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Hilltop town itinerary - Cortona or Arezzo?

I have been checking out some options for visiting the hilltop towns in Tuscany. We will be coming from Venice, and plan to take the train and/or busses. Here is what I was thinking:
6/21 Travel from Venice to Volterra, spend 2 nights
6/23 Travel from Volterra to either Cortona or Arezzo, spend 2 nights
6/25 Travel to Florence in the evening, spend 1 night
6/26 Morning flight
My questions are:
1. Is it best to take the bus to Volterra from Florence, or is there a better option? Is there a site with the bus schedules in English? Do you buy bus tickets on the day of travel, or reserve ahead?
2. Any opinions of Cortona versus Arezzo? We are looking for a less touristy place to relax, drink the local wine, do some low key sights.
3. Lodging suggestions for these towns?

Posted by
15260 posts

Two choices:
1-Bus from Florence to Colle Val D'Elsa then change to bus to. Olterra.
2-Train to Pontedera, then bus to Volterra
Bus websites are likely all in Italian. But you are lucky. You don't need to learn Roman numerals. The numbers are the same in Italian.
You can buy tickets in board or bus station. No need to Reserve in advance.

Posted by
11613 posts

I think Arezzo is much more interesting than Cortona.

Posted by
15260 posts

In your shoes I would stay in Arezzo for the two nights. More to do and see. Arezzo is a short train ride from Florence (45 min). Lots of people commute from Arezzo to Florence every day (Arezzo is cheaper to live in).
However Cortona is a short bus ride from Arezzo, therefore you can easily visit also Cortona while in Arezzo.
The other question is: do you need to stay in Volterra two nights? You don't even plan to rent a car to see things around there. Without a car I would stay in Florence or Siena and visit it from there.
If you don't intend to drive, you should stay in provincial or regional capital cities (Arezzo, Siena, Florence), not in small villages. You need a car for that.