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

sailing 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  on this luxury catamaran.

Trilogy Excursions

Maʻalaea Harbor

Trilogy Sailing
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.)

PacWhale Eco-Adventures

Maʻalaea Harbor

Pacific Whale Foundation

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

Four Winds Molokini
With over 30 years in the industry, Four Winds uses their experience to enhance your adventure.  Known for giving guests what they want, Four Winds allows for the most snorkel time (up to 2.5 hours) compared to other tours, and serves a fresh and hot “cooked to order” lunch.

Maui Custom Charters

Maʻalaea Harbor

Maui Custom Charters Sailing Tours

Enjoy a completely private sailing tour aboard the beautiful S/V Artemis, a 47′ Leopard sailing catamaran or the sleek S/V Nova, a 42-foot Catalina MKII sailing yacht. 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

Island Star Sailing

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

Sail Maui Maalaea Bay

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!

Sea Maui

Kaʻanapali Beach

Sea Maui Catamarans
Sunset sails, snorkel adventures, whale watching and even a Lanaʻi journey all from Kaʻanapali beach! Take to the water and sail on one of their sailing catamarans. Sea Maui prides itself on accommodating customer service and FUN tours from experienced sailors. Private charters are also offered.DN Approved

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.

Maalaea Harbor

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.

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

Maui Custom Charters Nova

Maui Custom Charters Nova

Maalaea Harbor Slip #103
42 Ft Sailing Yacht

Teralani Sailing Adventures

Kaanapali Beach Entry
65 ft Catamaran

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.