Driving from Florence to Montepulciano

Our favorite Tuscan hill town is Montalcino; which is the home of Brunello. You can visit the fortress and eat lunch in several restaurants with a breathtaking view. The lunch tasting menu at Castello Banfi is absolutely amazing, but you will need a couple of hours for that. (And a nap afterwards). The best view is at the Enoteca Di la Piazza. http://www.enotecadipiazza.com/en/ You can taste wine here also and find out what you like. AND......these guys will ship to your home for free so you don't have to carry it home.

Buonconvento is also a good stop. But Montepulciano itself also has so much to offer, so don't shortchange yourself time there.

I didn't find Pienza to be so big or touristy as you might think. It's one of the most lovely of the small towns.

That said, my favorite small Tuscan town I visited that was off the beaten path was Bagno Vignoni. In addition, the abbey of Sant'Antimo is nearby and is definitely worth a stop.

Marsha,
You've posted the same question twice.
You may consider deleting one of your duplicate posts so you can keep all your replies in one.

You don't have the option of the big towns, because it takes half an hour to park and get into the center of town from the parking. I don't think the tiny towns are as important as you do, because all of them are "ready for tourism". Some, like Monteriggioni are unique in some way, but others, like Sant'Angelo in Colle are only a memory of medieval times.

According to Google Maps, you have an easterly and a westerly route to choose between, and you better allow 2 hours plus on the road. My suggestion is to focus on one intermediate-sized town and eat while there. (Note that you don't have time for a gourmet Italian lunch on your driving schedule. You need a restaurant with experience serving hasty tourists.) I don't put Pienza in the same class as Siena and San G, of bloated-tourism. But you could also consider Cortona, because it has a compact art museum with a few important works, and a pretty hill-town feel. Montefollonico is also attractive, but I just see it as too small for the "overhead" of stopping. You'll find the same cheeses for sale in all the towns, just follow your nose.

We did the exact same itinerary two years ago. We had a wonderful road trip, but it took us about 4-5 hours with a lunch stop (and getting happily lost - you will!). A local resident gave us the route. Even though we had a Michelin map, it was not as helpful as that route given to us on TA. The reason is that Italian road signs do not indicate route numbers with any consistency, so you end up following town directional signs instead, through all those roundabouts. Can't tell you how many we went round more than once looking for "our" next town. Breathtaking scenery.

We stopped at a hilltop town for what was one of the best lunches on our whole trip, Bar Ucci in Radda. Took about an hour but we did not have a tour to meet. We did arrive in Montepulciano in mid afternoon, I believe we picked up the car a bit later than you are planning, so it seems you have the time to stop for lunch.

Here is the thread: Take note of response number 5. It is exactly the route we took, and the town names were invaluable:

https://www.tripadvisor.com/ShowTopic-g187893-i67-k7636699-Navigating_in_Tuscany-Tuscany.html

Hope this helps!

Thank you, Joan. I copied and printed your thread, that should be very helpful.