Tuscany draws people to it every year in droves. From the rolling tuscan countryside, tall cypress trees, olive groves and stunning sunsets. It’s not surprising that this area is so popular and its appeal never ceases.

We all know about the main best places to visit, Florence, San Gimignano and Pisa. However, here at Mammaprada we love to highlight the lesser known small towns which are just as incredible and often even more so. 

Italy is a country full to the brim of these spots. While you may still want to be able to visit Florence; discovering somewhere new such as medieval hilltop towns is also a marvel and will create lasting memories. These are the most beautiful places that Italians know well but don’t shout about them. 

The benefits of these are also that they are not overly busy. Restaurants are less frantic compared with major cities and so your experience will be more enchanting. 

So let’s get inspired for your next trip. Here are the places to uncover for your next Italian Villa holiday. 

Arezzo

Close to Florence but not on the tourist trail is the pretty city of Arezzo. With ancient origins, even older than Alexandria in Egypt, Arezzo was one of the major Etruscan towns and became a Roman center of strategic importance.

Today it's a wonderful place to visit for its famous Basilica of San Francesco. The Medici Fortress, built by Cosimo I, the Palazzo della Fraternita dei Laici and the Pieve di Santa Maria. In the medieval city center you can also visit the remains of the Roman amphitheatre. 

If you would like to have the perfect base between Florence and Arezzo; Villa Il Borro at San Giustino Valdarno is a great option. With 10 bedrooms, an infinity pool with loungers, outdoor dining plus a beautiful garden and lounge area under a pergola. This is the perfect place to enjoy southern Tuscany with a little Dolce Far Niente (doing sweet nothing).

Finding accommodation in Tuscany is easy with luxury villa experts of Kinglike see their villas in https://kinglikeconcierge.com/tuscany-villas. Wherever you would like to spend your vacation they will provide the right villa for your party and interests.

Volterra 

Not far from the medieval town of San Gimignano, Velathri, or Volterra was one of the twelve main towns that belonged to the Etruscan civilization. The town walls were built to protect the ancient center and surrounding land from foreign invaders.

Volterra has a serene, historic center with narrow streets and beautiful squares. There are palaces and houses with towers typical of this region. 

Known worldwide for its hand-made alabaster objects, you could wander the little artisan shops and find something to bring back as a souvenir. 

Volterra became a little more famous in the last few years as the Twilight series storyline was based here and was the setting for some of the film's most dramatic and important scenes. However, while Volterra, is a real town, movies scenes were filmed in Montepulciano, another stunning little Tuscan village. 

Should you like to combine a visit to Volterra with the bigger towns, Siena is a short drive away. 

Montepulciano

Montepulciano is one of my favorite spots, a stunning village with a vibrant community. There are always lots of events on throughout the year and they also sell magnificient wine! 

This is is a medieval hilltop town surrounded by vineyards and it’s known for its vino nobile red wine. Other things to check out are the Torre di Pulcinella which is a clock tower topped by a figure of the Pulcinella, a commedia dell’arte character. Then on the Piazza Grande is the 14th-century Palazzo Comunale, with a tower offering panoramic views of the surrounding countryside and rolling hills. If you love to visit churches on your trips here there is also a beautiful Duomo, with a huge triptych above its altar.

To make this your home base and stay close by use this great location in rural tuscany in the nearby city of Cortona. Here you will find the spectacular Villa Ivana. With space for 18 guests, a private outdoor swimming pool, pretty covered outdoor dining area for up to 40 guests, its own private church and much more. 

Cortona

Often seen as a very livable city despite its ancient history, Cortona is a hilltop town with a little magic and a sense of the every day. 

For those you love to uncover the past the Etruscan Academy Museum displays a huge collection of bronze and ceramic items which show details of the town’s past. 

While this may seem like another walled town from a fairy story, Cortona feels like it could be somewhere to settle down. Though there are little narrow streets these are balanced with areas where you can see for miles across the landscape giving a feeling of light and openess.

Being a university town there is a vibrant atmosphere from the students and the creativity is felt throughout the city. There is everything you need here for a wonderful break from outdoor entertainment and music, local trattoria, artisan jewelry shops and delightful tipples from nearby wineries. 

For the the perfect location for your Italian dream vacation try Casale di Sant'Andrea at Sant' Andrea di Sorbello. With a helipad for your arrival, infinity pool, outdoor dining area under a pergola, pizza oven and tennis court there is very little reason to leave the estate! 

We hope you found these little hidden gems in Tuscany inspiration for your next Italian vacation. There is so much to explore here you can follow the tourist trail or find your own enchanting Tuscany away from the crowds. 

Disclosure: This is a collaborative post.