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
Trilogy Excursions
Maʻalaea Harbor & Lahaina Harbor
Pacific Whale Foundation
Lahaina Harbor
Four Winds II
Maʻalaea Harbor
Maui Custom Charters
Maʻalaea Harbor
Island Star Excursions
Maʻalaea Harbor
Sail Maui
Maʻalaea Harbor & Lahaina Harbor
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.