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Exploring The Back Streets Of Tuscan Hill Towns.

Updated: Mar 23, 2023

One of our favorite things to do on a spring afternoon is drive the back roads around Montalcino. If we see a little town up on a hill off the main road we make a beeline. Invariably every hill town is beautifully kept and there's usually at least one local restaurant where you'll usually find a tasty lunch.

Not far from Montalcino (about a 20 minute drive) is one of our favorite towns. It's called Monticchiello and it is absolutely charming. One of our favorite walks involves parking in nearby Pienza and making to 1.5 hour walk on gravel roads to Monticchiello. The view from the old town wall of Val d'Orcia is one of the best there is and you can even see Montalcino.

Doorway in Monticchiello, Italy
A typical, lovingly-kept doorway along one of the back streets in Monticchiello about 20 minutes drive from the Villa. I love the exquisite light in the back streets.

Now the second ingredient to any really great walk is a great lunch spot. In Montecchiello there is Ristorante La Porta. Make a reservation because their small outdoor patio atop the walls is a lunch you'll remember forever and the tables are in high demand. The menu is absolutely wonderful and their selection of Vino Nobile di Montepulciano is as good as you'll find. The restaurant will call you a taxi to take you back to Pienza but we prefer to walk and reward ourselves with a gelato back in Pienza. Our favorite is a tiny shop on one of Penza's beautiful back streets. It's call Buon Gusto Gelateria. Don't miss it. You can also watch the sunset from Idyllic bar below the Pope's palace. Another "Don't Miss It" tip.


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