On June 20, 1916, he married Phyllis Sears, daughter of wealthy Bostonian
Herbert M. Sears, in
Beverly Farms. In 1924 the couple hosted
Edward, Prince of Wales. One of their sons,
Herbert Tuckerman, would follow his father into politics. She filed for divorce on December 6, 1940, in
Las Vegas, New Mexico, citing cruelty. Tuckerman stated that he had expected the action and would not contest it. On August 10, 1946, Tuckerman married Milicent Ewell Whittall at a private ceremony in
New Hampshire. and photographer
Jane Tuckerman. Milicent continued to breed horses following Tuckerman's death. Her horses included Rise Jim, winner of the
Tom Fool Handicap in 1981 and 1982. She died on December 3, 2003, at the age of 94. ==Death==