Explore Tuscany’s Hidden Gem, The City of Arezzo

By Linda Funay McCarley

About an hour southeast of Florence, the enchanting medieval city of Arezzo is a worthy stop on your Tuscan adventure, easily reached by car or train from Rome, Siena or Florence.

Arezzo lies at the confluence of four beautiful valleys near the border of Tuscany and Umbria, with the surrounding rolling hills undulating toward the majestic Apennine mountains to the east.  Shades of Florence reside here, visible in Arezzo’s abundant art, history and culture. And Arezzo is home to the largest antiques market in Italy!

Somehow this beautiful city has stayed under the mass-tourism radar, giving it a more relaxed and local feel than Tuscany’s more touristy towns.

My family and I enjoyed eight fabulous days in this vibrant city and found it to be an excellent anchor for exploring Tuscany and Umbria, and to revel in Arezzo’s many riches while enjoying its friendly local vibe.

Arezzo’s History

Long known as the city of gold and high fashion, traditions run deep in this former Etruscan city dating back to the 9th century BC. The Romans took over the city in the 3rd century BC, creating a strategic and thriving Roman center named “Arretium”. Remains of Arezzo’s Roman Colosseum are still standing today.

 Because of its accessible position to the mountain passes, Arezzo has constantly struggled with occupation over the centuries, especially during its medieval and Renaissance periods.

Medici Fortress (Fortezza Medicea)

At Arezzo’s highest point sits the remnants of the powerful Medici reign, its dominating fortress. Built by Cosimo I di Medici in the 16th century on top of Arezzo’s existing seats of power, the fortress reinforced the Florentine dominance in the city.

From the fortress, visitors can enjoy panoramic vistas of the valley and surrounding countryside, and the Apennine Mountain range provides the perfect backdrop in the distance. The leafy park next to the fortress is a lovely place to wander or just relax on a bench while taking in the scenery.

Piazza Grande

Just below the Medici fortress sits Arezzo’s main square, Piazza Grande, which has been known as the town’s focal point and main marketplace since ancient times. For movie buffs, the piazza is also famous for being the location of the 1997 Oscar-winning film Life is Beautiful (La Vita e Bella).

Take a spot for lunch in a lovely cafe under the beautiful arches of the Palazzo delle Logge. Then, wander through the antiques and artisan shops housed in the colorful medieval and Renaissance buildings that line the square.

Make sure to climb to the top of the clock tower of the Palazzo della Fraternita dei Laici, for its birds-eye views of Arezzo and the surrounding area.

At the lower end of the piazza sits my favorite little alley representing Arezzo’s medieval architecture. Here we enjoyed relaxing with an aperitivo on the small patio of Chiantineria, the coziest little wine bar and café. I loved watching passersby and looking upward in awe at the magnificence of the 11th-century Church of Santa Maria della Pieve, with its stunning, semi-circular apse facing onto the piazza.

Take a Stroll

Getting around Arezzo’s historic center is easy and pleasant, as the city is very walkable (albeit hilly). The Corso Italia serves as the city’s main street, a wide pedestrian boulevard perfect for strolling, browsing, and shopping in the city’s upscale fashion stores and impressive artisan shops.

Fuel up with a cappuccino and cornetto at historic Bar Stefano, and don’t miss ducking into one of the little alleys off Corso Italia during Happy Hour. You’ll find outdoor patios lively with locals and visitors enjoying an Aperitivo.

Our favorite family restaurant was Il Cantuccio, down at the bottom of Corso Italia. Recommended by locals, we loved the homey vibe and the menu that promised and delivered a good selection of traditional Tuscan and Aretini dishes such as Pici pasta with Wild Boar sauce, gnocchi with porcini mushrooms, and tagliatelle with truffles.

Reading the family’s motto on their menu was all we needed to convince us to cross their threshold:

“We still make pasta the way it used to be –

Love and passion”

In the historic center, there is a good variety of casual and more upscale restaurants to choose from. After dinner, make sure to wander around Arezzo as the town sparkles in the evening light, with its softly lit buildings and the alleys and lanes exuding warmth and a romantic aura. You may happen upon an impromptu live music performance or just enjoy seeing the locals out and about enjoying their city.

Art History in Arezzo

Art lovers will revel in the city’s rich works, found in its beautiful churches from the medieval and Renaissance periods. Celebrated Renaissance artist Piero della Francesca made his mark on Arezzo, and his works should not be missed.

Basilica of San Francesco

Inside the Basilica of San Francesco you will find Piero della Francesca’s incredible Early Renaissance fresco cycle, depicting the Legend of the True Cross.

While the church looks fairly unadorned on the outside, once inside prepare to be impressed with this stunning fresco cycle. Completed in 1466, this work is said to be the highest expression of Renaissance art.

Arezzo’s Cathedral

The imposing Cattedrale di San Donato, known by locals simply as The Cathedral, sits atop a hill on a pre-existing Paleo-Christian church, and possibly of the ancient city’s Acropolis.

The cathedral houses another of Piero della Francesca’s masterworks, the Fresco of Saint Mary Magdelene. Also on view are stunning works by Vasari, Della Robbia and Donatello.

Vasari Home and Museum

Visit the Home of Renaissance artist and architect Giorgio Vasari, an Arezzo native known for his work on Florence’s Palazzo Vecchio and Uffizi Gallery.

From 1542 to 1568, Vasari painted his frescoes on the ceilings and most of the walls of his home, a true example of an artist’s expression and worthy of a visit.  Vasari was also known as the Father of Art History, largely attributed to his book The Lives of the Most Excellent Painters, Sculptors, and Architects, published in 1550.

Bringing the Past to Life – Joust of the Saracen

Arezzo and the surrounding area have a long history of celebrating ancient traditions, with the city’s most famous celebration being the Joust of the Saracen.

Plan a visit in June or September to witness this festival and historical reenactment of the colors, flavors and sounds of medieval Arezzo.

This important social function in Arezzo’s community kicks off with a colorful procession of over 300 costumed residents and 27 horses parading the city’s streets. 

For the tournament, the “knight” representing his team or “quarter” gallops on horseback along the jousting track in Piazza Grande,

aiming his wooden lance at the Burrata and its shield. The knight who hits the target on the shield the most times wins the Golden Lance for his quarter.

And then, they celebrate.

Antique Market

Equally as popular is the monthly Antique Fair (first Sunday of the month), famous all over Tuscany for its huge selection of vintage items.

Arezzo’s Antique Fair is the largest one in Italy. Over 500 stalls line the cobbled lanes surrounding the Piazza Grande, continuing under the loggia and flowing out into the center of the piazza. 

Browse side-by-side with locals and expats shopping for exquisite furniture and art for their Tuscan villa, or take a small piece of Italian history home with you as a memento. I was ecstatic to find my own initials monogrammed onto a set of vintage napkins.

The Piero della Francesca Trail

If seeing della Francesca’s work leaves you wanting more, take the “Piero della Francesca Trail”.  We did this by car in an afternoon and found it an easy and pleasant drive from Arezzo, through the rolling hills of Tuscany.

Start in della Francesca’s birthplace, the lovely town of Sansepolcro. Here the civic museum houses two of his pieces, the Madonna della Misericordia, an altarpiece, and the fresco, The Resurrection of Christ, which English writer Aldous Huxley has described as “the greatest painting in the world”.

On your way back to Arezzo, stop at the tiny hamlet of Monterchi where one small museum is dedicated to della Francesca’s Madonna del Parto (the Pregnant Madonna). An enclosed theater with benches provides a lovely spot to sit and quietly absorb this unique piece, and to reflect on the artist’s use of linear perspective and foreshortening techniques. An adjacent Education Room illustrates della Francesca’s pioneering techniques in detail.

DaVinci’s Bridge

For a special treat, take a side trip to the little town of Laterina just outside of Arezzo. Art historian Silvano Vinceti has recently identified the Romito di Laterina bridge as the bridge painted by Leonardo da Vinci in the backdrop of his 1503 masterpiece, Mona Lisa. For many years another town, Buriano, has laid claim to the famous bridge depicted behind Mona Lisa’s left shoulder. See if you can settle the debate.

Wine, Cheese and Prada

In Arezzo you are close neighbors with Chianti, known as one of the best wine regions in Italy. Wineries and tasting rooms are easy to find throughout the area. Further south near the beautiful Val D’Orcia are the hilltop towns of Montalcino and Montepulciano, known respectively for their famous Brunello and Vino Nobile di Montepulciano wines.

We were curious to see how the delicious local cheeses in Arezzo were made, so we booked a tasting at a family-run sheep farm located 30 minutes from Arezzo. We spent a wonderful morning witnessing cheese-making by hand, visiting the farm animals (I got to hold a little lamb!), and sampling the delectable cheeses we had learned about. There is nothing like the taste of fresh-made cheese from a sheep farm.

To round out our day trip we made a pilgrimage to the huge Prada outlet (called Space Outlet) in Montevarchi, which was right on our way back to Arezzo.  If you’re into designer handbags and even if you’re not, this is a fascinating store with some (relatively speaking) good deals to be had.

Where To Stay in Arezzo

There are a number of smaller hotels and vacation rentals in Arezzo. We were extremely happy with our vacation rental, Locanda Bellavita. In the perfect position a short walk from Arezzo’s main parking lot, Locanda is a 10-minute walk to Piazza Grande and a leisurely stroll to most of the nearby historic sites and services.

This elegant apartment is on the main floor of a 16th-century building and was once the servants’ kitchen for the main villa, evidenced by the huge fireplace in the living room. Owner Stefano completely restored the 3-bedroom apartment himself, with a keen eye to the perfect mix of historic ambience with all the modern amenities you could ask for.

In the early mornings my favorite thing was to skip right across the street to the lovely bakery Pasticceria F.lli Bruschi, where a smile from the lovely ladies was guaranteed, and some of the best pastries in Italy were waiting to grace our breakfast table. 

There are many gems to uncover in the city of Arezzo – stop in for a day, or take a few days to linger and really soak in its history, art, architecture and magical aura.

Helpful Abrezzo Links:

Arezzo Apartment Locanda Bellavita

Sheep Farm and Tasting – Podere Casa Al Bosco

Arezzo Walking Tours/Things To Do