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To the west of the city of Arezzo lies the valley of Valdichiana and the picturesque roads that crisscross the valley, villages and vineyards.

The Charming and Beautiful Province of Arezzo

The province of Arezzo has much to offer, even though it is often not included on the main itineraries of Tuscany. You’ll find fewer visitors and more locals, as well as the treasures in the towns such as Cortona, Anghiari, Monterchi and Sansepolcro. There are medieval fortresses to explore, like the beautiful castle of Poppi, wonderful shopping, especially if you catch the antique fair in Arezzo and an abundance of exceptional cuisine.

Arezzo is one of the wealthiest cities in Tuscany, due to its artisan work by goldsmiths. Located in southeastern Tuscany, it sits atop a hill at the crossroads of four valleys: the Val Tiberina, Casentino, Valdarno and Valdichiana. Its ancient origins are verified by the stone tools found that date back to the Paleolithic era. The Etruscan town of Aritim was founded around the 9th century BC and quickly became one of the most important cities in Tuscany, playing an important role during the Roman era, due to its strategic position along the Via Cassia.

Even though the medieval center was destroyed during World War II, the city still has plenty of monuments, churches and museums remaining that offer visitors a chance to step back into history. The Church of San Francesco is probably the most famous in Arezzo, with an early Renaissance fresco cycle by Piero della Francesca depicting the Legend of the True Cross. You then head uphill to Piazza Grande, then on to the Medicean Fortress, which offers an incredible view of the countryside.

Arezzo may be somewhat unassuming and is a relaxing change of pace. For those who stop in the city, you will find that it gently invites you to stroll its streets and admire what many would call a true open air museum. The city’s actual museum is well-organized and provides a wealth of information about the Etruscans, whose language gave the region of Tuscany its name -Tusci. The historical center is a vibrant place where stores, restaurants, artisans and shop owners serve the general public. And although you will find many menus in multiple languages, the city really revolves around its local residents. Since tourism takes a backseat to ‘la bella vita,’ it is a refreshing place to visit.

The Roman portion of Arezzo was destroyed during the Gothic War and also following the invasion by the Lombards; however, the town grew in importance during medieval times and was characterized by many towers and architectural contributions during the period. This prosperous era ended when the city challenged Florence for supremacy. After the disastrous Battle of Campaldino in 1289, Arezzo struggled to stay on the map until it finally gave in to Florence. Cosimo I de’ Medici, Grand Duke of Tuscany, built the Fortezza which dominates the top of the hill overlooking the conquered city.

One might expect that the city would want to shy away from its medieval past, but nothing could be further from the truth. Arezzo conducts a re-enactment of an age-old event called the Giostra del Saracino – Joust of the Saracen, which is held twice every year – on the third Saturday in June and on the first Sunday in September in the beautiful Piazza Grande.

The whole city seems to turn up in medieval costume, with over 300 participants recreating the medieval atmosphere, as the quarters of the city compete against each other in a joust to win the Golden Lance. There are eight knights for each of the quartieri of the city – Porta del Foro, San Andrea, Porta Santo Spirito and Porta Crucifera. Each knight gallops on horseback with a wooden lance and aims at the Buratto and its shield. The Buratto symbolizes the King of the Indies and he is armed with a shield in the left hand, which is the target. It is divided into 10 blocks, each one corresponding to a certain number of points. In addition to the joust, there is theatrical and musical entertainment. Additionally, during the festival, the city hosts one of the largest antique fairs in Tuscany.

For film buffs, Piazza Grande was prominently featured in the film “Life is Beautiful” by Roberto Benigni. Today you will find that several fine restaurants line the square, which also is surrounded by historic homes and beautiful monuments. The atmosphere is of an age long gone and it is the perfect place to sit and people watch.

Walking is the best way to enjoy the city. True, it is on a hill, but it is definitely worth the visit and the walking. In addition to the Archeological Museum and the Art Museum, you can fill the day with little detours into the many notable churches, piazzas and cafes.

Outside of the city, I Giorni del Vino – The Days of Wine, is a fantastic event promoted by the province which focuses on the Colline Aretine wine production and picturesque vineyards. It is a wine tasting event that features a different vineyard every Wednesday and Sunday from late April through mid-October. Unlike Chianti and Montalcino, the Arezzo landscape is not known for its sprawling vineyards and soft hills. Rather, space is at more of a premium, since vineyards share the land with the production of orchards. Grape vines are sometimes even hung on trees such as walnut and fig to save space. Wine production in the area offers a wide selection of award-winning vintages of both red and white.

The town of Lucignano has been strategically important since ancient times. Located between Siena and Arezzo, the small village is an extraordinary example of medieval town planning, set in elliptical concentric rings, which have remained intact over the centuries. Walking through the narrow streets, between houses of stone and brick, you will reach the heart of the village: the square of the Tribunal, which is overlooked by the 13th century Town Hall, Church of St. Francis and the Collegiata.

Inside the Town Hall building is the museum, which houses impressive works of art from the Tuscan Middle Ages and Renaissance. Among the treasures is the magnificent Golden Tree. Standing 8 ½ feet tall and richly decorated, it attracts visitors from all over the world.

The Casentino Valley is rich with history, art, great food and outdoor activities. Some of the places to see include the castles of Poppi, Romena and Porciano, the Franciscan sanctuary of La Verna, the monastery of Camaldoli, the zoo in Poppi and the small towns of Stia, Pratovecchio and Castel San Niccolò. The historic Poppi Castle is of particular significance. The Counts Guidi hosted Dante Alighieri in 1310 for almost a year and it is in this castle that the great author penned XXXIII canto of the Inferno of the Divine Comedy.

The little town of Stia is located at the meeting of the Staggia and Arno Rivers. Wool was the main industry in the valley and the Eco-Museum for Wool is worth a visit. At one time, the mill employed over 500 people. Stia still produces its “panno casentino,” which is a fuzzy wool cloth. You will find shops around town where you can buy winter coats made in the quite particular cloth; orange and green are the most popular colors. Like many of the villages that dot the Arezzo province, Stia has a charm that sometimes defies description, but like its wool, leaves you with a warm and comfortable feeling.