Favorite Tuscan Hill Town
 

My husband and I will be in Tuscany for three days in May. Our time is limited so I need some can't miss suggestions. What are your favorite spots in Tuscany?

I'm sure you'll get other better-known ones. I'll suggest Monticchiello.

I suspect you'll get a ton of replies on this, each with different favorites.

I'll jump in with a few faves of my wife and me:

1. Montepulciano--hands-down our favorite. Smaller size, nice shops and restaurants, quite relaxing. In southern Tuscany, good for day trips to Montalcino and Cortona (both worthwhile stops).
2. Siena--Piazza del Campo is crowded with tourists, but still work a visit. (Note, this is larger town, but the historic centre is doable in a day or two)
3. San Gimignano--ditto on the tourists, but still worth a visit
4. Pienza--take an hour or two to check out the Renaissance-gem square
5. Cortona--others may disagree, but I think this is good just for a day trip.

While this list has some touristy places on it, there's a reason--they're really worth it. No matter how many tour buses pull up to San Gimignano, it's still pretty cool to see. One of the keys to enjoying towns likes this is to stay overnight. In the evening, after most of the hordes have left, these places are much more serene and enjoyable.

Three days will certainly whet your appetite for more of Tuscany... Enjoy.

I've been to San G., Montalcino, Volterra, and Siena and my favorite was Montalcino. It may have had something to do with the Brunello, though...

It is amazing how many people love Tuscany. We are staying in Montepulciano on our way back to Rome but I am looking for a stopover choice somewhere more northern for our first night. We want to see San G. and Siena during those two days. Any suggestions?

It's nice to stay in San Gimignano. Then you're there when the tourist crowds depart. We stayed one night at the Belsoggiorno and had a room off the first floor terrace overlooking the Tuscan countryside. We stayed on the terrace until late afternoon.

Ditto on San Gimignano as an overnight stop. Walking out of Hotel La Cisterna, into the quiet and empty piazza,(after tourist buses had left ) and seeing the towers silhouetted against the evening sky was magical.