Driving from Florence to Chianti, Siena and further South


New member
Hi, my husband and I are going to be in Tuscany for 5 days this September. We are planning to spend 2 nights in Florence and then hire a car and self drive to other tuscan towns. After reading a few posts on the net I got a general sense that driving around in southern Siena (Pienza, montepulciano, monticiano..) is easy going, but I would like to know about the drive from Florence to Chianti and Chianti to Siena. Could we get some advice on this keeping in mind that we are not used to left hand driving. Are the roads too busy?

Considering we have only 3 days, we thought the best way to see the country side would be to drive down. Start from florence, stay the night in Chianti. Next day look around San Gimignano & Montgomery and reach Seina and stay the night there. Third day we head to Pienza, montepulciano, monticiano.. and stay the night at Montepulcino.

Can we return the car in Siena? do car companies offer such options?

It would be very helpful to get some advice on this. Been struggling with this part of our travel.


Well-known member
Driving around


You can save yourself a lot of hassel by simply returning the car to Florence, especially if you are going back to the airport (catch the train from Florence). I suggest that you invert your calendar and start with Montepulciano. You can catch the autostrada to Montepulciano, and start working your way up from there.

Montepulciano, Pienza and maybe look into a B&B at Bagno Vignoni

Montalcino, Buonconvento, a vineyard (I suggest you look into Altesino between Montalcino and Buonconvento - historic cantina, beatutiful views. I have been here and they have a nice tour of the cantina
or Castelnuovo Tancredi - the last time I was here, the person who did the tour was quite the character (fun type!) The farm is truly amazing.
Stay the night in Siena

then Montereggioni, San Gimignano (Vineyards are always fun, try Pietrafitta, Chianti

back into Florence.

I know this puts a somewhat un-conventional start to your trip, but I think it will maximize your time and make your drop off easier and more cost effective.

Buon Viaggio