Tuscany Drive from Florence

Have you looked at Rick’s suggestions in his books? I try to check out one of his books from the library to review and narrow down possible destinations. Even an older copy will have basic itineraries. I also check out the appropriate Lonely Planet books.

I went through the same dilemma on our first trip. I used Rick’s book and decided we just could not do it all, so would do one area well instead of trying to cover greater Tuscany.

How many nights do you have? Where will you go after Tuscany?

With three or four nights, I’d stay in either Montalcino or Montepulciano (we chose Montalcino) and explore that area, the Val d’Orcia. One day drive between the two stopping in Pienza. Another day check out the Abbey of Sant’Antonio or maybe the Abbey of Monte Olivetti Maggiore, and so on. Take a look at the map of that area and with Rick’s book, zero in in places within a 60 or 90 minute drive that appeal to you.

Some of the plan will depend on where you go next. If on to Rome, for example, take a day to drive to Orvieto, drop the car, and spend a night in that lovely town.

I’ll throw in a suggestion for one of my favorite towns in all of Italy – Montepulciano. We have been going to Montepulciano a few times per year since 2014 and it never disappoints. This hilltop town is large enough that it has amazing restaurants, beautiful views, fantastic wine (Vino Nobile di Montepulciano), and many other wonderful qualities all while maintaining its authentic Italian charm.

From Montepulciano as a home base, you can easily explore Siena, Cortona, Pienza, Assisi, Perugia, Montalcino, etc. The list goes on and on. If you like visiting wineries, Rick Steves says Montepulciano is his favorite base to explore the Tuscan wine country. There are so many fantastic wineries in the Montepulciano area, you will have a hard time choosing!

For places to stay, I’ll suggest my two favorites. The first, Fonte Martino, is a new B&B located in the countryside, but only about 5 minutes from town (https://www.fontemartino.com/). The second, Charming Homes, is located in the historic center and has apartment rentals (https://www.charminghomemontepulciano.com). We have stayed at both and had wonderful experiences. It just depends on if you are looking for an apartment to rent or a B&B experience...

Hope this helps you a little – have fun!

Another area of Tuscany: Chianti: Siena, Radda, Castellina, Panzano, Greve. Green landscape, vineyards, beautiful. Just south of Florence on historic SR 222.

Caryn, as Laurel suggested, draw a box around the area you wish to visit. My tip is to head to the furthest location first, working your way back to your lodging. We've used this agriturismo 3 times, out of our six trips to Tuscany, we keep going back.

http://www.borgorapale.it

From here, my box goes from San Gimignano to Bango Vignoni to Montepulciano to Cortona to Anghiari. All five points are under 1:15. All the above suggested locations are within this area.
We generally do two location a day, sometimes hitting a third.

You really can't go wrong anywhere you stay, Of course you'll have to drive the Chiantigiana.

We stayed just outside Greve at the Castillo di Verrazzano. The food was wonderful. The rooms were reasonable and had a charming atmosphere. We stayed there partly because we did a day trip by bus to Florence (we'd been before).

You might also want to look at something a little more centrally located, something around Siena.

This is an excellent idea. Driving in Tuscany is easy and fun. Strictly adhere to speed limits (you'll want to go slow anyway) because they have automatic cameras. The ZTLs were well marked everywhere we went and are easily avoided. There's lots of parking outside the ZTL. We got no surprises when we got home.

And, if you've never driven in Italy, read this...

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Download their e book. Much more info there.

We stayed in an agriturismo outside of Pienza -- the upside is that we were able to easily get in/out out of it and onto the main roads without a lot of traffic (vs. the lines that back up in/out of the hill towns). The downside is that we weren't able to walk to restaurants for dinner, and wound up making some food in our little kitchen (or maybe that was an upside?). I think there's pros/cons to both and you just have to decide what's more convenient (and if you say in a hill town, make sure that wherever you're staying offers parking).

We wound up hitting a couple of towns each day, but agree that Montepulciano is a must and one of our favorites (we visited on a Sunday and were able to go through their market). We also visited Montalcino, Cortona, Siena, Sam Gimignano, Gaiole, Civita de Bagnoreggio and Orvieto (some we visited on our way down from Florence or from Tuscany into Rome). Civita is really interesting, if you want to feel like you've stepped back in time, for it's only accessible through a pedestrian bridge and they've done very little to update the exteriors once you're over there. The Crete Senese drive (in RS book) is also beautiful and we visited the Abbey of Monte Oliveto Maggiore along the way (the monks sell olive oil and wine -- and they were pretty good!).