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A week near Cortona

We will be spending a week at a villa about 20 minutes from Cortona in mid April. With traveling, we will probably have 5 days to "sightsee." We also want some downtime. Any suggestions on what towns to visit? We will have a car and are interested in food, wine, art, walking/hiking. Specific restaurant or winery recommendations appreciated.

Posted by
7175 posts

North - Arezzo
South - Orvieto, Montepulciano
East - Assisi, Gubbio
West - Siena, Montalcino

Posted by
715 posts

East and right close by is Perugia which so many people seem to miss. The Guild Halls are fantastic, as is the underground - the Rocca Paolina - which is not really an underground but the area of Perugia that Pope Paul covered over to build a fortress. There are several very nice Etruscan gates and the Town Hall is very nice.

Posted by
15161 posts

Just to name some of the closest (in alphabetical order):
Anghiari
Arezzo
Assisi
Castiglion Del Lago
Castiglion Fiorentino
Cortona
Chianciano
Gubbio
Lucignano
Montepulciano
Perugia
Pienza
Spello

Get a map, plot them in the map, and design a logical itinerary where you can see a couple a day. For example Montepulciano and Pienza are near each other. So are Assisi and Spello. My favorite is probably Anghiari.
Arezzo and Perugia are small cities (Perugia is not that small actually), rather than towns. Both are very historic and beautiful.