Start your Valtiberina adventures in the region’s largest town, Sansepolcro, best known as the birthplace of Early Renaissance master Piero della Francesca and custodian of some of his most famous frescoes. Although remembered primarily as a painter, during his heyday Piero della Francesca was also a mathematician.
The Museo Civico is the “mecca” for those on the Piero della Francesca path. Here you’ll find a high concentration of his frescoes and paintings, including the monumental Resurrection, famous for its allegorical references to the passage of time and the synthesis of science and art. Less instantly recognizable are the artist’s Madonna of the Misericordia polyptych and frescoes of San Giuliano and San Ludovico. In addition to Piero della Francesca’s work, the museum is home to precious pieces by Pontormo and Andrea della Robbia, plus a substantial collection of Santi di Tito’s work.
True art buffs should take the five-minute walk from the museum to the deconsecrated church of San Lorenzo (via Santa Croce 2) to see a stunning altarpiece by a certain late Renaissance-Mannerist redhead. Giovanni Battista di Jacopo, better known as “Rosso Fiorentino” (“the redheaded Florentine”) painted a monumental Deposition here that’s only a hair less lauded than the same scene he painted for the Pinacoteca Comunale of Volterra.
For a break from the typical art-themed itinerary, consider a round of cigar shopping: Sansepolcro has been prime territory for tobacco plant cultivation since at least the 16th century, although historically the cigars themselves were then fabricated in Florence.