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Driving and exploring the Tuscan Hill towns

We are beginning in Florence for 3 days and then picking up a car and want to take a leisurely drive to Montepulciano where we will stay for 3 nights and then head to Siena for two nights and then back to Florence. Some places we would like to spend some time include San Gimignano, Antinori Winery and briefly drive through the American cemetery. While in Montepulciano we would like to perhaps hire a driver to take us to some wineries for the day, even though we will have a car, so my husband can enjoy more than one glass. I am looking for some suggestions on both day trips from Montepulciano and on the best drive from Florence to Montepulciano. Thank you.

Posted by
907 posts

Some thoughts

A leisurely drive to Montepulciano could, and probably should, take you right be Siena. So, leave early, spend the day in Siena, then on to your lodging in Montepuciano. That could save you some time. If you like Siena, great go back and spend two days, if not use the time elsewhere. Just take the SiFi autostrada and you go buy a lot of places such as San Gimingnano, Certaldo, and Monteriggioni and into Siena.

From Montepulciano a nice place to visit is Pienza. Check it out. Montalcino (Brunello) is close by as well. Those two towns are basically on the same route.

Posted by
792 posts

I applaud your decision to leave the car behind while you enjoy the wineries. I have a car in Tuscany but am the "designated driver" and taste, but never have a glass before driving those twisty roads. BUT, I do buy a few bottles and enjoy them when I get back to my base.

Posted by
99 posts

Thank you for for the advice of seeing Siena first for a taste of it. I wouldn’t have thought of doing that since we plan on our last two nights there but I think it makes sense for the reasons you mentioned.

Posted by
9039 posts

Siena is a great night town. I would not do two visits. There are so many other towns you could visit briefly on your way and then finish with those two nights in Siena. Siena well repays a full day and being there for the evening is lovely. Montepulciano is also a great base as it is both picturesque and has lots of good restaurants within a walk in the evening. As you are aware, you can't drink and drive, so having a town with lots of walkable bars and restaurants is perfect.