[Gertrude Conaway Vanderbilt with Friend at a Costume Ball]

An avid sailor, Gertrude and a friend pose in costume, possibly at a Vanderbilt party in Newport or Palm Beach. 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. In 1937, the Vanderbilts sailed Rainbow, successfully defending the America’s Cup for the second time, with Gertie aboard as timekeeper, observer, and afterguard and Mike as skipper.