There are 29 products in this category that range in price from $59.00 to $4200.00.
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?
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.
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
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
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
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
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.
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
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,
Design your own custom charter for you and your private group.
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
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
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.
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
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.
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
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
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.
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.
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
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
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
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
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
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
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.
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
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