The collection contains  a series of Whitehead’s diaries spanning the period of 1938 to 1981 (1941-1949 are not included). The diaries are filled with detailed, if taciturn, descriptions of Whitehead’s daily activities; every action, from eating breakfast to getting his car serviced, is given attention in the diaries’ pages. For example, each trip to and from Miami Beach is described, as well as Whitehead’s trips to South Florida’s restaurants and attractions.

The two photo albums in the collection are the product of a 1951 trip through Florida and the Keys; they offer interesting views of typical tourist destinations during the period. A series of color photographic slides from the late 1940s to the mid-1950s are concentrated solely on South Florida. Subject matter include views of Miami International Airport, Crandon Park, Hialeah Park, Lincoln Road, and a fashion parade along Miami Beach’s Lincoln Road.