After selling the publications to Cahners Publishing, Syd focused on collecting and driving vintage cars and participating in historic auto racing. He was an owner and investor in the Sportscar Vintage Racing Association and developed the successful Vintage Motorsport magazine.
Syd married his first wife, Jan McNally, in June 1954. Jan died of emphysema in 1997. In 1999 he married Joan Hoffman, whose husband had died two months before Jan. Syd and Jan had four children and eight grandchildren.