Medieval Towns in Italy : Montepulciano Tuscany

If you are really looking for the ultimate Italian experience, you must visit Tuscany.  This rural and beautiful region is full of rolling hills dotted with stunning, living medieval towns.  When we traveled to Europe for our three month excursion, we knew one thing we really wanted was the quintessential Italian experience…to stay in a Tuscan Villa in the beautiful countryside and spend our days wandering from medieval town to medieval town, eating local cuisine and enjoying the sunshine.  There are SO many beautiful medieval towns in Italy, you can spend a month it seems traveling from village to village, so I will highlight a few of our favorites.  Montepulciano is definitely one of them! If you are wondering about the best hilltop towns in Italy, Montepulciano is a great place to start!

After a busy week spent in tourist hot spot Rome, it was an incredible experience to pick up a car and shift our hectic travel schedule to a more peaceful pace.

With temperatures in the 100’s we spent the earlier part of our days laying by the pool nestled in the olive groves, and then set out in the later afternoon to wander the winding scenic streets of medieval towns.

Montepulciano is perched roughly 2000 feet above sea level, and offers stunning views of the countryside below.  Much of the architecture that exists has been in existence since the mid 1500’s.

It is truly incredible to wander the same streets of medieval towns in Italy that people walked over 500 years ago.  As a matter of fact, Montepulciano has one of the most intact historic city centers of any town in Italy.

Part of the charm of visiting Montepulciano is that it is much less busy than other historic towns like Siena and Cortona.  Yes, it gets it’s fair share of tourists, but it is a little more off the beaten path, therefore not as crowded.  Because we were there in August, when Italians usually vacation, it was quite quiet.

Visiting in the late afternoon and evening is another secret to enjoying a quieter and more “slice of life” experience, which is our favorite way to travel.

In the evening most of the tourists have left these medieval towns and so instead of fighting crowds of tourists, you can spend your time chatting with locals and feeling, even if for a minute, like you are one of them.

Did I mention that the views from Montepulciano are stunning? 😉

We had the pleasure of dining al fresco at a beautiful little restaurant Osteria Del Borgo on the terrace with a beautiful sunset backdrop.

No matter how full you are from dinner, there is always room for gelato.  Every medieval town has at least one, if not several, gelato shops.  Montepulciano is no exception.

If you are planning a trip to Italy, especially Tuscany, make sure to include a visit to some of the medieval towns in Italy and be sure to put Montepulciano on your list.

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Happy Travels!

Tammy