If you really want the wind to fill the sails, consider the afternoon sails when the tradewinds are blowing the strongest.
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 Sailing Charters on Maui |
 America II - 12 Meter |
| Cinderella - 50' Columbia Sailing Yacht - Private |
| 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 |
Maui Sailing Charters
(From: $38.99 - To: $1,225.00)
The stiff Maui's trade winds provide great Maui sailing adventures.
If you like to sail, the Maui sailing climate and prevailing winds provide the right spot to be. 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.
Types of Maui sailing boats
- Sail on a 12 meter, $10 million, 1987 America's Cup Challenger
- Sail Maui's 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
- 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: $38.99 - To: $38.99) |
Cinderella The “Cinderella” is a fifty-foot columbia ocean sailing yacht. They only do private charters on this ship, taking groups of up to six passengers. The “Cinderella” can do private snorkel sails, performance sails, whale watching or sunset sails. There are a variety of snorkeling destinations that are within a quick sail from their slip at Ma’alaea Harbor. Chances are whatever sort of sailing trip you’d like to do we can help you arrange it aboard this classic sailboat. Even though this boat is…(more info) | Price Range: (From: $240.00 - To: $569.90) |
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…(more info) | Price Range: (From: $89.00 - To: $89.00) |
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…(more info) | Price Range: (From: $46.99 - To: $130.89) |
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…(more info) | Price Range: (From: $45.90 - To: $93.90) |
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: $1,225.00 - To: $1,225.00) |
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…(more info) | Price Range: (From: $59.00 - To: $234.00) |
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 to…(more info) | Price Range: (From: $189.00 - To: $234.00) |
This page contains information about: maui sailing, maui sail, maui sailing charters.
Hearing Impaired - Read the full transcript for this page's audio narrative.
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.
