"Head for the Hilltop Make the steep ascent to this walled hilltop town and you’ll find yourself transported back in time—to the Renaissance, medieval, Roman, and even ancient Etruscan periods. Thought to be founded as far back as the 7th century B.C.E., Volterra is a favorite among the Tuscan hill towns for its spectacular setting and its wealth of notable sites. The latter range from the 1st-century B.C.E. Roman Theater and Etruscan-era city walls, gates, and tombs to the 13th-century Palazzo dei Priori town hall and cathedral (home to an array of sculptures and paintings). The Guarnacci Etruscan Museum showcases thousands of funeral urns from as far back as the Hellenic period, while the former Medici fortress—built in the late 1400s—now houses both a high-security prison and, several times a year, a gourmet pop-up restaurant staffed by inmates (reservations are hard to come by and, naturally, involve detailed security measures). Soak up the town’s rhythm at the main Piazza dei Priori, then browse the boutiques and workshops packed with artworks from massive sculptures to travel-friendly trinkets made with famous Volterra alabaster, another tradition dating back to Etruscan times."
