A month in Arezzo

I could easily spend a month in Arezzo for the reasons you list. We spent 10 days in a nearby hill town, Monte San Savino --great restaurants, few tourists, which was connected to Arezzo by a commuter train spur. We were able to really enjoy ourselves because of the transportation hub in Arezzo. It's an amazingly rich city in its own right. Don't miss the monthly antiques market.

I agree that Arezzo is a good place to spend some time. We had a week there last fall and would be happy to return. However, I find that constantly making day trips begins to wear on me. I'm not sure I wouldn't select two bases for two weeks each, or four bases for one week each. We stay in apartments, and I always figure if we only stay for a week then we don't have to worry about having to launder sheets and towels and figure out how to hang them up to dry! (Lazy? Yes! I'm on vacation!) Admittedly, many wonderful spots in Tuscany don't have the easy transport options that Arezzo has, but you might look at Lucca and/or Pistoia.

I would probably also do as Janet suggests and do two weeks in two different places. Arezzo is great for one of those. (And don't forget Umbria.)

Arezzo is a great place, although I might be biased since the province of Arezzo is where my parents “emigrated” from when they settled in Florence a few years before I was born.

I say “emigrated” because my father obsessed me with his “life lectures” throughout my childhood about how difficult it was for him to “emigrate” from Arezzo’s countryside to a foreign city (Florence) a whole 40 miles away. Those lectures finally stopped when I “emigrated” from Florence to San Francisco, it was only then that my dad realized his “life story” couldn’t compete with mine any longer.

Having said that, I would also limit my stay to a couple of weeks, and spend the other half of the month in some other city, so that you can take more day trips from another location. Two weeks should be enough to see Arezzo and the many quaint towns nearby. Beyond that, the distances become a bit too far for Day trips from Arezzo.

Arezzo is a good base to visit the following (besides Arezzo itself), in alphabetical order
Anghiari
Castiglion Fiorentino
Castiglion del Lago
Cortona
Loro Ciuffenna
Lucignano
Montepulciano
Poppi & Casentino Valley
The above is only a partial list of notable places within 45 min drive. But of course even Florence is less than one hour away (many Aretini commute to Florence daily).

Useful Aretino word: Alò (let’s go! Come on!)

Thanks all. Great insights and now some things to contemplate.

And only 1 hour 14 minutes to Bologna