Home > Maui > Sailing Charters

Sailing Charters on Maui

Sailing Charters on Maui

There are 29 products in this category that range in price from $59.00 to $4200.00.

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 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.


We sell tickets to 29 items in the category Sailing Charters on Maui.

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

Displaying 29 of 29 Results

$69.00
(6 Reviews, 5 Stars)

Enjoy two hours of sailing off the majestic West Maui Coast, while enjoying one of our complimentary beverages-beer, wine, soft drink, or bottled water-while you sit back, relax and let us do all the work.…

More Info / Buy Now

$159.00
(5 Reviews, 5 Stars)

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…

More Info / Buy Now

$59.00
(5 Reviews, 5 Stars)

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…

More Info / Buy Now

$171.90
(4 Reviews, 5 Stars)

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…

More Info / Buy Now

$64.90
(4 Reviews, 5 Stars)

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…

More Info / Buy Now

$89.90
(2 Reviews, 5 Stars)

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.…

More Info / Buy Now

$205.00
(7 Reviews, 4.9 Stars)

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…

More Info / Buy Now

$129.00
(9 Reviews, 4.8 Stars)

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…

More Info / Buy Now

$109.90
(7 Reviews, 4.6 Stars)

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,…

More Info / Buy Now

$1200.00 - $1500.00
(2 Reviews, 4.5 Stars)

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

More Info / Buy Now

$94.90
(6 Reviews, 4.2 Stars)

This deluxe two destination snorkel, snuba and scuba excursion features an island style continental breakfast in route to Molokini Crater and a hot BBQ lunch. A friendly crew will give you expert instructions…

More Info / Buy Now

$119.00
(1 Review, 3 Stars)

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…

More Info / Buy Now

$4200.00

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.…

More Info / Buy Now

$450.00 - $2250.00

This wonderful sailing power catamaran is ideal for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling, cruising the coastline…

More Info / Buy Now

$2400.00

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.

More Info / Buy Now

$1250.00

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…

More Info / Buy Now

$750.00

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…

More Info / Buy Now

$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.…

More Info / Buy Now

$450.00

Cruise the north shore of Molokai, where the world's tallest sea cliff with spectacular cascading waterfalls will amaze you, or visit the secluded coves along east Molokai's tropical shoreline.…

More Info / Buy Now

$304.90

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,…

More Info / Buy Now

$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…

More Info / Buy Now

$114.90

Come aboard Ocean Spirit, a luxury sailing catamaran, and cruise along the beautiful Ka'anapali Coastline to the breathtaking waters of Honolua Bay, one of Maui's most popular snorkel spots. Enjoy a leisurely…

More Info / Buy Now

$124.90

This is the only catamaran departing from Kaanapali Beach that will take you to Lanai for a snorkel, sailing adventure. As you set off for the island of Lanai you will be offered breakfast and coffee prepared…

More Info / Buy Now

$109.00

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…

More Info / Buy Now

$105.90

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…

More Info / Buy Now

$101.90

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…

More Info / Buy Now

$59.00

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.

More Info / Buy Now

$129.00 - $129.00
(1 Review, 5 Stars)

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…

More Info / Buy Now

$101.90

Enjoy 2.5 hours on the water at sunset time and go whale watching. Includes hot and cold pupus. Bring your own alcoholic beverages. Every year the same whale community commutes from Alaska to birth their…

More Info / Buy Now


Filter your options by clicking a link on the keyword list below.