Certaldo is a charming medieval town in the heart of Tuscany, offering a wealth of cultural and historical attractions. Wander through the atmospheric streets of Certaldo Alto and discover unique places that bring the town’s past to life. The surrounding area features beautiful hills, castles, and picturesque villages that are perfect for a day trip. Thanks to its blend of history, nature, and authentic Tuscan charm, Certaldo is an ideal destination for curious travelers. In this article, you’ll find 11 great tips on what to see and do in and around Certaldo.
Contents – 11× Things to See and Do around Certaldo
1. Stroll Through Certaldo Alto
A walk through Certaldo Alto feels like stepping back into the Middle Ages. As you wander through the narrow brick-lined streets, you’ll encounter historic buildings, charming squares, and hidden passageways. The route takes you past highlights such as Palazzo Pretorio, ancient city walls, and Boccaccio’s house. Along the way, you’ll enjoy peaceful surroundings, authentic Tuscan charm, and sweeping views of the surrounding hills. This walk is the perfect way to fully experience the history and atmosphere of this special hilltop village.
2. Certaldo Funicular
The Funicolare di Certaldo is the easiest — and most fun — way to reach medieval Certaldo Alto. This cable car connects modern Certaldo Basso with the historic upper town and offers lovely views over the Val d’Elsa during the ride. In just a few minutes, you’ll find yourself in the atmospheric streets of Certaldo Alto without having to climb uphill. The ride itself is an experience and a perfect starting point for a historical walk through the upper town. A trip up or down costs just over one euro.
3. Palazzo Pretorio
Palazzo Pretorio in Certaldo is an impressive medieval palace that served as the administrative heart of the town for centuries. The robust façade adorned with numerous coats of arms immediately reflects the rich history of Florentine governance. Inside, you can admire original frescoes, old prison cells, and historic rooms that vividly illustrate the past. From the tower, you’ll enjoy a stunning view over the hills of the Val d’Elsa.
Tip! Want to learn more about visiting and the history of this palace? Read the article Palazzo Pretorio in Certaldo: The Medieval Heart of Tuscany.
4. Casa Boccaccio
Casa Boccaccio in Certaldo is the birthplace of the famous Italian writer Giovanni Boccaccio, author of The Decameron. The house has been transformed into a museum offering a fascinating insight into the life and work of this medieval literary icon. Visitors can wander through authentic rooms, admire original furnishings, and view historical documents and manuscripts. Its location in Certaldo Alto makes it easy to combine with a stroll through the picturesque medieval center.
Tip! Curious who this medieval writer was? In Casa Boccaccio – Who Was This Controversial Italian Writer? you can learn more about his life and home.
5. Chiesa dei Santi Jacopo e Filippo
The Church of Santi Jacopo e Filippo is a beautiful medieval church in the heart of Certaldo Alto. This historic religious building is known for its impressive architecture and atmospheric interior. Inside, you’ll find valuable artworks including paintings and religious icons from various centuries. The church is an important cultural and spiritual center for the town and offers visitors an authentic glimpse into religious life of the past.
Tip: The church houses Boccaccio’s tomb and the intriguing findings related to Giulia Della Rena. Read more in the article Church of Santi Jacopo e Filippo – Discover the Tomb of Boccaccio.
6. Italian Cooking Class
A cooking class in Tuscany is a unique way to experience the region’s rich culinary traditions firsthand. During the class, you’ll learn to prepare authentic Tuscan dishes — from fresh pasta to local sauces and desserts. Classes are offered in many locations, including at Bassetto Guesthouse where I stayed during my trip. Beyond cooking, you’ll discover the stories behind the ingredients and regional food traditions. For culinary travelers, a Tuscan cooking class is an unforgettable experience that perfectly blends culture, history, and flavor.
Tip: You can book great cooking-class day tours in Tuscany through GetYourGuide.
7. Museo di Arte Sacra
The Museo di Arte Sacra in Certaldo is a fascinating museum showcasing the region’s religious art and history. Visitors can admire medieval sculptures, paintings, liturgical objects, and precious manuscripts. The museum is housed in a historic building that enhances the authenticity of the collection. Guided tours and information panels offer insights into the meaning and origins of the displayed artworks.
Tip! Interested in Certaldo’s local history? Then read the article Museo di Arte Sacra – Discover Certaldo’s Religious Treasures.
8. Wine Tour Through the Chianti Region
A wine tour through the Chianti region is an unforgettable way to discover Tuscany’s famous wines and picturesque landscapes. During the tour, you’ll visit historic vineyards and authentic wineries where you can taste Chianti Classico and other local specialties. Experienced guides explain the production process, grape varieties, and the region’s long winemaking tradition. In addition to the tastings, you’ll enjoy sweeping views of rolling hills, olive groves, and medieval villages.
Tip! You can book wonderful wine tours in Chianti through GetYourGuide.
9. Florence
A visit to Florence is an unforgettable experience for anyone who loves art, history, and Tuscan culture. The city is renowned for iconic sights such as the Duomo, the Uffizi Gallery, and the Ponte Vecchio. As you wander through the medieval streets, you’ll discover charming squares, impressive palaces, and centuries-old churches. Florence also offers countless opportunities to enjoy Tuscan cuisine in authentic trattorias and markets.
Want to read more about this stunning city in Tuscany? Check out the Historical Travel Guide to Florence!
10. Siena
A visit to Siena transports you back to medieval Tuscany, thanks to its well-preserved historic center and characteristic narrow streets. The city is famous for its striking Piazza del Campo, the Gothic town hall, and the beautiful Siena Cathedral. As you explore, you’ll encounter centuries-old churches, lively squares, and authentic Tuscan architecture that reflects the city’s rich history. Siena also offers a unique chance to experience the world-famous Palio horse race and taste delicious local specialties.
Want to learn more about this beautiful Tuscan city? Read the Historical Travel Guide to Siena!
11. San Gimignano
A visit to San Gimignano offers a magical journey into medieval Tuscany, known for its well-preserved towers and historic center. Wander through the narrow streets and discover beautiful squares, centuries-old churches, and charming shops filled with local crafts. The town is also famous for its world-renowned white wine, Vernaccia di San Gimignano, which you can taste directly at local wineries. Visitors are treated to panoramic views of the Tuscan hills — perfect for photos and peaceful moments.
Want to read more about the Manhattan of the Middle Ages? Check out the Historical Travel Guide to San Gimignano!
Plan your trip to Certaldo & Italy
Accommodation?
Certaldo is a good base for exploring the province of Tuscany
Book your Hotel or Guesthouse here
Tickets & Tours?
In Certaldo Alto you will find a number of nice museums that are really worth visiting. With a combi-ticket for these museums, a nice lunch and an evening dinner, you can easily spend a whole day. Or book other fun activities in Tuscany!
Looking for the Best Activities? Book the best Tickets & Tours here via GetYourGuide
Flight tickets to Italy?
To Tuscany, it is best to fly to Florence or Pisa. Other options are Milan and Rome and then by train to Florence
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Rent a car?
The best way to explore Tuscany is by car!
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Public transport?
Are you going to explore Tuscany by public transportation? By train you can easily get to cities such as Florence, Lucca, Pisa or Siena.
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Do you have any more tips, ideas, or comments about this article on 11 sights in and around Certaldo? Feel free to leave a message below!
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