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Eastern Tuscany


Interior of the medieval Sansepolcro Cathedral

Sansepolcro is one of our favorite towns in the Eastern Tuscan region, almost sitting on the Umbrian border. This medieval town is nestled within its Renaissance walls, it is home to elegant towers and palazzi. The main street, il Corso, runs from Porta Fiorentina to Porta Romana and is dotted with stylish boutiques, upscale grocery stores, bars and restaurants. On Tuesdays and Saturdays, there is a farmers market as well as a couple of good stalls selling linen and shoes. It’s worth a trip for the tablecloths and the local glitterati!

As Piero della Francesca was born in Sansepolcro, il Museo Civico is a must-see. The museum houses many rare and unique works including La Resurrezione (the Resurrection). During World War II, the Resurrection saved Sansepolcro from destruction. Captain Anthony Clarke, ordered to bomb the town, remembered that Aldous Huxley had described the work as “the best painting in the world” and commanded his men to stop the bombardment at the very last minute.

This museum is never overcrowded and you don’t have to book weeks in advance. So you can enjoy rare works in peace.

Other artists include: Matteo di Giovanni, Sinbaldo Ibi, Gerin Pistoia, Raffaellino from the Hill, Santi di Tito, Giovanni de Vecchi, remigio Cantagallina, Andrea Pozzo and Augustine Ciampelli.

Taking the time to visit The Aboca Herb Museum is worth it…really. It is the only herb museum in Italy and tells the story of the ancient traditions of Herbal Medicine particularly during the Renaissance. They have a vast array of antique books, pestles and mortars, ceramic herb jars and glassware. An interesting way to pass an hour.

Sansepolcro’s Duomo (Cathedral) is also worth a visit.

Eating in Sansepolcro

The dining experience in Sansepolcro is one to be treasured. There are countless amazing options, and almost any pizza stand on a corner will serve to delight the palate.  Please contact us to access our ever-expanding list of favorite eateries around town.


Anghiari, in the Province of Arezzo, Tuscany

Voted one of Italy’s most beautiful hilltop towns, Anghiari is the picture-perfect medieval citadel. It is famous for the Battle of Anghiari in 1440 and “The Lost Leonardo”, a painting by Leonardo da Vinci, depicting the famous battle, now believed to be hidden beneath frescoes in the Palazzo Vecchio in Florence.

Its labyrinth of cobbled streets, ancient doorways and secret passageways transport you back to another time. After wandering through the narrow streets, rest on the benches at the top of the thirteenth-century fortress and enjoy the spectacular views over Tuscany and Umbria.

During the summer months, it hosts many local fairs and festivals, including the Anghiari Festival featuring classical music, chamber music, choral works and opera. The town is also known for its linens and antiques. Every Saturday, there is a local antique market.


Arezzo is the largest town in eastern Tuscany, north of Cortona and east of Siena. It is known for its medieval architecture and works of art by such masters as Ciambue and Piero della Francesca.

It’s worth visiting Piero della Francesco’s frescoes in the Chiesa di San Francesco. The fresco cycle was painted between 1452 and 1466 and is considered to be one of the masterpieces of the Renaissance.

Piazza Grande square in Arezzo, Tuscany, Italy

Piazza Grande square in Arezzo, Tuscany, Italy

The streets are windy and narrow and its squares were made to while away hours soaking up Italian life. Known for its fashion-forward designers, there is a strong sense of the aesthetic wherever you look. Wallet permitting, check out Sugar on the main drag, uber chic and nice salespeople!

The Arezzo Antiques Fair is the biggest in Italy, held on the first weekend of each month. The largest market takes place on 9, 10 and 11 September. the barn is full of bargains purchased at the fair.

Arezzo is also famous for an annual medieval festival called the Giostra del Saracino. In this, “knights” on horseback representing different areas of the town charge at a wooden target attached to a carving of a Saracen king and score points according to accuracy. Virtually all the town’s people dress-up in medieval costume and enthusiastically cheer on the competitors. Great fun for all the family.


The Medieval Town Gubbio

There’s no getting away from it, Gubbio is gorgeous. It’s worth the windy road to contemplate the town’s spectacular views.

It is also decidedly gothic. The town appears austere because of the dark grey stone, narrow streets and medieval architecture. But it has soul and the locals are friendly, keen to share their proud history. There are many sights to see including Palazzo dei Consoli, The Duomo (Cathedral) and the Palazzo Ducale, famous for its inner court, reminiscent of the Palazzo Ducale in Urbino.

Worth a visit is The Vivian Gabriel Oriental Collection. A museum housing a collection of Tibetan, Nepalese, Chinese and Indian art, donated by the British Colonial officer and explorer Sir Edmund Vivian Gabriel.

Gubbio is also known for its Palio, the Corsa dei Ceri. Every year on May 15, three teams run through cheering supporters up the mountain from the main square in front of the Palazzo dei Consoli to the basilica of S. Ubaldo. Each team carries a statue of their saint mounted on a wooden octagonal prism, similar to an hour-glass shape 4 meters tall and weighing about 280 kilograms.

Gubbio is also known for its pottery. A paradise for those seeking hand-crafted maiolica.


The road to Urbino is tortuous, but the town itself is nestled on a high sloping hillside, surrounded by olive groves and still retains much of its picturesque medieval aspect. It is home to the University of Urbino, founded in 1506, and is the seat of the Archbishop of Urbino.

The Italian city of Urbino with a view of the Palace of the Dukes of Urbino and the cathedral

Although it has Roman origins, its peak came during the 15th century when Duke Federico da Montefeltro established one of Europe’s most illustrious courts. The court attracted artists and scholars from all over Italy, influencing cultural developments throughout Europe. The Duke’s patronage nurtured many of the Renaissance’s most influential artists including Piero della Francesca, Raphael’s father, Giovanni Santi and Baldassare Castiglione who wrote The Courtier.

A must-see is the Palazzo Ducale where the Duke and the court lived. It still houses one of the most important collections of Renaissance art in Italy. It is also worth visiting Raphael’s house, the Duomo and the “Pierina Scaramella” botanical gardens.



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