Your next day trip, departing from Arezzo, will take you to a town made famous in the English-speaking world largely by Frances Mayes’ fixer-upper classic, Under the Tuscan Sun: charming Cortona. Long before Mayes ever set foot here, however, another Francis (this one with an i) came through town. Saint Francis of Assisi stopped here in 1211 and founde a hermitage called Le Celle not too far away. Another religious figure associated with the town is its patron Margaret of Cortona, who is celebrated in town-wide festivities on May 9.
A visit to the Museum of the Etruscan Academy and of the City of Cortona (MAEC) is a must: besides housing Etruscan vases, relics and the iconic Tabula Cortonensis (the two-millennia-old Cortona Tablet, perhaps its best-known piece), the museum documents the evolution of the town with impressive breadth, beginning in the Prehistoric age.
Next, if you’re interested in the area’s “native sons” of art, pop by the Diocesan Museum which is home to many altarpieces by the locally-born Luca Signorelli. Fra Angelico wasn’t a native, but several masterworks by him, including an Annunciation, are also here.
If your visit lands in summer or early autumn, keep an eye out for Cortona on the Move initiatives, exhibitions and spinoff events: this world-renowned photography festival offers a curated look at the finest work in contemporary photography and typically runs from July to October.
When hunger strikes at some point, indulge in a local specialty like a ciaccia, a savory fried bread made with bacon fat and prosciutto, washed down with a glass of Cortona DOC wine. Got more of a sweet tooth? Opt instead for the dessert variety (ciaccia con l'uva), which is made with grapes and olive oil instead
At sundown, start making your way toward Montepulciano, your home base for the next two nights, via an inexpensive train ride from either the Terontola-Cortona or Camucia-Cortona stations. The journey clocks in at just under one hour from either departure point.