Pilots Point Sailing School, Westbrook

Overseeing more than 22 New England locations, Jack Brewer—a lifelong sailor—has tended to boats and provided peace of mind for their owners for nearly 50 years. At their 50-acre marina community, Brewer Pilots Point Marina’s year-round staff works to keep the family-friendly facility’s swimming pool, restaurant, clubhouse, and more than 800 boat slips in ship shape. Sailing schools for juniors teach recreational and competitive skills, and adult-oriented classes introduce students to sailing or help them brush-up on hoisting sails, maneuvering, and reading the wind based on the ripples in a pitcher of beer. Summer slips and events offer boating and entertainment through the warmer months, and indoor-storage options keep skiffs safe from Old Man Winter’s icy beard-cicles.