Charles Gregory was born and lived on the Isle of Wight, which informed his maritime subject matter. He worked in oils and watercolours as well as etching, and specialised in yacht portraits. He was a friend of John White, who owned the largest shipyard on the Isle of Wight, a connection that led to many commissions. He was a regular exhibitor at the Suffolk Street Galleries in the years 1848–1952. His work is included in the collection of the National Maritime Museum at Greenwich.