Best base for driving in Tuscany

dan cleary

New member
Hello, and I am pleased to join such a friendly forum! My wife (who is 5 months pregnant) and I are flying into Pisa on Wednesday 8th August for 2 weeks. We are renting a car. We have the following questions; would you recommend more than one base to explore Tuscany? These are the places we would like to visit: Pisa, (we are currently booked in Pisa for 4 night), Siena, Chianti, Florence, Prato, Pistoia, Volterra, San Gimignano, maybe even a day trip to Rome. Are we missing any other "must see" places"?

Thank you for your help and tips! :)

Dan and Debbie


The Tuscan Expert ;-)
Staff member
2-3 bases would work best to see the top must sees in Tuscany

Ciao Dan and welcome to our Forum! Congrats to your wife on the pregnancy and definitely listen to her needs for deciding how long to stay in one place - since I'm also currently expecting, I know sometimes an extra day and taking things slower can make a big difference in the enjoyment of what you're visiting! ;)

From Pisa, you can certainly take the time to explore both Pisa and the surrounding area - I'd recommend heading to Lucca and to the seacoast from Tirrenia and down for day trips. You can see some of the top beaches here.
I suggest the coast because it is currently really really warm all over Italy (don't want to say hot but there is an extraordinary heat wave coming up from the Sahara desert that is supposed to last until Wednesday, then it is supposed to get better). So the coast might be perfect for those first few days!

Then from there, I'd suggest heading towards the Chianti area to use as a base. Chianti is more central than Florence, and with a car I'd recommend avoiding the city center in particular. From there you can visit both Florence, Chianti and Siena - as well as San Gimignano, Volterra, and the towns near Florence.... so I'd recommend you look today and tomorrow at a place you can stay at in Chianti for at least a week. A farmhouse or villa apartment would be perfect - take a look at the offerings on this page and contact them to ask for availability.
These types of accommodations don't usually offer online booking and it's difficult to know whether they have availability once you're in the area other than by phone (there are no signs outside saying they have rooms, and driving around in search would be no fun).
Generally August is the high season and everything gets booked ahead of time, but this year with the general crisis we've heard numbers of visitors are down and you might get lucky really quick. So I do recommend you don't wait and start contacting several of them right away and hopefully you'll have something set up by the time you are ready to leave Pisa.

From Chianti and for your remaining days (assuming you fly back out of Pisa, right, so planning to stay in Tuscany the whole time?), I'd suggest you move down a bit to the Val d'Orcia area or near Arezzo. This places you in southern Tuscany from which you can do day trips to the small towns of Montalcino, San Quirico in Val d'Orcia, Pienza, Montepulciano, Cortona, Arezzo... there are so many possibilities in that area, I highly recommend you take the time to go around the area. Take a look at accommodation in that area here and here (mmm, I see that Agriturismo Incrociata actually has online booking, you could check that out for both the period in Chianti and southern Tuscany since it is pretty central for both).

While Rome doesn't seem far from Tuscany, I wouldn't suggest a day trip. If you've never been, Rome has so much to offer you cannot pack it into a day trip - you need at least 2-3 days there. If you want to include it is this trip, then plan to go down there for your last few days (but if you're flying out of Pisa plan to come back to Pisa at least the day before) to really enjoy it. Otherwise, maybe for a future trip? Tuscany has lots to offer so you won't find it difficult to fill your days, as you can tell by the suggestions of what you can see that I've given. Here is just a basic 7 day itinerary in Tuscany that highlights some of the top must-sees (there are many more and given you have more time, you'll have a chance to see many more of them).

Definitely keep your wife's condition in mind and remember that Tuscany - and all of Italy for that matter - might look small on a map but has so much history, art, culture and food and wines to offer, that it is best enjoyed calmly and slowly. There is so much to see and absorb per square kilometer that it takes time to see things as well as move between places.

Let me know if you have any other questions or doubts I can help clear up - and have a great vacation!! :D