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!

Montepulciano medieval towns in Italy

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.

family holidays in tuscany

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.

the best views in montepulciano

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.

planning a family trip to italy

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.

things to do in montepulciano 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.

where to eat in montepulciano italy

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.

things to do in montepulciano

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.

montepulciano italy travel

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

things to see in montepulciano italy

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

tuscan sunset in montepulciano

where to eat in montepulciano

italy with kids

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.

gelato in montepulciano

montepulciano tuscany italy

montepulciano italy tuscany villages

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.

If you’re heading to other places in Europe, here are some more posts you don’t want to miss!  You can check out our entire Europe Travel Gallery to see all of our posts and helpful info.

Things to See in Europe

Tea at the Orangery | Riding Trains in Europe | Dublin Travel Guide | Paris Museum Pass | Best Family Hotel in Rome

Things to do in Europe

Visiting Bruges | Staying Connected in Europe | Best View in Paris | Amsterdam Canal House | Borough Market

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Happy Travels!



Creative Director at Pink Peppermint Design
Tammy Mitchell is the founder and creative director of lifestyle blog Along with being a homeschooling mom of two kiddos, she is also an in-demand prop and event stylist, photographer, interior and graphic designer. On Pink Peppermint Design, she shares creative DIY projects, easy entertaining and gift ideas, inspiring interiors and events. She lives in Southern California, with her husband and two children.

Best hilltop towns in italy montepulciano

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