Itinerary Near Tuscany

I enjoyed Castellina in Chianti which is driving distance from Sienna. There are multiple good restaurants to try there.

Certaldo, San Gimignano and Volterra are where we visited. We shopped at modern grocery stores in Poggibonsi--north of Sienna. There are a number of other hill towns in the region. Tuscany is known for quality wines including some of the best red wines anywhere out of Montelcino. Beer is available, but breweries are elsewhere. Your agriturismo host can suggest restaurants for you to visit.

Besides Siena, which is a small city, rather than a town or village, some of the most visited towns in the area are:
San Gimignano
Chianti hills villages (Greve, Castellina, Panzano, etc.)
Volterra
Pienza
Monteriggioni
Montepulciano
Montalcino
But there are many more.
Check here:

http://www.borghiditoscana.net/en/category/villages-en/

If you're still coming from Lighria, rent your car in La Spezia. From there you could visit Volterra and San Gimignano. Or Lucca on your way to Siena. On your other day trips, always go to your farthest location, working your way back to your lodging. Most days you can hit 2 hill towns comfortably.

An easy day trip with three locations on your way to Florence would be Radda, Panzano and Greve. Have a late afternoon lunch here.

http://www.verrazzano.com/en/wine-tours/

Another day trip could include Montepulciano and Montalcino.

Monteriggioni and Castellina combine well.

We print out maps using Via Michelin along with GPS.

Peruse the site Roberto gave and decide your own list of must sees. I don't think you can go wrong anywhere.

Breweries and beer aren't what springs to mind when one thinks of Florence. But if you Google breweries in Firenze, there are some interesting results.

We stayed in an agriturismo about 15 mins S.E. of Sienna in early July.... absolutely beautiful. It's hard to chose a place you will not like. We enjoyed following R.S. recommended "drives" and then added in a few of our own small towns. The heart of Tuscany drive was great: Montepulciano is a must see. If you go try lunch at Ristorante Deli Archi. The location and decor of the place is amazing, but the food is to die for. The owner was delightful and sang to us after we ordered our meal. What an experience.
On The way to Montepulciano we stopped off at Truquanda - another quaint hill town - enjoyed it.

We also enjoyed the R.S. Crete Senesi drive. The Abbey Monte Oliveto Maggiore was fascinating (If you go keep in mind the abbey is closed between noon-1530). Buonconvento only a 10-15 minute drive from the abbey and was very enjoyable. It was off the tourist map and had a great feel to it.
My favorite restaurant here is Ristorante Roma da Riccardo The best pasta and gnocchi we have ever tasted.

Lots of choices here......Have fun !!!

Bill T

Thank you so much to ALL Rick Steve friends! Your advices and suggestions are so helpful!

Glad you're staying near Siena - you'll love it, particularly after dark! If your agristurismo offers dinner for an additional fee, I would definitely take them up on that! If you go to Montalcino, I would highly recommend having some wine with some small plates (crostini) in the fort at the top of town. That was very memorable! Volterra is quite charming, but it is a bit of a hike, so that is one I would cut, if you have to. San Gimignano and Montelpuciano are not to be missed.

Keep a light on for microbreweries - I was astounded at how fast my microbrewer cousin ferreted out the good breweries in Verona. Microbreweries are getting more and more popular. Keep asking around and checking on-line!

Aside from the usual suspects of:
San Gimignano
Chianti hills villages (Greve, Castellina, Panzano, etc.)
Volterra
Pienza
Monteriggioni
Montepulciano
Montalcino

You might try:
Vinci (north a ways, about 60 miles and a cute Leonardo Museo)
Porto San Stefano (on the coast 75 miles south)
Piombino (abut 75 miles on the coast)
As mentioned, Panzano
Montecatini Terme and Montecatini Alto
Cortona
Perugia
Orvieto
Montefalco
Assisi