Italy is divided down the middle by mountains usually referred to as the Apennines. Midway down the boot-shape that we recognize as Italy the region to the east of those mountains is known as the Emilia Romagna on the coast of the Adriatic Sea. To the west lies Toscana (Tuscany) on the coast of the Tyrrhenian Sea. West of the Apennines to the north is the Piemonte where foothills climb into the Alps. To the south the high hills of Tuscany dissolve into the rolling farmland called Umbria, the bread basket of Italy. As mentioned, the Tuscan region is mostly high rolling hills bathed by the clearest of atmospheres and sunlight that has inspired Artists for centuries. With wonderful exceptions (Florence, Siena, Pisa etc.) the region is mostly agricultural and is home to the finest vineyards and orchards where some of Italy’s finest wines and olive oils begin. Chianti is a region within Tuscany where wine of the same name originates, and vineyards wind their way over some of the most spectacular vistas imaginable.
Almost every hill top throughout Italy has an ancient structure on it. Usually these are medieval fortresses (rocce) or castles (castelli), sometimes monasteries. Around these battlements towns have developed over the centuries. During the wars of the Dark Ages the walls of these fortresses were extended outward to encompass the towns. Most of the towns and cities of Italy still have remnants of these city walls. Many are almost wholly intact with modern cities growing up around them, leaving the old cities within as they were. Inside these walls the small winding streets are often impassable to cars, accessible only on foot. Since these are hill towns many of these walks are vertical to one degree or another, and you will often be joined by the village residents of all ages, some quite remarkably old, especially by American standards, to be making such an ascent. It is a thrill in itself to walk on pavements perhaps more than 2000 years old, often layered over the top of streets from even older civilizations, mingling your footsteps with all those who went this way before you.