Our tour ends in Rome and then we’re looking for a place to stay for four nights on the way to Milan. Would like to be not very touristy, easy to walk to food and wine. Thinking about going to Cortona, it looks quite nice, historic, small but large enough. We’ll be there in May, have a car, so we’ll be taking day trips. Mostly want a nice place to stay, easy walking to food and wine in the evening. Any thoughts, recommendations?
Month of year? Car rental or not? Wine vs Art vs Shopping vs hiking? Is Milan just for the flight home? Hill-climbing abilities? Pool? Air-conditioning?
Tuscany has many pretty towns to wake up in. Only a few have more than a day’s attractions. I liked Cortona a lot, but we didn’t sleep there, and we had a car to get up the hill. Few towns have walkable wineries, as opposed to wine tasting bars. We didn’t eat in Cortona because we had a prepaid reservation for lunch at a driving winery, Avignonesi.
Cortona is quite small and lacks attractions other than the atmosphere of the historic center, in my opinion. Worse, 'Under the Tuscan Sun' still casts its tourist-heavy shadow. How about Modena, a gentle beautiful town with easy side trips to Parma and Bologna?
We love to stay in Lucca and it makes a nice base.
Interesting cities along the way:
Arezzo
Florence
Bologna
Modena
Parma
You can easily visit Cortona from Arezzo..
We've been to all the places on Roberto's list and also to Cortona. I would choose Arezzo, as it appears you might be interested in a smaller place than Florence, Bologna, etc. Arezzo is larger than Cortona but not as large as the others. You'd have a better selection of restaurants and so forth in Arezzo than in Cortona - and in my opinion it's less touristy than Cortona. We stayed five nights in Arezzo and really enjoyed it.