Perry Webster Gilbert was born in North Branford, Connecticut, on 1 December 1912, the oldest child of Scott and Hester Gilbert.  He had only one sibling, a sister Eleanor, who was born two years later. Like so many others who grow to cherish life in the sea, Perry's early interest in the ocean began with family trips to the seashore, led by his father, a carpenter and homebuilder.  At the beach, Perry and his father would fish, tread for clams, and enjoy a family seafood picnic.  From those pleasant childhood experiences, Perry developed a love for the sea and the life that it holds, a love that was to carry him throughout his professional career.

His early education in a one-room schoolhouse, where one teacher taught all eight grades, was not up to his mother's standards.  So young Perry was put through what he calls the biggest transition of his life, moving from the little country school in North Branford to a big city school of 600 students in New Haven, a 10-mile trolley ride from his home. There he was labeled a hick by the other students, until they learned he lived on a beautiful farm and if they played their cards right, young Perry would invite them out to his farm for the weekend.  By his last year at the school, Perry had become president of his class.