The Best Small Towns in Central Italy

Italy is arguably the most beautiful country in the entire world. From gorgeous sea-side towns like Positano and Manarola to iconic cities like Rome, Venice, and Florence, everywhere you turn you discover something beautiful. One of my favorite parts of Italy is the drive from Rome to Florence. I have done it many times and each time I try to stop off at another beautiful hillside town.

I am dedicating this blog to the beautiful towns of central Italy I have been to and including some great restaurants and top sights to see. I hope the next time you visit Italy, you rent a car and drive. The sights are unparalleled and you can do so much more in the countryside with the freedom of a car!



Arezzo is one of the larger “small towns” in East Tuscany. It’s only about an hour drive from Siena and Florence and is a beautiful place.

What to see & do:

  • Walk everywhere. It’s a small city center with plenty of room to walk and really explore
  • Corso Italia: this main road is a great street for shopping and people watching and connects the city center to the park
  • Piazza grande
  • Basilica of San Francesco
  • Cathedral: beautiful interior

Some great restaurants:


Siena is an hour south of Florence and an absolutely stunning city! the streets are narrow and steep and offer some beautiful views and traditional architecture. When you go, you’ll discover just why the center is listed as a UNESCO world heritage site.

What to see & do:

  • Piazza del campo: this large square is the perfect place to have a picnic and enjoy people watching.
  • Every year they host the Palio (famous traditional horse race) in July and August. The streets are flooded with people who come from all over to watch this impressive horse race that originates in this very square back to 1633! If you like excitement and tradition, make sure to plan your trip around the Palio.
  • Wednesday Market: Every Wednesday from 7am-1pm they host the largest market with food and art vendors everywhere near Piazza Gramsci. Get there early and enjoy the smell of coffee, fresh vegetables and delicious Italian local foods!

Some great restaurants:


When people think of Montepulciano they often think of their famous red wine, but the city itself is also a really beautiful one. It’s up a medieval hilltop city with views of Tuscany below and some gorgeous sunsets.

San Gimignano

A perfect small town in the heart of wine country, San Gimignano is a top destination for those on wine tours. At one point the city had 72 towers and is still referred to today as the “city of beautiful towers”



As the capital city of Umbria, Perugia is a beautiful city in the heart of Italy between Rome and Florence. There’s so much to see and do here and the city itself still has its gorgeous medieval walls and architecture giving it a really unique feel!

What to see and do:

  • Go to the EuroChocolate festival: for almost 100 years, Perugia has hosted this incredible chocolate festival in October bringing almost 1 million visitors every year! I’d recommend going for the day because hotel prices sky rocket but it’s delicious and a fun way to experience a festival in Europe!
  • Explore the medieval city walls
  • Ride the mini metro: it’s exactly what it sounds like, a tiny metro taking you from place to place in Perugia. It’s the best way to get from the train station to the city center!
  • Piazza IV Novembre: the largest square in the center and the perfect place to stop for gelato
  • Piazza Italia: beautiful views of the valley below and rest of the city from above

Some great places to eat:

  • Al Mangiar Bene: delicious fresh pasta and a great vibe
  • Perugina: their chocolate stores offer some of the best chocolate in Europe!


A tiny hillside oasis nestled in the hills of Umbria, Orvieto boats a gorgeous duomo with a mosaic facade. The best ways to get there are to drive up to the town or hike the city walls as locals do.

What to see & do:

  • Walk along Via del Duomo for some great shopping and end at the gorgeous duomo.
  • Head to the Palazzo del Popolo for a beautiful square and some gelato
  • Dine at Mezza Luna for an incredible Italian meal at a restaurant off the beaten path and favorite local hang out


Not far from Perugia is the incredible town of Assisi. The birthplace of St. Francis one of Italy’s patron saints, this town is well-known to catholics around the world. The views are iconic and the architecture is breathtaking.

Other things to do while exploring

  • Rent a room in a villa: Tuscany and Umbria are filled with amazing villas. Whether you’re looking for a place to get married, host a family reunion, or just enjoy a romantic getaway, these villas are the perfect oasis. Many of them offer food on site and pools and you can stay on any budget. From rustic beautiful country houses to grand villas the options are endless. Arguably our favorite is Casa Cornacchi Country House in Tuscany. They have a main villa you can rent exclusively, a small property you can rent for 10 people, or rooms and apartments you can rent for a few people. It’s the perfect getaway.
  • Spend an afternoon at the hot springs. Hot springs are all over the countryside and they are the perfect place to wind down and enjoy some time in a pool or a luxurious spa. Check out some free ones here!
  • Schedule a wine and olive oil tasting. If there was ever a perfect place in the world for this, it would be the heart of Italy. One of our favorites was Felsina S.P.A. right in Tuscany where they offer tours, wine tastings, and food pairings in a unique setting. It has its own town square and art exhibits in the massive storage areas.
  • Take a cooking class: love pasta, risotto, cheese, and wine? Why not try a cooking class in Italy! I discovered Cookly about a year ago and LOVED the experience. Search for the perfect class for you!

Thank you for following along on my journey through memories of central Italy. Buon viaggio and enjoy your trip!

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