The collection contains slides, pre- and post-revolution photographs of Havana, correspondence, and tourism ephemera, such as a golf score card and postcards, collected by the family of John Olson while living in Cuba from 1952 to 1960. Mr. Olson's father worked for the Royal Bank of Canada in Cuba during this time.

The collection contains a letter, envelopes and a medallion relating to Cuban senator, mayor, and historian Manuel Martínez-Moles (1863-1951). The collection also includes a copy of "Manuel Martínez-Moles" written by Dr. Juan L. Riera for The Cuban Philatelist. Subsequent donations have included photographs of Cuban monuments in Miami, taken in 2020; restaurant and culinary ephemera; clippings and articles related to philately and Cuban historical figures such as José María Heredia, Félix Varela, León Primelles, and José Martí, authored by Dr. Riera; exhibition ephemera; political flyers; documents related to the Cuban communities in Ybor City and Key West; conference materials related to the InterAmerican Institute for Democracy, held in August 2022; and tourism ephemera. The collection also contains memorabilia such as matchbooks and cigarette ration coupons.