The Convento de San Bernardino de Siena, founded in 1552 and finished in 1560, is one of the oldest religious buildings on the Yucatán peninsula. It sits at the western end of the Calzada de los Frailes, the long, cobblestoned street lined with pastel colonial houses that is Valladolid's most photographed view. The complex includes a fortified church, a two-storey cloister, and a walled garden.
The lower cloister hosts a small museum with religious art and archaeological finds, including objects recovered from the cenote beneath the convent. In the evenings (typically Wednesday–Saturday), a video projection mapped onto the facade tells the history of the town and the convent — free, well-staged, and very popular with locals.