charters loves to fish, swim with dolphins, snorkel coral reefs and help others discover what the oceans of Hawaii have to offer.…

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Sailing Charters Sorted by Company

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(12 Reviews, 5 Stars)

Kamanu Charters Inc.

4 Activity Options

You'll enjoy "real sailing", snorkeling and whale watching on this trip with Kamanu Charters on their 36' custom designed sailing catamaran "Kamanu" to Pawai Bay. This area, located just north of Kona, is under State Fishery Management . The bay is within the Queen Liliuokalani Trust Land at Kaiwi Point and it is private. They also offer night manta ray snorkels.
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(1 Review, 5 Stars)

Sea Paradise

3 Activity Options

Sea Paradise is a 50 foot sailing catamaran, the Hokuhele, which explores beautiful locations along the Kona coastline. Trips depart from Keauhou Bay heading down the coastline towards the historic marine preserve, Kealakekua Bay. Dolphins or even whales when in season will often become a major focal point of these trips. Evening tours are also available to see the amazing giant Manta Rays.
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(8 Reviews, 4.9 Stars)

Fair Wind Charters

2 Activity Options

Well established as a tour boat company on the Kona Coast of the Big Island, Fair Winds Charters has two beautiful and distinctive boats that offer a complement of tours which include snorkel tours to Kealakekua Bay and evening Manta Ray excursions. Also included as a part of the day snorkels are SNUBA diving and the new sea rocket underwater propulsion vehicles.
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Hawaii Nautical

2 Activity Options

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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Mauna Lani Sea Adventures

1 Activity Option

The beautiful Mauna Loa Resort in Waikoloa is the departure point for all the activities provided by the Mauna Lani Sea Adventures. Pristine snorkel adventures, scuba diving trips, sunset sails and whale watching trips in season are all available. The 55' Polynesian style catamaran 'Winona' carries intimate groups of passengers on tours along this gorgeous coastline.
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Wahine Charters

1 Activity Option

Wicked Wahine Charters operates a series of boat tours out of Kailua-Kona on the Big Island. Their 29' custom power vessel can easily traverse the 12 miles of coastline between Honokohau Harbor and the Captain Cook Monument while snorkeling and dolphin watching on the way, or it can take you out on a night time Manta Ray adventure or whale watching.
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Video Transcript

So, how about sailing on the Big Island? We do sail there. We do have sailboats. We do have wind that can carry us along on the ocean. You may be surprised that we don't have as many strictly sailing-type ventures as you might think.

If you're a sailing purist and you just want to get out on a boat, and you want to sail, and that's what you want to do, we can do that. We do have some charters that will do that with you. The majority, however, are going to be sailing charters that actually do something else, like snorkeling or whale watching, and then do some sailing as a part of the trip, kind of on the periphery as an additional thing.

So, be careful which trips you choose, depending on what you're interested in doing. In all honesty, many people really enjoy sailing, but would want to include it with some snorkeling or some whale watching, that sort of thing, and then just have a portion of the day be sailing. But whichever category you fit in, we do have the capability of arranging this on the Big Island for you. Generally speaking, these are off the leeward coasts of Kona going up toward Waikoloa.

If you have any questions about tours or activities in Hawaii, just give us a call, or check out tom-barefoot-dot-com. We're here to help.

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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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On a windy day in mid-July, my son Jake and I set out on an afternoon sail that turned out to be one of the most exciting events of our whole summer. On board the catamaran was a handful of other folks who, like us, were in the mood for adventure.

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