The Classic Boat Collective and Bucks Harbor MarinaA famous shipwright once said, “There isn’t anything wrong with taking care of something,” reflecting his lifelong love of wooden boats. He understood—as do we—that being part of the classic boat world isn’t just about sunny days and fair winds, but about the lessons these boats teach along the way.
The Classic Boat Collective’s mission is to provide affordable, community access to some of the most iconic sailing designs in the world. We welcome sailors of all ages and abilities, with the goal of making time on the water accessible, engaging, and rewarding.
The Classic Boat Collective is proud to partner with Buck’s Harbor Marina, giving our staff the opportunity to learn how to maintain, sail, and care for one of the most distinctive fleets in the world. Many of our team members also serve as instructors at local yacht clubs, making this a natural partnership—one we hope will inspire and support future generations of traditional sailors.
Our Team
Tom Hollyday
Tom’s path on the water began on the business side of the industry. In his early twenties, he answered an online advertisement for a summer ticket booth position—took a chance on it—and never looked back. What followed was seven years of “crawling through the hawsepipe,” working his way through roles as deckhand, mate, watch officer, assistant cook, and chef. During that time, he sailed extensively, from Penobscot Bay to as far south as the San Blas Islands in Guna Yala.
More recently, Tom completed a four-year stewardship aboard the Luke Powell pilot cutter Hesper. During his tenure, Hesper underwent a full restoration and was awarded the 2022 Mendelowitz Award for Most Photogenic Vessel at the Eggemoggin Reach Regatta—a testament to the dedication of the entire team surronding him. At the same time, Tom founded and operated Canvas + Pine Sailing Expeditions, offering private, bespoke sailing trips aboard Hesper out of Camden, Maine.
Tom is currently the General Manager at Buck’s Harbor Marina and is excited to bring his extensive marine operations experience and entrepreneurial spirit to the Classic Boat Collective, helping grow it into a strong and welcoming community initiative.
Founder