Driving up to Castiglione d'Orcia had lots of switchback curves to conquer, but I made it. Driving these Italian roads is challenging but loads of fun for someone like me who loves driving. The wide vistas were breathtaking, at every hairpin turn a new elevation and new views. This "Rocca" (castle keep) set on a high precipice was amazing. There is a fortress (the Fortezza Aldobrandesca) on one mountaintop and a tower (Rocca di Tintinnano) on its close neighbor. It looked like something out of King Arthur or the Lord of the Rings... pretty fitting since this has been a settlement since the eighth century AD. You can really imagine the fortress defending this little duchy from invaders making their way up from the valley far below.
When we got to the top there was a very naturalized looking area with parking, a cafe and walking paths. The little cafe gave us great views, ice cream pops, sodas and a surprise-- spotty Wifi! We took a walk along the brick path along the edge of the cliff--pretty scary at times with poorly maintained shaky wooden handrails and uneven brick path. There were spots that had slid away entirely down the cliff, so we decided not to go further.
Yet another hilltown under our belts...