Although these days everybody seems to have been to Tuscany and most have visited Florence, Lucca, Siena and Chianti, huge areas of the region remain quite unknown, not only to tourists generally but also to the Tuscans themselves.
For instance, who has heard of Castiglion Fiorentino? More to the point who can pronounce the name? And yet this small medieval town in the southeastern part of Tuscany is most definitely worth a visit. Many people have been to Montalcino and some have seen Boccaccio’s birth place Certaldo. Take the general impression of these towns but with fewer tourists and you have Castiglion Fiorentino.
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The town is placed on a hilltop and on a hot summer’s day when “climbing” to the fort at the top it feels like a small mountain. The charming little streets are filled with restaurants and cafés and yet not so many that you suspect they are there for the benefit of the tourists. It is picturesque and peaceful in a way no longer found in the more central Tuscany. Quite simply nothing beats sitting at a café under Vasaris loggia in Piazza del Municipio.