I'm planning my upcoming trip to Italy in October and I have most of the itinerary planned except for Tuscany. We will be renting a car on our way out of Florence and would like to stay two nights somewhere in Tuscany and then head to Cinque Terre. I have been to San Gimignano so I'm looking for somewhere new and probably a small town since we will be coming from Florence(and Venice before that). Any suggestions would be helpful. Thanks.

Here are some good options. I prefer the area south of Siena. Have fun !

BOB’S FAVORITE DIGS IN TUSCANY

Siena province is easily my favorite part of Tuscany. Here is a list of accommodations that I suggest. All prices assume a typical double room.

A. RURAL LOCATIONS: All have parking and good food options nearby

1. Relais La Saracina www.lasaracina.it 230 to 300E
Fabulous country home near Montepulciano—helpful owners

2. Le Traverse www.letraverse.it 155E
Small B&B just south of Pienza—hard to beat at the price—has pool

3. Lucignanello Bandini www.piccolomini.it 150[2] to 244E[4]
These are apartments in a lovely but remote rural setting.

4. Hotel Pescille www.pescille.it Good value at a rustic hotel only 3 km from famed San Gimignano with great views---100 to 130E

5. Fattoria Tregole www.fattoria-tregole.com 110E to 180E
Has both B&B and apartment accommodations. Near Castellina in Chianti


B. IN-TOWN LOCATIONS: For walking convenience to shops etc.

1. Palazzo del Capitano www.palazzodelcapitano.com 130 to 180E
Very nice small hotel in center of San Quirico—perfect location to explore.

2. Vecchia Oliviera www.tuscany.net/oliviera/ 130 to 180E
Nice 4 star hotel at the gate into lovely Montalcino---has pool.

3. Palazzina Cesari www.montalcinoitaly.com 80 to 110E
Lovely small B&B in heart of Montalcino—great value—2 nite stay minimum.

4. Locanda di San Francesco www.locandasanfrancesco.it 180 to 200E
New boutique B&B in a lovely location in Montepulciano—great reviews !

5. Palazzo Ravizza www.palazzoravizza.it 130 to 180E
Very nice & popular hotel in Siena with parking.

Thanks Bob! I appreciate all the suggestions. Any idea how long it takes to drive from Florence to Pienza/Montelpulciano area (ballpark)?

I'm in Montepulciano right now-sunny and will be 68 degrees. Driving time between Florence and here is one hour forty five-give or take 15 minutes. There's a lot to see if you want to stop or go less fast routes.
You might also consider Lucca for your stay prior to CT.
Buon viaggi--Paul

I loved Monteriggioni, too.

If you can have a look there, it has something magic! ;-)

http://www.summerinitaly.com/guide/monteriggioni

Less than 2 hours, but I would stop at the Abbey at Mt. Oliveto Maggiore enroute and drive through the Crete region from Asciano. The Fattoria Tregole is only about an hour south of Florence and in the heart of Chianti.

We did the opposite last summer. We went to Volterra, which we loved. One of the highest points in Tuscany and a fabulous little walled city at the top. Its a bit more to the west so actually seems closer to your final destination....

Thanks everyone! I think we will head to Pienza/Montepulciano/Montalcino since we have already visited Volterra and San Gimignano. If you have recommendations of places to stop on the way down from Florence or places to eat/sleep in those areas please let me know.

A great place to stay, just outside of Pienza, surrounded by the most beautiful landscape and hosted by warm and friendly people-

http://fontebertusi.it

You cannot go wrong in southern Tuscany.

Another little town in southern Tuscany which may be worth a visit is Chiusi.

If you are interested, you may see some video of Chiusi and Montalcino on our website, www.WebVisionItaly.com.