North America Trip Leader

Bill Bailey

Bill Bailey acquired his passion for boats at the impressionable age of 12, when he worked at a shop with a master boat builder on a five-year project. At age 19, he bought a 32-foot engineless mahogany sloop and sailed her in the San Diego area for several years. In the 1980s, Bill and his family moved to the Northwest and began a fishing business, with Bill on the water at least 200 days per year aboard his 1936 wooden fishing boat. The Bailey family moved to San Juan Island in 1989. During this time they owned and voyaged on two classic cruising boats, the first a 1946 33-foot Monk design and the second a 1947 42-foot Bill Garden-designed commercial troller. Currently Bill spends more than 340 days each year at sea, and greatly misses gardening and dogs.

Our Team

Client Testimonials

Bill was an exceptional leader, guide, humorist, captain, and all around great guy. He really set the tone for the whole trip and fostered a great sense of community for a very diverse group of people living in close quarters.

Jennifer T.

Guttenberg, NJ
Alaska's Inside Passage

Bill could not have done a better job in organizing and executing all aspects of the trip. The expertise and passion he demonstrated was incredible. His intimate knowledge of boat operations and flexibility with regard to the schedule was admirable. We learned so much from him and will never forget the wonderful experience we shared.

Wayne H.

Tucson, AZ
Baja: Exploring the Sea of Cortez

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