The Best of Tuscany

When you think of Italy, what are some images that pop into your brain? The Roman Colosseum? Pizza? Mount Vesuvius? Gondola rides in Venice? Yep… those may come to mind. But, to many, images of gorgeous vineyards in the sun, sunflowers bursting with colour, and small quaint towns that display a simpler Italian lifestyle usually are what pops first into their brains. The good news is it’s not just an image or a fake stereotype in Italy: you can find all this in the Tuscany region of the country.

So, what are the best places to visit in Tuscany? Back in my college days, I was fortunate to live in Tuscany for a bit. Many of my day trips involved traveling to various villages and towns around the area. You really can’t go wrong exploring any of them, but there are some that are pure gems (in my opinion) that you should try and visit while you are here.

Montepulciano

With a population of 14,000, Montepulciano can be seen more as a town. It’s a medieval town with the beautiful 14th-century Palazzo Comunale. It is widely known for its deep red wines and its picturesque vineyards. Here, you will see some cute gift shops, wineries, oil and pasta shops, as well as cheese caves. It is a fun little outing to visit for the afternoon.

Cortona

If you’ve ever watched Under the Tuscan Sun, this is where the movie was filmed. Cortona has all the charms of a nice Tuscan town, but it also serves as the location for the Etruscan Academy Museum as well as many archeological sites that includes a part of the Roman road. Although it is more touristy than other parts of Tuscany, you will definitely want to spend the morning or afternoon exploring all the charm that Cortona brings.

Castiglion Fiorentino

Photo Credit: Trip Advisor

I might be biased, but I think Castiglion Fiorentino is a hidden gem in the Tuscan region. This was where I lived while I studied horticulture. At the top of the hill, you will see stunning sights of the Tuscan scenery all without bumping into people. You are truly relaxed and away from the crowds when you come here. It is not touristy, so you will not see any tourist activities or gift shops, but you will rather see Italy from a local’s perspective. There are wineries that includes activities like grape-harvesting, pizza-making, and hiking tours. There are fantastic restaurants at a fraction of the price of nearby villages. During the warmer months, the village comes alive with their outdoor markets and flag throwing competitions during the Monteriggioni Festival. Definitely worth a visit!

Pozzo della Chiana

Another hidden gem not far from Castiglion Fiorentino is Pozzo della Chiana. It is very small, but offers a wide range of sites and activities. There are several basilicas and archeological sites within the village, and also many, many wineries in and around the area. We personally love Agriturismo and Winery Fattoria Santa Vittoria. Among all the wineries we’ve been to, they have given us the best experience. On this last trip, we did a truffle hunting experience with their dog, Aisha, and we truly felt like family. You will definitely step out of the touristy areas when you travel over here and take some time for the quiet life in Tuscany.

Florence

Although not a small town, Florence is considered one of the best cities in all of Italy. It is the birthplace of the Renaissance period and has a plethora of art and history museums. Here, you can see the Uffizi, Galleria dell'Accademia (where you can find David), the Duomo, the museum of Galileo, and the Boboli Gardens. Florence is like one of the many cities in Italy, but with the Tuscan charm you get from the other nearby towns and villages in the region. You will have to come and visit Florence while you are exploring the region. It’s a must!