Tuscany by car

Hi there,

Myself and my partner are planning a trip to Italy in October this year and were looking at your two week plan – but doing it in reverse, so starting in Rome, finishing in Venice.
I was just wondering where you would recommend staying in Tuscany? We would be hiring a car in Rome and driving up towards Florence, so we are looking for a good base to explore Tuscan countryside, before moving on to Florence.
We actually have 18 days in total, but as the schedule is quite busy, we thought we would just spread things out a bit -and also perhaps visit Bologna on our way from Florence to Venice.
I was also wondering if you would recommend pre-booking all our trains etc? Or would we be ok at that time of year to find things when we arrive?



Hi Coral.

Since you plan to arrive from Rome, you could stop in Pienza, 2,5 hours driving from Rome. Pienza is a wonderful renaissance small town and an excellent base to explore southern Tuscany (Pienza itself, Montepulciano, Bagno Vignoni, Montalcino, Siena – not all of  them, I regret you’ll have to make painful choices!). On your way up to Florence you can stop in San Gimignano or in Chianti (Castellina and Greve, with its fantastic Wine Shop).
We could fine tune depending on your tastes and aspirations (art? food? romance? landscapes?)
High speed trains may be very busy, especially during WE. You could actually prebook (aso in order to get better tariffs) and change your tickets in case of need by paying the difference to the full tariff. Check www.trenitalia.com (state owned) and private compettor www.italotreno.it. Regular trains (the ones to go to Lucca, Pisa, Cinque Terre, …) are usually OK, except during WE.
By the way: don’t hire your car while you’re in Rome, you are notallowed to drive private cars in the city center during week days – and driving there is a mess, anyway!
Hope this helps. Feel free to come back to me for more info.
Hi JP,

Thank you so much for the wonderful advice!
Just a quick question – where would you suggest we pick up the hire car if not in Rome?
We are big foodies and also lovers of landscapes so to be honest seeing anywhere is a treat for us!
We are really looking to have a more relaxing time driving around Tuscany, sampling food/wine and nice views.
Sorry also just checking what you mean when you say during WE?
Thanks again,
Hi Coral,

I’m glad you find my mail useful.
If you don’t want to hire a car in Rome, then you can visit Rome, catch a train to Orvieto (which is close to Pienza and Montepulciano, and worth visiting, anyway) and start your Tuscany exploration from there. If you are looking for good food and stunning landscapes you will be in the right place, and I confirm the destinations I mentioned in my previous mail. You could also rent a car in Florence, but it makes less sense from a logistics point of view and, just like Rome, you won’t be allowed with your car in the city center.
By “WE” I was just referring to “week ends” – you are likely to find crowded trains and traffic jams on Friday evenings, Saturday mornings and Sunday afternoon/evenings (like in any other western country, obviously).
Enjoy planning your trip!

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