Arcidosso, which is famous for its chestnut festival, is surrounded by winding mountain roads bordered with forests and steep slopes that in the winter transform into some of central Italy's prime skiing spots. The northern side of Monte Amiata, which we reach after Arcidosso, with its picturesque scenery, is the perfect spot to snap a photo.
After 4km on the the SP160, you'll come to a small walled town: Montelaterone. The romantically inclined will want to walk along kissing alley, called as such because it's so narrow you could kiss a passer-by coming the other way. Castel del Piano is known for its folklore; it even has a Palio that sees neighborhoods go head to head in horse races every year on September 8.
The road then curves to the right through the woods. The SP37 was once famous for its uphill race; ask Enrico, a motorbike enthusiast and manager of the Hotel Le Macinaie for stories about it. The winding roads here lead to the Prato delle Macinaie where the forests are sublime.
Heading towards the top of Monte Amiata and following Prato della Contessa, turn to the left where after five minutes you'll have ascended considerably. Back on the main road, which is now called the SP81, the curves are surrounded by impressive woodland that is particularly attractive in Autumn. Unfortunately the road is fairly worn down in areas because of the cold winters, so be careful.
A natural tunnel precedes Abbadia San Salvatore, which welcomes us with its medieval roads and Abbey: its crypt is breathtaking. From the SP81 to the SP18, the road remains beautiful and flowing. We head down to 772 meters above sea level at Piancastagnaio. Take a break and walk in the shade of Rocca Aldobrandesca. You can also visit some old mercury mines in the area
The loop goes on: the roads to the right take us to the top while those to the left leave the area. The road here has good grip. Head towards Tre Case,then Saragiolo and Santa Fiora on the SP6. As well as a pleasant sqaure, there's a fishpond and park here. Going onwards you will encounter Bagnore, once a spa town, before heading back to Arcidosso where there's the Teatro degli Unanimi di Arcidosso, an old theatre with a wide variety of shows. The castle museum is also not to be missed.