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The best way to travel within the region, making it possible to explore tiny hill towns and country restaurants, is by car. The roads are better north-south than east-west, so allow time for excessively winding roads when heading east or west. Sometimes it's faster to go a little out of your way and get on one of the bigger north-south routes.
The A1 (Autostrada del Sole), which runs from Florence to Rome, passes close to Arezzo. Cortona is just off the highway linking Perugia to the A1, and Sansepolcro can be reached from Arezzo on the SR73, with Monterchi a short 3-km (1½-mi) detour along the way.
Though Arezzo is the third-largest city in Tuscany (after Florence and Pisa), the old town is pretty small, and is on a low hill almost completely closed to traffic. Look for parking along the roads that circle the lower part of town, near the train station, and walk into town from there.
Just as in Arezzo, in Cortona the city center is completely closed to traffic, and the few parking areas sprinkled outside the city walls don't make it easy to park. The majority of Cortona's streets are very steep. Fortunately, most of the main sights are grouped near the Duomo in the lower part of town, but if you want to visit the upper town, be prepared for a stiff climb.
For visits to the mountainous National Park of the Casentino and the smaller towns and villages farther to the east, such as Sansepolcro and Monterchi, a rental car is almost a necessity: bus schedules can be difficult to plan around, and train service is either infrequent or nonexistent. All make for rewarding day trips, though a fair part of your time will be spent on winding, beautiful, country roads. If you want time to explore, plan to stay the night.
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