Tuscany Off the Beaten Path – 5 Reasons to Visit Certaldo

Tuscany Sunset

5 Reasons to Visit Certaldo for an authentic Tuscany experience

Tuscany Off the Beaten Path – 5 Reasons to Visit Certaldo

Diving into Tuscan memories

Soft hills shaped the horizon as I watched one of the most beautiful sunsets I had ever seen. It had just rained heavily and the hills had created an echo of the roaring thunder, as if it was to answer the earth’s outcry for some rain. Now the thunderstorm was gone and the raindrops on the floor joined the ever-hot air by creating a mist over the vineyards as far as the eye could reach. Sunrays pierced the rising wall here and there, only to be stopped right on my face, glowing of happiness.  

This is the memory that will stick with me about the Certaldo area forever. Certaldo, located between Florence and Siena, is often overshadowed by the glamorous Tuscan cities and towns like Pisa, Lucca, and its close neighbours. However, in Certaldo, I felt like we had found the “real deal”. Of course, there were some tourists. What we saw most, though, were grandmas lining up on their plastic chairs in front of their home until late at night, or Italian suppliers arguing behind their Piaggio Ape.

If you want a little bit of the Tuscany off the beaten path as well as a charming and quiet atmosphere you simply must visit Certaldo.

1. Certaldo is full of VERY old history and art

Certaldo is not only known to be as old as Etruscan times, but is also famous for being the birth and death place of Giovanni Biccaccio, the alleged father of Italian poetry and literature of the 14th century. Certaldo Alto, the historical center of Certaldo that is set upon a hill, rising out of the 17th century extension of the town named Certaldo Basso, is preserved perfectly. In 1164 Federico Barbarossa, a Roman Emperor, turned the town over to the Counts Alberti of Prato, which is when it was named for the first time in historical artifacts. Only 20 years later Certaldo was taken under the control of Florence.

The structure of the town is unique. Instead of a piazza, you will find yourself ending up on the Via Boccaccio again and again. The location of the hill did not give enough space for the traditional piazza as in other medieval towns of the region. At the end of the Via Boccaccio, you will find the Palazzo Pretorio. It’s still preserved from the original times of the town and used to serve as the house of the Counts of Alberti. Take a look up to the ceiling and the walls where you will find colorful medieval paintings, that represent the families of curacies. 

Every July Certaldo is the host of a festival for street artists from all of Europe. I could not witness it myself, but it might be a nice time to go.

2. The surrounding area and the Chianti region

When thinking of Tuscany, we think of olive plantations, never-ending hills with vineyards and alleys wrapped by lines of cypresses.  The Chianti region, especially the area surrounding Certaldo, can offer all of these views without having to navigate anywhere. Simply take a right into that rocky road up to the next mountain and after a long and bumpy trip, you will be rewarded with views like these.

The landscape of the Tuscany, especially the infamous Chianti region, has something soothing to your soul. It is completely extraordinary and cannot be found as such anywhere in the world. There are beautiful beaches in a lot of amazing places, even mountains you can find in various spots of the world, but nowhere you will discover the characteristic views of the Tuscany. For this reason, I would recommend to always rent a car when visiting this amazing part of Italy. The cities are beautiful, as well, and even Certaldo can be reached by train. However, real freedom to explore the landscapes comes only with a car (or a bike if you are daunting enough).

3. The food & the wine

Certaldo food, tuscany off the beaten path

I am sorry that I am only going to talk about this one restaurant in this blog post. But if I could I'd eat here every day until I die. I am NOT exaggerating, and I am NOT getting paid for this. Just legit overwhelmed with how good the food was. 

About 20 minutes out of the city of Certaldo there is a restaurant up the hills, passing the rocky roads of the vineyards and a friendly old donkey, that will take your breath away. It does not only include the views that I so romantically described earlier but will also drive your taste buds crazy. Bring an empty stomach because this is where you will probably order the Antipasti, Primi Piatti, Secondi Piatti and Dolci-Combo – which basically means an entry dish, pasta or risotto, meat or fish and then a dessert. If you are already counting the price in your mind, don’t worry: it is very affordable! If you want to bring home some delicious wine and goodies for your family and friends, this is the place to shop as well. The restaurant combines tastings of their home-made products with your dinner – no strings attached, though! Just sit back and enjoy. Buon appetito!

4. Certaldo's views

Not only the surrounding region but also the old-town of Certaldo (Certaldo Alto) has spectacular views. And with views, I do not only mean the way the town overlooks everything, but also the way it looks itself. Little has been added to the town since its construction in the early middle ages. Therefore it will transform you in a time long past, where people exchanged apples for bred on the Via Boccaccio, and when its namesake Giovanni was writing poetry by the town's gates. 

5. Certaldo's Location within the Tuscany


Embedded in between Florence, Siena and San Gimignano, Certaldo makes for the perfect base town to take a road trip through the heart of the Tuscany. Especially if you have a car, you will be able to stay around the village in

Pinterest 5 Reasons to visit Chertaldo

Like it? Pin it!

Logo FTC

We are a team of three feminist travelers coming together from different parts of the world to share with you what we have learned from traveling, living, loving, and exploring all over the world. Join us and tell your story about female solo travel, relationships, mental health, city guides, or whatever else comes to your mind.

Berlin-based author of this text is Larissa, founder of the Female Travel Collective, solo travel lover and convinced feminist! 

Berlin-based author of this text is Larissa, founder of the Female Travel Collective, solo travel lover and convinced feminist! 

Become a Writer for the FTC