Tom Hollyday

Tom’s career on traditional boats began over a decade ago, when he replied to a craigslist ad to be a “Ticket Booth” seller for a schooner company. In his mid 20’s, with nothing better to do, he accepted the job and thus started on his career path as a dedicated steward of traditional sailing vessels. After working his way up as a deckhand, cook, engineer and business manager he earned his 100 Ton Captain’s licenses and began running vessels all over the country, From Maine to Key West, all the way down to the San Blas Islands in Panama. Along with his trusty sidekick Buddy, a 10 year old Nova Scotia Duck Tolling Retriever, he is passionate about keeping the history and heritage of traditional sailing vessels alive. Tom is extremely excited to share the history of Hesper, and the basics of how to sail and properly maintain a Pilot Cutter with Wooden Boat School students.