Maui Sailing

Unique Maps • Best Charters • Sailing Tips

Maui Sailing Activites

There’s more to do on the water than just sail! We suggest taking a sail boat to go snorkel at Molokini, scuba diving at Lanai’s Cathedrals, enjoy cocktails during sunset, or go whale watching in season. Sailing for the sake of sailing is worth the trip alone, but why not enjoy the islands many great activities while sailing?

Maui Departure Points

We’ve put together some custom maps, directions and photos of the various harbors in Maui to help you navigate your way to your next sailing excursion.

Maui Sailing Charters

Kai Kanani

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 in Makena, south Maui.

Trilogy Excursions

The Trilogy family have been sailing the Pacific for over a hundred years, about half of which has been within the Hawaiian Islands.  Their new fleet of sailing catamarans have some of the best service and more interesting sailing destinations (including Lanai.)

Trilogy Excursions

The Trilogy family have been sailing the Pacific for over a hundred years, about half of which has been within the Hawaiian Islands.  Their new fleet of sailing catamarans have some of the best service and more interesting sailing destinations (including Lanai.)

Four Winds II

Four Winds was specifically built for the winds of Maui, Hawaii. This 55 ft catamaran sails from Maalaea Harbor and has some unique features like a glassbottom viewing room, waterslide and onboard video production.

Pacific Whale Foundation

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!

Pacific Whale Foundation

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!

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 (808) 875-0333

Gemini Charters

Kaanapali Beach Entry
64ft Catamaran (808) 669-1700

Island Star Excursions

Maalaea Slip #42
57 ft Sailing Yacht (808) 669-7827

Kai Kanani

Maalaea Harbor Slip #56
65ft Catamaran (808) 879-7218

Maui Classic Charters

Maalaea Harbor Slip #80 & 55
55ft Catamaran (808) 879-8188

Maui Sailing Canoe

Beach Entry at Polo Beach
At the Fairmont Kea Lani Hotel
(808) 281-9301

Pacific Whale Foundation

Ocean Spirit at Lahaina Harbor Slip #4 luxury catamaran

Paragon Sailing Charters

Maalaea Harbor Slip #72
47ft Catamaran 1-800-441-2087

Shadow Fax

Maalaea Harbor Slip #70
Private yacht and Live Aboard Sailing Cruises (808) 874-1110

ShangriLa Private Charters

Lahaina Harbor Mooring
65 Ft Sailing Yacht (808) 665-0077 

Teralani Sailing Adventures

Kaanapali Beach Entry
65 ft Catamaran (808) 661-7245 

Trilogy

Maalaea Harbor Slip #99 & #62, and in Lahaina too!
50 ft Catamaran (808) 874-5649

Where Should We Sail?

Maui is composed of multiple islands that are easily in reach while sailing. Cruise to the protected waters of Molokini Crater to snorkel, snuba, or scuba dive. Snorkel at Turtle Town and see loads of turtles and other ocean life. Or make the journey to the island of Lana’i to explore spots few visitors have seen.

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.