Sailing Charters

Come Sail Aboard Shadowfax

Your crew with 30 years experience in Hawaiian waters can help you have the time of your life.


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.

If you really want to see Maui, you have to get off that pool chaise and get on the boat. Shadowfax crew customizes private yacht charters to make your trip the best part of your Maui Nui experience. Maui has so much to offer, but you can’t see it from your hotel.


Maui’s tradewinds offer great sailing all around Maui County (Maui, Lana’i & Moloka’i). Shadowfax is the perfect vessel to experience the freedom of moving on the wind along the water.


Large pods of spinner dolphins travel between the Hawaiian islands. They frequent Hulopo’e Bay (Lana’i) virtually on a daily basis. These beautiful marine mammals are always a special encounter.

Whale Watching:

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

Pupus & Cocktails:

Enjoy the best in on-board catering with Shadowfax’s crew customizing menus with your preferences incorporated into our up-scale presentations. Featured here: Lava Lamp Cocktails with fresh crudité of Maui-grown vegetables with bleu cheese & crab dips.

Private Charters

Shadowfax is available for custom private charters for groups up to six persons at $375/hour, two hour minimum.

Price includes Pu-pu’s and soft drinks. Alcohol is welcome and BYOB.

To Book, Call