Tuscany has many hill towns. Such towns invite day trips for exploring and wandering, with unexpected bits of history, art, and culture. Have good walking shoes and anticipate walking up and down hills. During tourist season parking is at a premium – particularly in hill towns. If you’re fortunate enough to find a parking space, there is likely to be a good walk to the city center. For some towns, taking a bus or train makes more sense as finding parking seems considerably difficult unless you arrive by car very early in the day.
We made a day trip from Montepulciano across Valdichiana to Cortona. Cortona is the town associated with Under the Tuscan Sun by Frances Mayes. The Commune (think of county) of Cortona extends well into the valley. The actual town is high on a hillside, and the highest part is surprisingly high above the valley. From across the height on a clear day can be seen farms, vineyards and orchards of Valdichiana in a vast expanse. Cortona is near the border with Umbria, and to the south in Umbria is Lago Trasimeno, the largest lake in Italy. The town is rich in history involving St. Francis of Assisi, and many references and places related to this saint are in Cortona.
On the heights above Cortona is the Basilica di Santa Margherita di Cortona. It is striking church with a beautiful interior. Included is Santa Margherita’s resting place. In many of the cathedrals and basilicas, there are the resting places, with bodies visible, of saints, cardinals and a few popes on display, and many of the faithful come to venerate and pray to these saints.
Cortona consists mostly of narrow streets and stairs, with some relatively small piazzas. The larger of the piazzas is Piazza della Republica, with a large city building dominated by a clock tower. It is the type of town made for wandering and sensing what it might have been like to live in medieval Europe.
Cortona was a town frequently visited by St. Francis. The Convento di San Francesco, houses personal items of St. Francis. Francis also established a retreat not far from Cortona that includes a cell that he used.
A pleasure of living in rather than being a two week tourist in Italy is that you get to visit small town and villages. Within sight of Montepulciano on top of another height is Montefollonico. It is a pleasant little town, just right for a stroll or stopping at a restaurant or bar (a “bar” in Italy is more like a snack bar and hang out than an American bar). There are houses with courtyards and loggia.