Wilson's efforts in education have spanned a wide range. In the mid-1970s he taught math in the Boston Public Schools. He has served since 1980 either as Trustee or as a Corporation Member of the Sea Education Association in Woods Hole, MA, a fully accredited college-level deep sea oceanography institution that sends its students to sea. And he similarly served, from 1981-2000, as a Trustee or Corporation Member for The School for Field Studies, an accredited field school institution which sends its college-level students to 6 field research stations worldwide to learn. He also served as Overseer for the Museum of Science in Boston from 1993-1996.

Wilson holds an A.B. Degree in Mathematics from Harvard College in 1972, an S.M. Degree in Interdisciplinary Science from M.I.T. in 1976, and an M.B.A. Degree from Harvard Business School in 1982.

In 1980, Wilson was skipper and navigator aboard the Overall Winner, Holger Danske, in the Newport-Bermuda Race in a fleet of 162 competitors. In 1988, Wilson won Class V in the Carlsberg Singlehanded Transatlantic Race aboard the 35' wing-masted trimaran Curtana.

In 1990, aboard the 60' trimaran Great American, Wilson, with Steve Pettengill as co-skipper, challenged the 76-day world record from San Francisco to Boston by way of Cape Horn set by the clipper Northern Light in 1853 during the California Gold Rush. Wilson connected the voyage to 400 classrooms by newsletter and daily telephone recordings. In a raging Southern Ocean storm 400 miles west of Cape Horn, their 60' trimaran Great American was capsized in 65' seas on Thanksgiving Day. Re-righted an hour later by a monstrous wave (a first in maritime history), they were rescued dramatically at midnight by the giant refrigerated containership New Zealand Pacific. 

In 1993, Wilson tried again with Great American II, with Bill Biewenga as co-skipper, and set a new world record of 69 days 20 hours for the voyage. The new record was certified by the Guinness Book of World Records. The voyage pioneered the genre of 'interactive learning adventures' with an elaborately orchestrated interactive feature on Prodigy that reached 100,000 kids, and an 11 part series written by Wilson aboard Great American II at sea, and published by 12 major U.S. newspapers that reached 13 million readers weekly, and 250,000 classroom students.

Wilson authored a book on these voyages entitled Racing a Ghost Ship (1996, Walker & Co., NY, NY). The book won the 1997 Scientific American Young Reader's Book Award.

In 1990, Wilson, a lifelong asthmatic, was honored as Superachiever by the American Lung Association. And in 1993, he was the recipient of the First Annual Christmas Seals Hero Award from the American Lung Association of Massachusetts.