I recently holidayed in Tuscany staying in a small village called Montanare located about 2 miles outside of Cortona. Being so local, Cortona became the main stop most evenings for dinner and was one of the most buzzing towns I’ve been to in recent years.
Cortona is a typical hilltop town with stretching views in every direction. In fact Cortona offered some of the best scenery we experienced during our 10 day stay in Italy.
The main feature at Cortona is the 2 adjoining piazza’s which are surrounded by restaurants and gelato shops; incidentally, Snoopy’s is by far the best one in town!
The main ‘picture postcard’ feature of the town is the Palazzo Comunale:
In the evenings the town and these squares really come to life with street entertainment and a great vibe from the locals.
We ate in Cortona on several nights using Trip Advisor to steer us on the best places to visit. Personally I found that 2 restaurants stood out above all the rest. Firstly La Loggetta opposite Palazzo Comunale on the raised terrace:
The second restaurant that I really liked was just off the main Piazza called Preludio:
Parking at Cortona is particularly challenging with no real way of parking in the centre. You do therefore have to park on the outskirts of the town and then walk up the hill to the centre which is no more than a 5 minute walk. We found that parking on Viale Battisti was fine and found a space halfway up the hill every night. If you drive more than about half way up the road however you do hit a permit area operating from 8am-8pm which requires a ticket from the machine.
Cortona was a fantastic, vibrant town. With access to Rome and Florence easy by train from a neighbouring town, Cortona offers a great base location to explore southern Tuscany.
If you are planning on visiting Tuscany in the near future I’d highly recommend Cortona as a great place to stay. With views, restaurants, bars and evening entertainment in the square it makes a perfect location for your next stay.