Optimo cigar label for A. Santaella Cigar Company featuring Sr. Antonio Santaella, 1900.

Antonio Santaella opened cigar factories in New York in 1889, in Key West a few years later and in Tampa in 1905. His factories distributed their cigars in Chicago, the Mississippi Valley, the West, and as a publicity stunt shipped a carload of their cigars to Nome, Alaska. The company’s leading label was “Optimo” meaning “the very best.”

Source: University of South Florida Special Collections

Key West Blossom Cigar Label made in 1904 by the Fernandez Brothers Cigar Company.

Source: University of South Florida Special Collections

Advertisement for Key West cigars.

Source: George A. Smather’s Libraries

Talmaege Culmer, one of the original Key West cigar makers, is seen hand rolling a cigar at the Key West Cigar Factory in Pirate’s Alley. The factory has been selling cigars since 1963. Photo was taken between 1975 and 1985.

Source: Florida Photographic Collection