Photo ©Proloco San Giovanni Valdarno
Three days in the Valdarno area
Medieval and contemporary art between Florence and Arezzo
40 km
Three days

Nestled to the north of Arezzo, to the east of the Chianti and to the south of Florence, the Valdarno region encompasses artistic masterpieces, an exquisite wine trail and wonders of nature as far as the eye can see. From Fra Angelico to DOCG and DOC wines to quaint medieval villages, a holiday in this area won’t disappoint seasoned Tuscany lovers and newbies alike. We’ve put together a three-day itinerary through this stunning corner of Italy’s beloved region.

For those staying in Florence or Arezzo, the itinerary can be broken up into individual day trips, or if you prefer to be on the road, book a room at a charming hotel in one of the historic centres for easy access.


First day
Medieval and modern in Montevarchi
 - Credit: Cassero per la scultura di Montevarchi

Our journey begins in Montevarchi, one of the most picturesque towns in the Valdarno. Its strategic position at the crossroads between Florence, Arezzo and Siena made this town a reason for bitter conflict for centuries. Thankfully, no such violence will mar our visit today as we wander its narrow streets and piazzas. Head to piazza Varchi, the centre of town and home to our first stop, the Collegiate Church of San Lorenzo, which houses a Museum of Sacred Art. The 13th-century church was originally Romanesque in style, but it’s transformation a few centuries later (1706) by Massimiliano Soldani Benzi gave its current Baroque appearance. The high altar houses the 17th-century “Reliquary of the Holy Milk”.

Tthe Museum of Sacred Art conserves a number of late-medieval and Renaissance masterpieces. One of these is the 15th-century Della Robbia Temple, a stunning example of glazed terracotta, reconstructed to how it was inside the church before it was disassembled in the early 18th century. The museum also vaunts a relief by Della Robbia depicting the delivery of the “Reliquary of the Holy Milk,” 16th-century processional cross by the Florentine goldsmith Piero di Martino Spigliati and liturgical décor, like a polished silver cross made in Benvenuto Cellini’s workshop.

Jumping forward several centuries, the Cassero for the Sculpture vaunts artworks from the 19th and 20th centuries. A fortified keep built by the Florentines in 1328, the Cassero today conserves over 2,500 works of bronze, marble, plaster, terracotta and designs, as well as period photographs and documentation. 

In between museum visits and site-seeing, you’ll surely want to indulge in some of the local food and wine! For meat eaters, make sure to try the delicious Valdarno tarese, a designated Slow Food pancetta aged for at least 90 days and produced in the Valdarno – Arezzo region. Stop by the butcher on via Burzagli for a real treat!

Second day
Winter warmth in San Giovanni
 - Credit: Proloco San Giovanni Valdarno

Our itinerary continues to San Giovanni Valdarno, a classic example of the so-called “new towns,” with a central piazza and porticoed streets. Art and culture can be found around every corner in this medieval town, from the magnificent churches to government palazzi and impressive museums. Our first stop of the day is Palazzo d’Arnolfo. Built in the 13th and 14th centuries, this building originally housed the civic council and representatives of Florence, which controlled the town. Indeed, it was centre of Florence’s power in the Valdarno, controlled by an appointed vicar: still today, the façade of the building is covered in the vicars’ coats of arms (there are over 250 of them!). For geography buffs, make sure to visit the Museum of the “New Towns", which narrates the history of the foundation of the new towns in the late Middle Ages, a period of growth in the population and commercial trade.

Contemporary art can be found at Casa Masaccio, which, contrary to its name, does not conserve artworks by the early Renaissance master, but rather, is housed in the building where it is believed he spent his childhood. The museum contains the permanent collection of the Municipality of San Giovanni Valdarno, and includes pieces by Italian artists like Alighiero Boetti, Giovanni Anselmo, Venturino Venturi and Massimo Bartolini.

Our last cultural stop for the day is Basilica of Santa Maria delle Grazie, built following a miracle in 1484 when a grandmother prayed for and received food to feed her grandson, whose parents had died from the plague. A portico and arched windows decorate the façade, which is topped with a triangular gable and bell tower. Below, in the centre, is a large polychrome terracotta by Giovanni della Robbia (1513) depicting the Assumption. Inside, we can find late-17th-cenutry frescoes by Giuseppe Nasini and Vincenzo Ferrati in the vaults and others painted to the left of the altar portraying the Miracle of Monna Tanci, presumably by a student of Perugino.

For more artistic treasures, head to the related museum next door. Here, you’ll find a wonderful collection of 15th-century paintings by artists such as Masaccio’s brother, Giovanni di Ser Giovanni, known as Lo Scheggia, Giovanni di Piamonte, Piero della Francesca’s student, and Fra Angelico, whose masterpiece The Annunciation is housed in the museum. The collection also includes a few 17th-cenutry pieces, vestments and historic documents.

If you happen to visit in January, don’t miss the Palio dello Stufato alla Sangiovannese, dedicated to the town’s most famous dish, San Giovannese stew, made with veal and chopped vegetables. The Palio was created to make sure the culture of this local delicacy doesn’t die out, and anyone can participate, adding their special takes to the recipe to the competition. A jury of experts and a “popular vote” decide the winners! For famous wines any time of the year, you can also pop over to the lovely Tenuta San Jacopo, a 15-minute car ride from the historic centre. Surrounded by vineyards and stunnig views of the Montevarchi countryside, you can try their seven different wines, two kinds of grappa and an extra-virgin olive oil.


Third day
Exploring Loro Ciuffenna and Castelfranco Piandiscò
Loro Ciuffenna
Loro Ciuffenna - Credit: Virginia Barone

The last leg of our three-day outing brings us to two lesser-visited towns, where pure authenticity hangs in the air. Our first stop is Loro Ciuffenna, the hometown of one of Italy’s foremost 20th-century artists, Venturino Venturi. Though the town is small, it boasts an extraordinary museum dedicated to its famed citizen, located in the former home of the sculptor. The museum conserves his body of work, an archive, photo library and media library. Some of the pieces on display include "The Ancestors and Seated Woman", while the gem of the museum is the artist’s workshop, preserved exactly as it was during Venturi’s lifetime. The museum is an obligatory place of pilgrimage for anyone who wants to learn more about 20th-century Italian art.

If you’ve got time before heading on to our next town, we highly recommend taking a drive out to the Parish Church in Gropina, two kilometres away. To admire Romanesque architecture in its richest form, this church from the 11th century is an absolute must. 

We conclude our itinerary in Castelfranco Piandiscò, a fairy-tale-like town surrounded by the very best of Tuscan nature. The town vaunts a range of architectural styles, from the medieval Arnolfo tower, all that remains from the original castle, to the 17th-century Church of San Filippo Neri, which conserves works by the Florentine workshops of Andrea del Sarto and Matteo Rosselli. The most renowned architectural site worth seeing in this town, however, is the Abbey of San Salvatore a Soffena, built in the 11th century. A papal seal issued by Urban VI brought the abbey under the jurisdiction of the nearby Vallombrosa, and the walls were all frescoed soon thereafter. Baroque modifications were made in the early 18th century, when that the frescoes were covered and replaced with altars and stuccos. The frescoes were rediscovered in the 1960s, and we can now admire stunning paintings by Renaissance masters, such as Paolo Schiavo, Rieti and Bicci di Lorenzo, as well as Lo Scheggia, who painted an "Annunciation".

Alternatively to Castelfranco Piandiscò, you can spend the afternoon at the enchanting Il Borro, an organic winery 20 minutes from Loro Ciuffenna, in the direction of Gropina. Here, you can get the full Tuscan experience as you take a cooking class, go truffle hunting, tour the vineyards and enjoy a tasting of the many wines.