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Take the autostrada A-1 Firenze - Roma motorway, heading south in the direction of Rome. As you enter the motorway, you will pass through a toll booth where you must take a ticket. Drive south until you reach the Val Di Chiana exit at the town of Bettole, located between Monte San Savino and Chiusi. Pay toll (avoiding Viacard and Telepass lines) and turn right at the sign for Perugia. (Italian motorway on-ramps are much shorter than in other countries and you may need to halt completely before being able to join the motorway traffic, rather than being able to merge into the traffic. It is compulsory to turn on your headlights on motorways and most Italian motorists have them on at all times)
Heading east in the direction of Perugia, you will pass the exit signs for Foiano di Chiana, Cortona, and Castiglione del Lago as you approach the northwest corner of Lake Trasimeno. Stay on this little highway for approximately 15-20 minutes, exiting at Tuoro. Come off access ramp and turn right, following the signs to Umbertide.
Stay on this road, which soon crosses another perpendicular road (take care at this intersection), as it winds its way up into the old town of Tuoro. When you reach the centre of the old town, at the top of the hill, turn left, following the sign for Umbertide.
The winding road up the hill will lead up a little mountain (if it's a clear day, you can look backwards and get beautiful views of Lake Trasimeno) and then down the other side, twisting and turning. When you get to the bottom of the hill, the road forks. Take the left hand fork for Mercatale di Cortona (a very small town not far from the fork in the road).
Just before entering the town, there is a Total gas station on your right. On your left is a small cluster of stores, including the Conad grocery store, a good place to shop for provisions (open Monday through Saturday 8:30 till 7:30, except between 1-4:30 every day; also closed all day Sunday and Wednesday afternoon).
Just after the “Conad” store, the road turns sharply to the right. Instead of following the road to the right, take the left turn immediately after a butchery, signposted for Cortona. It is a tight turn on a narrow road between buildings so look out for oncoming traffic. Follow this road as it widens then begins to climb. Soon after the uphill portion begins, you will see the medieval castle of Pierle. Look out for a right turn just past the castle. Take this turn and wind uphill for a short distance until you see the signs for Country House Rocca Di Pierle. Continue a little past the property until you reach the gate for the guest parking area at the rear.