Terry Bailey was born in Manchester in 1941. He gained a place at Manchester College of Art then pursued a career in advertising as an illustrator, eventually becoming freelance, working for many agencies in Manchester and London. Terry moved to the West Country in 1970 to concentrate on fine art and he opened his own gallery shortly afterwards. A life-long interest in boating, coupled with a strong maritime influence, resulted in a move towards marine subjects. In 1977, Terry submitted a painting to the Royal Society of Marine Artists which was accepted for the exhibition at the Mall Galleries, London. The following two years running at the RSMA he won the Classic Boat Painting Award. Terry was subsequently elected an Associate Member of the RSMA. In 2001 Terry was chosen to paint the trophies for first, second and third places of the J Class Round the Island Race of the America's Cup Jubilee taking place in Cowes from 18th to 25th August. These paintings were shown at the Royal Yacht Squadron, Cowes during the Jubilee. He and his wife continue to live in Cornwall.