Maui Sailing
Unique Maps • Best Charters • Sailing Tips
Maui Sailing Charters
Below are some of the finest Maui sailing charters available. Most of them have realtime availability directly on our site. Book today before we’re sold out!
Kai Kanani
Maluaka Beach, Makena, South Maui
The Kai Kanani is a sailing catamaran that sails from Makena in South Maui, Hawaii. They’re one of the only vessel allowed to pick up passengers from the beach in Maui! Enjoy sailing conveniently from Maluaka Beach on this luxury catamaran.
Trilogy Excursions
Maʻalaea Harbor & Lahaina Harbor
PacWhale Eco-Adventures
Maʻalaea Harbor & Lahaina Harbor
Rooted in ocean protection, Pacific Whale Foundations seeks to use research, education, and conservation programs to keep our oceans healthy. From that, a fleet of vessels and a crew of conservationists allow you the opportunity not only to see the beauty of the ocean but to learn about how you can protect it.
Four Winds II
Maʻalaea Harbor
Maui Custom Charters
Maʻalaea Harbor
Enjoy a completely private sailing tour aboard the beautiful S/V Nova 42-foot Catalina MKII. As a private tour, you have the freedom to customize your own adventure, whether it be a whale watch, snorkel tour, or a full-day sunrise to sunset charter.
Island Star Excursions
Maʻalaea Harbor
With a welcoming crew and scrumptious onboard menu, a private tour aboard the elegant Island Star is a first-class experience. Departing out of Ma’alaea Harbor, this 57-foot luxury sailing yacht offers private snorkeling and whale watch excursions for up to 18 people.
Sail Maui
Maʻalaea Harbor & Lahaina Harbor
Onboard the Ocean Spirit, a new luxury sailing catamaran sailing from Lahaina Harbor, this is one of the most eco-friendly boats in Maui waters with loads of room. Whale watching in season, Honolua Bay and more await you!
Maui Sailing Canoe
Polo Beach, Wailea
Experience the Wailea Coast just as the early Hawaiians did with Maui Sailing Canoe. This thrilling adventure takes visitors on a sailing and snorkeling excursion aboard a modern outrigger canoe. Learn about Hawaiian navigation and history while watching for whales (in winter) and snorkeling one of Wailea’s pristine coral reefs.
GungHo Sailing
Lahaina Harbor
Sea Maui
Kaʻanapali Beach
Maui Sailing Activites
There’s more to do on the water than just sail! We suggest taking a sailboat to go snorkel at Molokini, scuba diving at Lanai’s Cathedrals, enjoying cocktails during sunset, or going whale watching in season. Sailing for the sake of sailing is worth the trip alone, but why not enjoy the island’s many great activities while sailing? And, if you’re looking for more, check out our 2-week Maui itinerary.
Maui Departure Points
More Maui Sailing Tours
When sailing in Maui, there are many options. Below are some Maui Sailing Tour boats. These boats are merely listed, and we don’t recommend one over another. We tried to put together the most comprehensive list possible.
Alii Nui
Maalaea Harbor Slip #56
65ft Catamaran
Gemini Charters
Kaanapali Beach Entry
64ft Catamaran
ShangriLa Private Charters
Lahaina Harbor Mooring
65 Ft Sailing Yacht
Teralani Sailing Adventures
Kaanapali Beach Entry
65 ft Catamaran
Where Should We Sail?
About Maui
Maui is the second largest island in the Hawaiian Island chain. It encompasses over 700 square miles (1883.5 Km square).
Maui County is composed of four islands of which Maui is the largest. Lana’i, Kaho’olawe, and Moloka’i surround the island of Maui, Hawaii. Kahoolawe is uninhabited. Lana’i is famous for scuba diving and plush Four Season’s Resorts. Molokai is known for its natural beauty and sea cliff waterfalls. Molokini Crater is a volcanic atoll, but not considered an island.
Sailing in Maui is one of the best ocean activities to do. Travel to one of the islands in Maui County and experience sailing the way it should be.