[Harold Stirling Vanderbilt and Gertrude Conaway Vanderbilt]

After her marriage in 1933 to Harold S. Vanderbilt (“Mike” to friends and family), Gertie sailed as one of the few women allowed on board racing J-class yachts in the 1930s. Aboard Rainbow in 1937, the couple successfully defended the America’s Cup for the second time, with Gertie acting as timekeeper, observer, and afterguard and Mike as skipper. They remained avid sailors and were inducted into the America’s Cup Hall of Fame in 1993.