Make sure you have plenty of gas in the tank, because Perugia is well worth a detour. Situated 40 miles from Piancastagnaio, it offers a few fabulous attractions, such as Piazza IV Novembre and Rocca Paolina. Arezzo is another road-trip destination to keep an eye out for. It’s situated just 45 miles away. If you make the trip here, Cathedral of Saints Peter and Donato and Basilica of San Francesco should be on your must-do list.