Halfway between Florence and Siena lies a delightful medieval town perched on a hilltop: Certaldo. Still relatively unknown to the crowds of tourists who invade Italy between April and September, Certaldo preserves a magical, authentic atmosphere. The town is divided into two areas: Certaldo Alta, the charming and historic old town, and Certaldo Bassa, the more modern lower section.
I had the pleasure of discovering Certaldo in April 2016 as part of a press tour organized by the local tourism board, Visit Certaldo. We enjoyed a day full of culture, gastronomy, and unexpected surprises.
Here are ten reasons why you should consider adding Certaldo to your Tuscany itinerary.
1. Ride the Funicular to Certaldo Alta
One of the most scenic ways to reach Certaldo Alta is by taking the funicular from Piazza Boccaccio in the lower town.
In just over a minute, you’ll glide up the hill and arrive in the heart of the medieval village, enjoying a lovely panoramic view along the way.
The funicular fits up to 30 people and runs every 15 minutes. Check the Autolinee Toscane website for opening hours and ticket prices.
2. Walk Through a Truly Medieval Town
Certaldo Alta offers a real journey back in time. You’ll find medieval towers, gates, palaces, fountains, and even ancient prisons.
Unlike many other Italian towns, Certaldo doesn’t have a traditional central square. Instead, the gathering spot is at the wider end of Via Boccaccio, near the impressive Palazzo Pretorio.
A professional guide can make your visit even more fascinating with stories and historical details about this enchanting village.
3. Sip a Beautifully Decorated Cappuccino
Italians love starting their day with a creamy cappuccino at the local bar. At Bar Boccaccio on Certaldo’s main street, they take things a step further with caffetteria artistica—delicately decorated cappuccinos that are as delightful to look at as they are to drink.
Take a seat at one of the outdoor tables and enjoy the charm of the town with your morning coffee.
4. Visit the House of Giovanni Boccaccio
Certaldo is famously the hometown of Giovanni Boccaccio, the 14th-century poet and author of The Decameron. His home is located at number 18 on Via Boccaccio and is open to visitors.
After Boccaccio’s death, the house changed owners several times until it was purchased in the 19th century by Carlotta Lenzoni de’ Medici, a friend of poets like Leopardi and Byron. She transformed it into a small library in honor of Boccaccio’s legacy.
Although partially destroyed during World War II, the house was restored and reopened. Today, it contains a historic library with rare books from the 16th to 18th centuries, including foreign translations of The Decameron.
Make sure to climb the tower at Casa di Boccaccio—it offers a stunning panoramic view, and it’s where I took the photo featured at the top of this article.
5. Admire One of the Oldest Women’s Shoes in the World
Inside Boccaccio’s house, you can see a pair of remarkably well-preserved women’s shoes discovered in a hidden wall cavity after the bombing. Experts believe they date from the late 14th to early 15th century.
Their preservation is thanks to their proximity to a chimney flue, which kept the area dry.
The shoes feature high heels and decorative details—designed for the tiny feet of the time. Yes, even in the Middle Ages, women wore heels!
6. Discover the History of Palazzo Pretorio
At the end of Via Boccaccio stands the imposing Palazzo Pretorio, adorned with ceramic coats of arms and frescoes. Originally a noble residence, it later became a public building with a serious purpose: criminal trials, including capital punishment.
One of the old prison cells still bears a chilling message written in candle soot:
“Oh friend, things are bad for you because when you enter this cell, you are no longer master of your destiny. Giambadia knows this and says it to you.”
The ceramics are beautifully preserved and reflect the region’s artisanal heritage.
7. Learn Traditional Ceramic Painting Techniques
After admiring the historic ceramics of the Palazzo Pretorio, why not try your hand at this Tuscan tradition? At Artesia, a workshop in the heart of Certaldo Alta, you can take a hands-on ceramic painting class.
A 2-hour workshop for up to 8 people costs €40 + VAT, and you get to take home your creation. Prefer just to observe? A 30-minute demo for up to 40 people costs €60. Classes are available only in Italian or English. If you’re just looking for a souvenir, the studio also offers a variety of hand-painted ceramics. This experience is already on my wishlist!
8. Make a Wish at the Nail Museum
Yes, you read that right—Certaldo is home to a quirky Museum of Nails, created by local artist and carpenter Giancarlo Masini. The small collection includes ancient farming tools, a nativity scene made entirely of nails, and even a bottle where visitors are invited to make a wish.
The sign reads: “Take a little nail, rub it, make a wish, and drop it in Beppe Chiodo’s bottle.”
I did. Will it come true?
9. Explore the Mysterious Story of the Blessed Giulia
One of the most intriguing local legends is that of Beata Giulia. Known for saving a child from a burning tower without sustaining a single injury, she later chose to live walled inside a tiny cell with only two windows—one facing the main street, another looking into a cloister.
She spent the rest of her life praying on her knees, relying entirely on food donations from townspeople. According to legend, whenever a child brought her bread, she returned the favor with fresh flowers—no one knows where they came from.
Her remains rest at the Church of SS. Jacopo and Filippo. You can visit her cell, now with one wall open, and see the cloak she was wearing when she passed away—a cloak that, reportedly, is still used in exorcisms today.
10. Taste Local Delicacies in a Truly Tuscan Setting
Our lunch in Certaldo was unforgettable. We tried local favorites like pappa al pomodoro, coccoli (fried dough) with cured meats, and pecorino cheese served with onion jam made from the famous Certaldo red onion.
Don’t forget to buy a small jar as a souvenir in one of the shops. And of course, everything was paired with delicious Tuscan wine.
If you’d like to take a little piece of Certaldo home with you, check out the Cucina Giuseppina online shop!
I even shared a video of our lunch on Instagram—go take a look!
Still want more? Don’t miss the opportunity to visit the studio of artist Silvia Borgogni and her art print workshop. Check out Certaldo’s cultural calendar for major events like Mercantia, one of Italy’s most beloved street theater festivals, or the medieval open-air dinner held in June.
Another experience on my wishlist is a visit to Fattoria Majnoni, just a 10-minute drive from Certaldo’s center, where you can enjoy organic food and wine tastings. You can even book a English-speaking guide through GetYourGuide.
Special thanks to everyone who welcomed us so warmly—from Mayor Giacomo Cucini and tourism officer Francesca Pinochi, to Professors Massimo Tosi and Francesca Allegri, Sabrina Taddei and the “Ipotesi Teatrale” association, the restaurants A Casa Tua, Antica Fonte, Il Castello, Bar Boccaccio, the artisans at Palazzo Giannozzi, and the Compagnia del Drago Nero. Thank you for a beautiful day filled with culture, food, stories, and unforgettable views. My family and I absolutely loved it!
Read the original article in Portuguese here.
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