Find the best sailing trip for your group by narrowing down the options using one of our tools. Try clicking on the map to find something close. Click a question to use our activity selector to narrow your options. Or, If you want to keep things simple you can always just browse through the list of all the sailing trips that we offer on Maui in the yellow box below.
 Sailing Charters on Maui |
 America II - 12 Meter  |
| Hula Girl - 65' Sailing Catamaran |
| Island Star - 57' Sailing Yacht - Private charter only |
| Paragon Sailing Charters - 47' Sailing Catamaran |
| Scotch Mist - 50' Santa Cruz Sailing Yacht |
| Shangri-La - 65' Sailing Catamaran |
| Trilogy Excursions - Kaanapali - Breakfast Sail and Snorkel |
| Trilogy Excursions - Lanai - Lanai |
Sailing Charters on Maui
(From: $43.99 - To: $3,800.00)
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Information Related to Sailing Charters on Maui |
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Do You Have a Boat that Goes Out Sailing with No Extras? |
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Whalewatch Sailboat Combo? |
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.
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 the1984 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.
Tom's Tips - Maui Sails
A hat with a strong chin strap is a great idea in the tropical heat and strong winds of an afternoon sail.
Keep one hand on some part of the vessel at all times. Sometimes you'll need both.
Want to take the helm? Don't be afraid to ask. Many captains will be happy to let you take over.
Looking for a real sailing adventure? Afternoons are best, check those out first.
Sailing Tours and Sailing Excursions in Maui - Options Below:
America II The America II was a 1987 America's Cup Challenger. This prestigious yacht was custom designed and built, at the cost of $10 million, for the sole purpose of competing in world-class racing. After completing her transpacific race she was retired from racing to do sailing tours out of Lahaina Harbor on Maui. She offers sailing trips during the summer and sailing/whale-watching trips during the winter. If you’re a fan of sailing or sailboat racing you will enjoy a sail on this world-class sailing…(more info) | Price Range: (From: $43.99 - To: $43.99) |
Hula Girl The Hula Girl is a brand new 65x35 foot, state-of-the-art, multi-million dollar, custom sailing catamaran with a 90' Wing mast with Spectra Sails and seating for up to 49 guests for an elegant lunch or dinner prepared in a commercial quality restaurant equipment kitchen and service at comfortable tables with cushioned seating and roll down vinyl widows with panoramic views during times of inclement weather. The vessel is stunningly beautiful, with sleek lines and hand painted graphics, including a larger than life Hula Dancer on each bow. A Fly Bridge that houses the helm station has couch type seating for 12 guests with 2 cocktail tables. This area gives the feel of a VIP lounge. The boat is also exceptional for snorkeling and equipped with all the best gear, including 18 scuba sets and it's own compressor to refill the tanks, easy water entry and return at the swimsteps, 3 on-deck fresh hot water showers, a women's changing and powder room with vanity.…(more info) | Price Range: (From: $97.00 - To: $97.00) |
Island Star The "Island Star" is a luxuriously appointed fifty-seven foot sailing yacht. She is certified by the Coast Guard to carry twenty passengers and she can sleep ten people comfortably. Available for custom private charters the "Island Star" can take you on a half-day, full day, sunset, overnight, or multi-night cruise. They can take you around the waters of Maui or Lanai if you want to stay close, or if you want to go on an extended adventure they can even take you island hopping to any of the other major Hawaiian Islands. To be out on a luxury yacht like the "Island Star" enjoying the company of your own private group surrounded by the alluring waters of Hawaii with the crew catering to your every need is an experience that is bound to please those that have the most particular of tastes. The whale sanctuary in the waters surrounding Maui is teaming with whales during the whale season in the winter and springtime. …(more info) | Price Range: (From: $2,200.00 - To: $3,800.00) |
Paragon Sailing Charters The "Paragon" and "Paragon II" are two of the fastest sailboats on Maui. With one boat in Lahaina Harbor for the Lanai trip and one in Ma'alaea Harbor for the Molokini Paragon Charters is set up to go to both of Maui Counties top snorkel destinations. Paragon Charters is known for taking small groups on their large catamaran boats and providing them with adventurous sailing experiences. These boats are capable of very high speeds and under strong winds they are regularly clocked at over thirty knots. If you are not familiar with sailing terminology, that is extremely fast. Paragon Charters will provide everything you'll need to go snorkeling including the snorkel mask, snorkel fins as well as floatation devices on request. Entry to the water is easy with the snorkel step that lowers of the bow of the boat down into the water.…(more info) | Price Range: (From: $45.99 - To: $135.99) |
Scotch Mist The "Scotch Mist" is a classic sailboat. This fifty foot Santa Cruz Sailing Yacht initially came to Maui in the 1984 Victoria to Maui Yacht Race, which she won. Since her racing days her owners have kept her in Lahaina Harbor using her to take the visitors on Maui on various sailing excursions. The waters in front of the Lahaina Harbor are ideal for a mellow sail. The channel is relatively protected by the West Maui Mountains compared to the open ocean, which makes for a more comfortable sailing experience. The ride of the "Scotch Mist" is much different then the larger catamarans that are very popular on Maui. The "Scotch Mist" is a monohulled sailboat with a large keel. This allows it to lean over into its line which can make for quite an exciting ride. "Scotch Mist" offers trips in the morning, midday and even a sunset sail.…(more info) | Price Range: (From: $55.90 - To: $101.90) |
Shangri-La Go sailing aboard the Shangri-La, a modern luxury cruising catamaran that was custom designed by her owner/operators who have chartered these waters for over twenty-eight years. This sixty-five foot sailing catamaran yacht features spacious air-conditioned living quarters and is certified for forty-nine passengers by the coast guard, but limited to six to eight guests on overnight trips. The Shangri-La Departs from the sands of Kaanapali Beach.…(more info) | Price Range: (From: $1,375.00 - To: $1,375.00) |
Trilogy Excursions Trilogy Excursions has been taking the visitors of Maui on sailing excursions for over thirty years. They go to such locations as Lanai, Molokini and the western coastline of the West Maui Mountains. Trilogy Excursions is a family business that was started by the Coon brothers and is now operated by their many sons and daughters. They have a reputation for maintaining an exceptional level of customer service on all of their trips. Their crew is friendly and attentive and will be waiting on you throughout the entirety of the trip. The "Discover Lanai" and "Discover Lanai Sunset" trip are the sailing trips that they are known for. The island of Lanai is one of crown jewels of Hawaii. The marine life here is abundant with the island boasting the largest unbroken coral reef in the state. Trilogy Excursions has been going to Lanai for years and they have constructed a pavilion and set up a series of beach chairs and hammocks for their guests to enjoy while they're on the island. Trilogy Excursions has always been known to pay a great deal of attention to detail, from their secret family recipes, to their mid channel toasts and their well practiced safety briefings they do not skip a beat in making sure that they go all out to ensure that their guests have a great time. …(more info) | Price Range: (From: $99.00 - To: $199.00) |
Trilogy Excursions - Lanai Trilogy has been operating sailing and snorkeling trips to Lanai for decades. They have been voted activity of the year many times and this is no doubt a result of the hard work and effort that was put into the company by the founders. The Coon brothers founded Trilogy over thirty years ago and now their sons and daughters help with the operations of their company. The Coon families' attentions to detail and genuine caring attitude have helped to build the excellent reputation that they have today. If you're looking to do some sailing over to Lanai then you should definitely look into the offerings from Trilogy Excursions. The design of their large luxury catamarans have been proven time and again with making these trips with ease for decades. Dolphins are commonly seen year round and humpback whales are often seen during the winter whale season.…(more info) | Price Range: (From: $199.00 - To: $199.00) |
Sailing Charters in Maui - As you are most certainly aware, the Hawaiian Islands are surrounded by ocean. In fact they’re surrounded by a lot of ocean essentially 2000 miles worth in every direction. It’s no surprise then that the earliest Polynesian peoples to arrive here in Hawaii from the “South Seas” came to the islands on sailing ships or catamarans. Since those early days “sailing” has been an integral part of the Hawaiian experience. These days we still have many sailing vessels that ply the waters off the coast of Maui. Many sail in conjunction with other marine endeavors such as snorkeling or whale watching but my favorite are the ones that go out for the expressed purpose of sailing. These are often referred to as “power sails” and usually take place in mid afternoon and make use of our predominant “trade winds” which blow strongest at that time.
