Cuesta Rey Cigars was founded in 1884 by Angel LaMadrid Cuesta and Peregrino Rey. They formed the company in Ybor City (the cigarmaking capital of Florida) and they made cigars using Cuban tobaccos (a style known as "clear Havanas"). In 1958, Angel's son sold the company to J.C. Newman of the J.C. Newman Cigar Company. To this day, the famed J.C. Newman factory in Tampa still has the giant Cuesta Rey Cigars sign atop the building.

In the 1980s, production of Cuesta Rey cigars moved to the Fuente factory in the Dominican Republic. Cuesta Rey still has their classic branding but has developed a more modern flavor profile at an affordable price point. Their portfolio currently ranges from mild to full in body, with releases like the Cuesta Rey Caravelle, the Cuesta Rey Centenario, and the Cuesta Rey Centro Fino.