An Islander ’44, "Shadowfax" is a blue water sailer having logged multiple South Pacific trips. So many comforts of home including private berth, spacious lavatory and a galley that brings superior culinary presentations, all offer passengers a great home base for exploring Maui, Lana’i & Moloka’i. Her beautiful interior boasts imported teak detail throughout. Families of up to six & groups of two couples would be very comfortable on over-nighters.

Take your own sailboat sailing in the beautiful Ma’alaea Bay, renowned for its steady breeze and crystal clear water. We can leave anytime you’d prefer to sail, snorkel and whale watch . A six hour private is the perfect amount of time to do several snorkeling spots, and sail around the bay. Whatever you ‘d like to do, we would like to customize a trip especially for you.

Begin by sailing around beautiful Maalaea bay which offers steady offshore winds and calm water. We then sail over to West Maui’s breathtaking Pali cliffs and pull in along the shoreline for our own private snorkeling spot.

Tucked beneath the cliffs are large coral outcroppings that make for beautiful underwater topography and snorkeling. We have a variety of sites along this coast that are some of Maui’s premier snorkel sites, including Coral Gardens. Only accessible by boat, you and your family can get away from large crowds and enjoy the peaceful serenity of a more private and tranquil spot.

Join us for your own Private Sunset Sail. Perfect for celebrating birthdays, anniversaries, proposals, bachelorette parties, quality family time, and more! Light appetizers and non-alcoholic beverages such as water, juices and sodas are provided but you are also welcome to bring alcohol on board. We have all the appropriate glassware for serving.

With NOAA’s Hawaiian Islands Humpback Whale National Marine Sanctuary located right in Kihei, whale watching is the best in the world in Maalaea Bay. Every winter the same whale community ‘commutes’ from Alaska to birth their calves around Maui in our warm, safe waters.

Take your loved ones and friends sailing on your own boat with the help of a few crew! If desired, Shadowfax offers a hands-on learning experience for those who wish to learn about sailing! Not only are we Maui’s only zero emission tour boat with our electric motor but it means we actually sail the entire trip!

Unlike may others companies that motor the majority of the time, we pride ourselves in sailing as much as possible. Come relax with us and learn about humpback whales during whale season from our marine certified naturalists!

Sail away into the sunset with us here on Shadowfax!

She is also available for overnight charters. Customize your excursion to include fishing, and snorkeling in the crystal clear waters of Maui, Lanai, Molokai and Oahu. Shadowfax prides itself in our commitment to the quality of your experience aboard. Our overnight charters allow you to enjoy Hawaii ’s marine sanctuary in a way unlike any other, to explore our beautiful marine life, breath-taking sunsets, untouched beaches, and our seasonal North Pacific humpback whales that grace our waters every December.

Let the ocean slowly rock you to sleep in comfort underneath thousands of stars. Our complimentary food and drinks are locally sourced and served according to passenger preferences. There’s nothing more adventurous than sailing the Pacific! It’s a dream come true! Book Today!




Pricing upon request.