3-4 days in Tuscany in the middle of a 12 day trip


New member
First time to Italy and I could really use some help with logistics for our upcoming trip! 3 of us going for 12 days. We are flying in and out of Rome and plan to do the first half of the trip via trains. Rome for 3 nights, Florence for 3 nights and then we would like to spend 3 nights in a central location in Tuscany and travel by car to various hill towns before returning to Rome for 2 nights before we fly home. The list of towns on our short list are: San Gimignano, Volterra, Siena, Montalcino, Montepulciano and Cortona. The biggest question is how to handle logistics.
1. Is that too ambitious for 3 days?
2. If not, how do we pull it off with a car? I understand that Siena is not the best place to have a car and out of all the locations I listed that is probably the lowest priority, so should we check that off the list?
3. Where is the best place to stay if we want something in between busy town/remote farm?

So excited but I want to make sure we make the best use of our time!


Well-known member
You plan isn't too ambitious to me.
If you plan to hire a car, you won't have any problem in moving from a location to another.
All the places you've listed are not so distant, I think you'd better start your journey from San Gimignano and move then to South, direction Volterra, Siena, Montalcino, Montepulciano and finally Cortona (which I think it's the one that less belongs to this itinerary, but it's a marvellous town to visit anyway).
You could spend the first day visiting San Gimignano and Volterra and book an accommodation there or move towards Siena and find a lodging in or out the city, you'll obviously have more choice in Siena and its surrounding among farmhouses, hotels, vacation homes and B&B.

The second day could be dedicated to Siena. Out of the old city center, you won't have any problem in finding a car park (fee always required, rates are anyway calculated on daily or hour basis and aren't too expensive).

Before the end of the day, I suggest you move to Val d'Orcia to find an accommodation and start from there to explore all the area (marvellous landscape) and drive to Montalcino, Montepulciano and Cortona. Last night there.

If you prefer instead loding all the three days in the same place, then Siena is the most central location you've listed for moving to around the other towns. You could find an accommodation in its surroundings if you don't want to stay in the busy town (Siena is, however, much less chaotic then Florence or Rome).