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Sailing Charters on Maui

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There are 39 tours in this category that range in price from $52.90 to $4900.00.

Sailing Charters

The stiff Maui's trade winds provide 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.


The trade winds generally come up in the later morning and the afternoons.


Where do Maui sailing charters sail?



  • The good stiff winds are usually with us in the afternoon so Maui sailing trips in the morning and evening are of a lighter nature. They're just as fun, just easier-going.

  • Of all the activities we have sent people on over the years, none has been more popular or has provided more positive feedback than our Snorkel trips to Molokini. People just love it! It's a perfect destination - only a forty-five to sixty-minute cruise out of Maalaea Harbor.

  • One popular Maui sailing tour is the trip to Molokini. The mornings have extremely light winds occasionally allowing for a gentle sail out (if the winds are strong enough to sail at all) but by late morning the winds are generally howling and make for a fun return trip.

  • Sailboats ply the waters up and down the coast of West and South Maui, stopping at secluded beaches, anchoring in rocky inlets, or hugging mountainous cliffs that plunge deep into the ocean. Some are out-and-out sailing trips, seeking out the wind line far out in the channel; other Maui sailing vessels combine Snorkeling or light-line fishing in calmer waters.


The time of year can affect your Maui sailing charter as well as the time of day:

As you are well aware, Maui is an island completely surrounded by water and consequently any ocean location off the coast of Maui has the potential to be an area where sailing can occur.


In fact however, there are only certain portions of Maui that are suitable for sailing on a regular basis because of the prevailing winds.


The most dominant of the prevailing winds are the trade winds which reach Maui approximately 300 days out of the year.


These winds will come out of the north-east during the spring, summer and fall months and primarily hit the north and eastern shores of the island.


Although trade winds occur in the winter as well, this is also the time we can receive winds which hit the island from the opposite direction (called Kona winds) and in many cases can include stormy conditions.


As far as Maui sailing charters are concerned it is usually best to depart from a location that is not particularly windy for logistical reasons and once out to sea, sail into the winds.


This makes the departure points of Kaanapali, Lahaina and Maalaea particularly suitable for a place from which to embark on one of the Maui sails.


In addition to the time of year the winds forming in the late mornings and afternoons are generally much stronger and for those that really look forward to a stiff Maui sail this would be your best option.


Types of Maui sailing boats:



  • Sail on a 12 meter, $10 million, 1987 America's Cup Challenger.

  • Sail Maui waters on a 65x25 foot, state of the art, multi-million dollar custom sailing catamaran with a 90' Wing mast.

  • Sail in a 50' Santa Cruz Sailing Yacht that won the 1984 Victoria to Maui Yacht Race.

  • Sail Maui's western shore on a 64' Sea Runner Catamaran.

  • Enjoy a 47' Maui sailing catamaran that is one of Maui's fastest.

  • Sail with a company that runs a series of Maui sailing catamarans ranging from a 55' sloop Rigged Catamaran to a 64' Searunner Cutter Rigged Catamaran.



Pride of America Cruise Ship:

Sailing Charters on Maui will not pick up at the cruise boat pier but these Sailing Tours on Maui can be reached via a Rent-A-Car that can be arranged through Tom Barefoot's Tours and you can be picked up by the Rent-A-Car shuttles right at the cruise ship dock. The majority of these Maui sailing excursions are available on the Sunday or Monday of your Maui cruise itinerary.

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


Recent Reviews


Sailing Charters Sorted by Specific Tour


We sell tickets to 39 items in the category Sailing Charters on Maui.

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Displaying 39 of 39 Results

$110.90

Sail from West Maui's beautiful coastline. Daily destinations are based on the current weather conditions. They often go to either the Cliff House, Olowalu, Honolua Bay or Lanai. This large sailing…

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$102.00

Join Hula Girl for a relaxing West Maui premiere snorkeling excursion on a beautiful sailing catamaran. In the spring and summer this tour usually goes to Honolua Bay, where there is an incredible variety…

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$1600.00

Choose the one of a kind beautiful sailing catamaran "Hula Girl" for your next private-charter excursion. Different seasons boast special attractions but all year Maui has wonderful things to see and experience…

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$4900.00

Set sail from Maalaea Harbor and anchor along the southern shore in a remote, secluded area of Lanai. Snorkel, swim and sunbathe. After a delicious BBQ, watch the sunset as you're returning to Maui.…

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$2800.00

Set out for a half day of sailing and snorkeling aboard the luxurious Island Star. Search for dolphins and turtles, sail or just relax and sunbathe on the decks of this 57 foot luxury yacht.

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$1375.00

Sail away from the crowds aboard your own private yacht. Choose to experience performance sailing in the Pailolo Channel or leeward sailing in the 'Au'Au Channel. Snorkel with an in-water guide at a local…

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$825.00

Set sail in the calm leeward waters of Lahaina and discover the beauty of catching the wind. Relax and enjoy 360 degree views as the sun sets and lights up the islands of Maui, Molokai and Lanai. A private…

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$185.00 - $232.00

This boat conveniently departs from the beach in front of the Makena Beach and Golf Resort, making it ideal for those staying in the Wailea and Makena area. Come aboard the Kai Kanani II as it departs…

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$1300.00

Snorkel like a pro while you see turtles, tropical fish endemic to Hawaii, and enjoy some of the Pacific's best dive sights. Shadowfax is equipped with the very best snorkel and safety gear. and offers…

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$99.00 - $650.00

With NOAA's Hawaiian Islands Humpback Whale National Marine Sanctuary located right in Kihei, whale watching is the best in the world in Maalaea Bay. Every year the same whale community commutes from Alaska…

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$325.00

Make your dreams come true by customizing your trip aboard Shadowfax. Your crew with 30 years experience in Hawaiian waters can help you have the time of your life. Go sailing, snorkeling or enjoy a beautiful,…

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$99.00

Enjoy two hours of tradewind sailing on Shadowfax. Maui's tradewinds offer great sailing all around Maui County, this is the perfect vessel to experience the freedom of moving on the wind along the water.…

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$109.00

Book this Sunset whale watch and enjoy 2.5 hours on the water at a spectacular time of day. Every year the same whale community commutes from Alaska to birth their calves around Maui in our warm, safe…

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$105.89

Reserve the Honolua Bay Snorkel Sail and go aboard Ocean Spirit, a luxury sailing catamaran, and cruise along the beautiful Ka'anapali Coastline. A continental breakfast and lunch with a colorful souvenir…

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$109.90

Let the wind catch the sails and you are off to Maui';s most visually stimulating snorkel destination. This five hour morning snorkel trip features a continental breakfast, buffet lunch, snacks, beer,…

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$64.90

Sailing out of Maalaea Harbor provides some of the best speed sailing in the world with flat water and stiff breezes. We often reach speeds in excess of 20 knots. This three hour trip features two hours…

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$174.90

The adventure begins in Lahaina Harbor where we set sail across the Au'au' channel to Lana'i. A continental breakfast featuring some of Hawaii's tastiest tropical fruit is served as you enjoy the panoramic…

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$133.90

This is a unique tour with no pre-planned destination. After about an hour's sail it's the Captain's choice of where your destination and the best snorkel spot of the day will be. Spend some time exploring…

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$67.50

Maui is a special place to see the humpback whales. Feel the wind and "sail" with these gentle giants. Each year they migrate from Alaska to make Hawaii their home. The Au'au channel off the coast of Maui…

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$106.90

Choose this Pride Premier Morning Molokini Snorkel for a deluxe two destination snorkel, snuba and scuba excursion featuring an island style continental breakfast and a hot BBQ lunch! A friendly crew will…

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$450.00 - $3175.00

This wonderful Power Flybridge catamaran is an ideal private charter boat for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling,…

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$450.00

Explore the island of Lanai's world famous dive sites. Choose from up to forty different dive sites from Cathedrals to Shark Fin Rock. Spinner dolphins are common sightings around the island of Lanai.…

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$98.90

This 4 hour excursion includes two hours of sailing and two hours of snorkeling. A knowledgeable crew will guide you through the pristine reef along the Lanai and Maui shores and afterwards you will enjoy…

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$61.90

Enjoy two hours of sailing off the majestic West Maui Coast, and enjoy a beautiful sunset at sea while you sit back, relax and let us do all the work. Whale watching when in season, December-May.

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$1200.00 - $2100.00

Design your own custom charter for you and your private group.

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$52.90

Enjoy two hours of real sailing. This voyage will take you along the West Maui coastline. Take in the sun, wind and salt spray as the island trade winds fill the sails. Whale watching is also available when in season.

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$52.90

Relax and enjoy the trade-winds as you sail silently along in Maui's crystal clear water, on a wind-powered sailing vessel, no engine noise so you can enjoy the quiet of the world.

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$124.90 - $1000.00

This is the only catamaran departing from Kaanapali Beach that will take you to Lanai for a snorkel, sailing adventure. In search of West Maui's best snorkel sites, you set off for the island of Lanai…

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$105.90 - $1000.00

Depart from Kaanapali beach and set off in search of West Maui's best snorkel sites for the day, based on current water conditions. Enjoy your breakfast and coffee that has been prepared by Chef Joey and…

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$218.42

This trip is what Trilogy is best known for. Depart from Lahaina Harbor at around 10:00 am (occasionally there is a sunrise departure at 6:30am). Start your day with an island style breakfast of Mama Coon's…

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$138.19

Explore the crystal clear waters of Molokini Crater and Maui's coastline, the home of the Hawaii honu (sea turtle). As you sail from Ma'alaea Harbor, enjoy Mom Coon's home made cinnamon rolls…

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$133.73

Snorkel, swim and discover snuba from Honolua Bay to Olowalu with views of Moloka'i, Lana'i and the West Maui Mountains. Snorkel (weather permitting) at an alternate site may be chosen if undesirable…

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$60.62

Delight in this amazing two hour whale watch leaving from Kaanapali. You start off a little wet as you load directly from the beach through the surf onto the boat! Aboard this catamaran Trilogy naturalist…

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$88.26

Experience a idyllic sunset sail exploring the West Maui coastline surrounding Kaanapali. Enjoy Maui's legendary kamakani (wind) with Trilogy. They really put the sails up then while you take it all in…

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$60.62

Leave from Maalaea for this amazing two hour whale watch! Trilogy is dedicated to sharing accurate information about the endangered humpback whale and its habitat with guests through on-board naturalists.…

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$60.62

Enjoy this amazing two hour whale watch leaving from Lahaina! Trilogy is dedicated to sharing accurate information about the endangered humpback whale and its habitat with guests through on-board naturalists.…

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$132.84 - $132.84

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, your…

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$124.81

Sail with Trilogy to "Maui's Mother Reef" and experience one of the largest turtle cleaning stations in Hawaii! Relax and enjoy a later departure, a continental breakfast along the way, before arriving…

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$132.84 - $132.84

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the west side of Maui. After mooring in a protected cove, enjoy…

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Sailing Charters Sorted by Company

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(9 Reviews, 5 Stars)

Maui Ocean Charters

5 Activity Options

Maui Ocean Charters

Set sail with Maui Ocean Charters on their sailboat "Shadowfax". Trips are available that last anywhere from a few hours to a few days or more!
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(5 Reviews, 5 Stars)

Makena Boat Charters

1 Activity Option

Makena Boat Charters

If you're staying on the south shore of Maui in the Kihei area, Wailea or Makena a really good choice for a snorkeling tour would be on the 65' sailing catamaran "Kai Kanani". This boat was built in 2007 and is a state of the art custom motorized sailboat. The location of the departure point for this boat is one of the very best because it is located just off the coast of Molokini, perhaps a short fifteen minute ride away.
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(2 Reviews, 5 Stars)

Gemini Charters

1 Activity Option

64' Sailing Catamaran

Gemini Charters offers sailing tours that depart off of Kaanapali Beach and has done so for over 30 years. They offer multiple tours which include a sail and snorkel up the coast to Honolua Bay when weather permits, a delightful champagne sunset sail and whale watching tours in season. Their seaworthy 64' Sea Runner Sailing Catamaran is an excellent choice for a real sail.
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(1 Review, 5 Stars)

Island Star

2 Activity Options

57' Sailing Yacht - Private charter only

The Island Star is a sail boat that is in a category of its own. This 57' sailing Columbia Yacht can accommodate as many a twenty guests and is used exclusively for private charters.
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(1 Review, 5 Stars)

Kainani Maui Sailing Charters

2 Activity Options

Kainani Maui Sailing Charters

Her modern yacht shape, spacious interior, and blue water sailing capabilities make her the perfect Hawaii sailing charter boat. She is also available for Memorials at Sea or Ash Scattering Services and special requests.
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(29 Reviews, 4.9 Stars)

Paragon Sailing Charters

5 Activity Options

47' Sailing Catamaran

Certainly one of the very fastest boats found in the islands is the 47' customized sailing catamaran, Paragon. Paragon Sailing Charters offers a number of choices for boat tours ranging from morning sails to Molokini; Day Trips to Lanai; Sunset Sails; and Performance Sails.
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(21 Reviews, 4.9 Stars)

Scotch Mist Sailing Charters

5 Activity Options

50' Sailing Yacht, 50' Santa Cruz Sailing Yacht

The Scotch Mist is a 50' Santa Cruz Sailing Yacht which carries 18 passengers and offers sailing and snorkel charters off the coast of Maui. Having been the winner of the coveted Victoria to Maui Yacht Race in 1984, this vessel is a perfect choice to enjoy the waters off the coast of Maui and Lanai. She offers sailing and snorkel tours, sunset sails, trade wind sails and whale watching in season.
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(48 Reviews, 4.8 Stars)

Trilogy Excursions

10 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to Molokini, 55' Sail Catam

One of the most popular and respected boating companies on Maui is the Trilogy which has been in operation here since 1973. Though being a large company now, operating six or so 50' range sailing catamarans, they are still the family owned operation that was begun by Eldon Coon and his two sons, Jim and Randy. Today they offer sailing tours to Lanai, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
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(6 Reviews, 4.8 Stars)

Hula Girl

2 Activity Options

65' Sailing Catamaran

You would be 'hard pressed' to find a more beautiful sailboat on Maui to take out on a snorkel sail, whale watch, dinner or sunset sail or a private charter. This multimillion dollar state of the art 65'x35', 90' wing mast sailing catamaran is designed for sailing and for maximum comfort. In addition it comes with its own full galley and private chef so all your meals will be prepared custom just for you.
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(8 Reviews, 4.8 Stars)

Pride Charters

1 Activity Option

65' Maxi Catamaran, 65' Catamaran

The Pride of Maui is one of the largest and most stable power catamarans available in Maui's fleet of boats. Leaving from Maalaea Harbor the 'Pride' offers tours to Molokini in the mornings but will also operate beautiful sunset cruises a few times a week and in addition will provide one of the most comfortable boats for whale watching in the winter months.
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Pacific Whale Foundation

1 Activity Option

52' and 60' Power Catamaran, 52' and 65' Power Catamaran, 65' Power Catamaran, 65' Catamaran

The Pacific Whale Foundation is one of the main companies we have on island that goes out in search of the whales during the winter months. In addition, throughout the year they also offer boat tours to snorkel at Molokini, dolphin watches that look for dolphins and snorkel off the coast of Lanai and have rigid hull inflatable tours that visit the back side of Lanai.
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Privacy Charters

2 Activity Options

Sailing, Power Catamaran

Privacy features a large air conditioned cabin with a couch seating for 3 guests, table seating for four, or sit in either of the two captains chairs at the lower helm station. Further forward there is a large clean restroom on the port side, and stateroom with a queen size bed on starboard side.
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Sea Maui

2 Activity Options

Make reservations for a snorkel trip or sunset sail on the Sea Maui.

Sea Maui is a beautiful 51 foot power, sailing catamaran that departs out of Kaanapali Beach. They offer a trade-wind sail every afternoon, a sunset sail in the evening and snorkel trips in the morning. Food is specially provided by renowned Chef Joey Macadangdang the former corporate executive chef of Roy's Kitchen.
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Top Activities
Customer Favorite Tours Based on Reviews

If you're interested in sailing, Maui is a good place to visit.

What do you need to sail? Basically you need water to sail on. We're an island. We've got water all around us. We need wind, a significant amount of wind. Maui is blessed to have trade winds that come in sometimes 300 days a year, somewhat less in recent years as weather adjusts, but these are the prevailing winds that Hawaii has always had and really provide a suitable environment for sailing. The winds generally come up in the afternoons. Morning on normal days, regular trade wind days, things are pretty flat in the morning, if not even glassy.

Then as we get into late morning and then early afternoon and then mid-afternoon, the wind really kicks up. It usually dies down somewhat in the early evening. We still may have what they refer to as temperature differential wind, a little bit lighter, more of a breeze, that can happen at that time of day. If you're really looking to go out to sail, you want to do that in mid-afternoon. We have boats that go out specifically for the purpose of catching that mid-afternoon wind and doing some serious sailing.

A few of the boats just do that, and others will take advantage of Snorkeling and that sort of thing. But that's really it. A distinction that you need to make before you decide to go out sailing is, do I want to go on a boat that just sails, in which case you're going to be pretty much limited to doing a mid-afternoon performance sail where you're going out just getting into the wind and doing that? Those are usually a couple hours. You might be able to do a little bit of a Sunset Sail, which you put the sails up and they get a little bit into the wind, but that's more about the sunset, I think, and the cocktails and that kind of an agenda.

The other way to do it is to take any one of the common Snorkel Trips that we have, the ones that go out to Molokini or the ones that go out to Lanai, and then of the boats that do this, choose one that is a sailboat. What'll normally happen is that at some point during the day, you'll have an opportunity to be on a boat that's going to put up all the masts and they're going to get into a little bit of a trade wind ride. You're going to get a combination of the Snorkeling or whatever else your day entails as well as the sailing.

Sailing is a lot of fun here. Our boats go really fast. Some of them go extremely fast. We've been on boats before that are 20 to 25 miles an hour, and you just pretty much have to hold on to whatever's near you as you're ripping along on the sea. It's a wild ride, lots of fun. Sailing's cool on Maui. 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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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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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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