Would it be feasible to stay in one place like around Montalcino or Orvieto and do day trips to the other towns? Would it be better to stay in 2 or 3 places?

Well, I hope you have a good map. Orvieto is not in Tuscany and is way too far south for a base location. Montalcino is good for south Tuscany. Read a good guide book or two and decide which places you most want to see.Then, put pins in the map. Pick your location based on a 50 mile radius of the most pins. Given 2 weeks, I would stay in 2 locations--one south and another closer to Florence. Good luck !

Hi rev,

Good advice from Bob.


How long do you have?

We probably have about a week or maybe slightly more. We plan on doing the small towns of Tuscany/Umbria since we figured could do the bigger towns on another trip using the train. I wanted to kind of take it easy and not have to rush around. Any thoughts on San Gimignano and Volterra (really liked by Rick Steves) vs Chianti region. Might be a little rushed to try to do both. (?)
Probably stay 3-4 nights in the south around Montalcino area and 3-4 in north in San Gim. or Chiati area. I have heard the San Gim. is really heavily over run with tourists. We are going in June to attend a wedding at Lago d'Orta and driving south to leave from Rome.
Thank you for your advice.

Hi Rev,

On my second trip, we stayed in Chianti for 4 nights in a tiny village and drove from there to San Gimignano, Volterra, Siena, Greve, Castellina, lunch to La Badia di Coltibuono, Castello di Brolio. We loved our small inn and the little village of San Sano, but it was a lot of driving over the narrow, windy roads of Chianti.

I would recommend staying in Chianti - if you are mainly going there for lots of wine tasting and relaxing. If you are thinking of using it as a base to drive to SG and Volterra - it's a long drive. San Sano is very close to Siena, 20 minutes drive north.

I would recommend staying in Montalcino/Pienza/Montepulciano area for southern Tuscany and I think staying in SG for further north is an OK idea. If you are using SG as a base, you will be gone during the day when it's crowded and coming back in the evening when most have left. Sounds like a great strategy to me.

I loved SG and thought it was one of the most beautiful. We were just there early in morning until lunch, then left when it got too busy.

You could do a driving day trip to Chianti if you really want to.

Buon viaggio!

We based in Siena and found the town had lots to offer at night. We drove as far as Voltarra, San Gimi, Chianti and Montalcino on day drips comfortably over several days.

On one of our trips, we stayed 3 nights in San Gimignano and 3 nights in southern Tuscany (Pienza, Montalpulciano areas). It was perfect for us. We loved San Gimignano and didn't find it to be any different than Siena, Florence, Cortona, Assisi with regards to numbers of tourists. We stayed at L'Antico Pozzo in San Gimignano - loved it! Daytripped to Greve one day and stopped at 2 wineries. We've stayed at 2 different places in southern Tuscany (on difference trips) which we highly recommend - Locanda dell Amorosa (very romantic and one of the most beautiful places I've ever stayed) and La Saracina (also very romantic - smaller with 6 rooms with a charming hostess/owner). HOpe this helps!

revstj,
Bob gave you excellent advice. Tuscany is too large to see from one location. For ideas on day trips e-mail me.

Henry