Best city in Tuscany to stay for 4 days?

Question

Going to Tuscany in September for 10 days. We don't want to unpack and pack too many times, so here's a possible itinerary:

- 3 nights in Florence (hotel)

- 4 nights in Tuscan town (villa or farmhouse)

- 3 nights in Rome (hotel)

What's the best city in Tuscany to stay in that gives a true Tuscan experience (w/ good food and wine) and is in a great location to do day trips?

And if you can't pick one, what are the top two? Thanks.

Answer 1

Pienza is my favorite little Tuscan town and would be a great place to stay. My question is, will you have a car? If not, getting to and from Pienza will not be easy. With a car however, you could easily visit the following places from Pienza:

Montepulciano, Montalcino, Siena, Cortona, the abbey of Monte Oliveto.

If you are looking for a place that is a little more easily accessible by public transportation, check out the Arezzo/Cortona area.

Also a good bet but not between Florence and Rome is the Lucca area.

Let me know if you need more help finding places to stay. I've lived in Italy for 10 years and have worked in tourism.

Answer 2

Can I suggest you Pienza ....

http://www.pienza.net/

Answer 3

I agree with Pienza if you have a car, but for public transportation the best city in my opinion is Siena.  There are day buses from Siena to San Gimignano, Montalcino, Montepulciano, etc., so you can spend the daytime away from Siena, yet there is plenty to do in the evening.  

You can then take a train, or a bus, from Siena to Rome.