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Mar 12

Towns in Tuscany: entering the living painting of Italy

The winding roads, rolling hills and picturesque views of Tuscany

Many destinations across the world compete for our attention. Some places are as spectacular in person as their fame claims to be, while others may be overhyped. One destination which certainly lives up to its hype is the charming countryside of Tuscany. Set in the historical and pure landscape of central Italy, this destination has been a constant attraction for romantics, nature lovers and travelers for years. The best way to describe the peculiar beauties of this landscape is to think of journeying inside a painting. If you’ve ever looked at a painting that portrays a landscape that seems to be out of this world, something so powerful that it seems to actually capture your imagination and bring you to that place, that is the kind of landscape that Tuscany is. Just physically being here is not the only thing you feel, you feel like you’ve been picked up and dropped inside the vivid canvas of a master painter.

There are many cities and towns to explore in the Tuscan countryside and one should not expect to reach them all even on a lengthier trip. In fact while the hillside towns and medieval structures are fascinating adventures one can easily and successful spend one’s days driving the countryside, heading down old dirt roads in search of breathtaking views of old farms, tree-lined driveways with picturesque villas and curving roads which wind along hillsides covered in the brightest colors of nature. A trip to Tuscany can encompass some well-known favorites like Florence with its museums, art and graceful streets; Siena with its summer festivals and resplendent architecture or Pisa with its iconic leaning tower. While these cities are great destinations in themselves and are by all means noteworthy, the focus in this article will be on two smaller, but equally as fascinating towns: Arezzo and Cortona.

Even when I’ve described a place that sounds otherworldly, it is very much geographical and takes some planning to arrive. This is not a typical international city destination. One can fly into Rome or Milan and make their way into the countryside or even fly to Pisa or Florence, but still there will be efforts to move about. Since Tuscany occupies a hilly and mostly rural area, it is helpful to rent a car or have a good knowledge of the local bus and train options to get from town to town. The benefits of having a car are immense, since this affords one the freedom to explore smaller roads and stop wherever one would like to embrace the exquisite scenery.


The artesianal shops of Arezzo

The great thing about Tuscany is that every place has its own special character and unique appearance. This holds true for the first stop on this journey in the town of Arezzo. As is typical of many of these ancient towns it is set on a prominent hilltop with a well-preserved medieval quarter. The modern outskirts of the town are in a flat area where much of the local industry is now located. As one approaches the historic center the first signs that one is crossing a unique threshold comes at a well-preserved ancient city gate. The streets all at once begin to climb the hillside. Even when the towns goes up the hill quite a ways and offers a prominent view of the surrounding area, the grade of the incline is not too steep. The streets are wide and splendid. There are many churches around the city which house a great many works of art and are built-in a range of styles. It is easy to see how this city was a bastion of wealth and prestige in its medieval heyday. The facades of many grand palazzo grace the city and the streets are often full of families and tourists exploring the many chic clothing stores and rural themed stores which sell choice local products of meats, cheeses, wines and produce. These places are visually attractive and even if that fails to lure one in, the pleasant fragrances of fresh food will entice even the most skeptical buyer.  The prices will be more elevated than a typical grocery store but the quality of the products is unique and exquisite. Continuing up the slanted streets the agile tourist will pass curious structures like the Santa Maria delle Pieve church with its peculiar shape, well-carved fascade and unique bell tower.  Continue following the hill or the crowd towards the main center of the ancient city for its most astonishing views.

The most notable area of the town strikes the visitor with awe when one arrives to Piazza Grande. This open area of grand proportions is a gently sloping square full of fountains, massive palaces and quaint little apartments adorned in local hues and complete with hanging ivy and plants. This is the former marketplace of the city and it certainly is a place to enjoy a well-deserved rest or a refreshing coffee on the Vasari loggia terraces. The square is certainly one of the more scenic and memorable in Italy and even more so due since it served as the setting for the classic Roberto Benigni’s 1997 award-winning film: Life is Beautiful. The majestic designs on the stonework of the square mixed with the wonderfully preserved medieval architecture creates an enjoyable atmosphere for tourists and for fans of the film it is a special moment to re-experience all the touching emotions that the film elicits.

The picturesque hills of Tuscany

Continuing uphill, one can arrive to a scenic park, which overlooks the Romanesque churches and labyrinthine streets of Arezzo. It is a great place to take in fresh air, exercise and enjoy the leisure time of locals. Many come here to appreciate the views and share a drink at some café’s on the edge of the park. The park on its eastern side also has compelling views of the greater Tuscan countryside. Just next to this area of lush pines and fertile lawns is the large and impressive Cathedral of St. Donatus. This church is built in a typical grand Tuscan-Gothic style. This usually consists of large churches made from very huge stones on the outside, which are usually brown, reflecting the same type of soil cover that dominates most of this region. The churches are often very hollow and spacious inside but spare no cost in adorning the many altars with great paintings and sculptures.

As one exits the town it is best to go by side streets if possible. This is not too out-of-the-way since all small streets often lead back to the main causeways. This can be a great way to take in the unique homes built into the hillside and see their decorative balconies, colorful hues and delightful lampposts. Arezzo is a unique town with a long and colorful history. It is the perfect place to enjoy a medieval city of astounding beauty, modern fame and it is a great adventure into Tuscan leisure.


The serene structures of Cortona

Only a half hour or so from Arezzo one can easily arrive to the city of Cortona. Similar to Arezzo this city is as well-built on a hill, yet the hill is a bit more inclined and with narrower streets than the previous venture. The town like many others in the region has pre-Roman foundations and some of the Etruscan (a group in power here before Rome) walls are still visible in parts of the city.  Just like Arezzo it is situated in the Val di Chiana area and represents some of the most important patrimony of art and architecture of this corner of Tuscany. The town may also be familiar to book and film gurus as the setting for Francis Mayes Under the Tuscan Sun and it rightly lives up to its fame for being a place to enjoy life in some of nature’s finest settings and culture.

Just arriving to the town will be quite a trek up the hill for any vehicle. There is ample parking on some of the side streets just near the city center. As one enters the city the first area to approach is a small square called Piazza Garibaldi with a commanding view of the valley below. The plains are decorative with great tones of earthy colors, from bright greens, to dark pines to rich, brown earth. In the distance one can see the beginnings of the large, volcanic lake Trasimeno. From here simply take the main road Via Nazionale to pass through the heart of the city. It should be noted the city is really arranged in layers, so a walk from one side to the other in Via Nazionale will only take a few minutes, but it captures the main aspects of the town. Should one wish to get a look at the package, there will be quite a bit of stair work. Most of the streets and intimate passageways offer pristine views of the mountainside as well as unique homes from all different eras worked into the mountainside.

The main street boasts a great many antique stores, cafes and enotecas. This is a very typical Italian shop, but it can be best experienced here in the Tuscan atmosphere. The shops will often have a great display of Tuscan and other wine varietals in the front. Towards the back is often an ancient area with a very cool temperature set in a rustic, home-like scene. Often the ceiling is a blend of arched brickwork and tables and chairs are simple wooden setups with no pretense. This is not a full-blown restaurant, more a mix of a wine bar and sandwich shop. One such place here is Enoteca Enotria. The menu has a great choice of local wines and the snacks and sandwiches are typical Tuscan meats, cheeses and oils hand-made for a delicious and sumptuous immersion in the bounty that this region has to offer. As one continues down this street the passageways broaden enough for a couple of stately palaces, such as the Palazzo Communale, administered by the current government. These buildings are fascinating medieval structures that often have family and king’s crests carved into the outer wall, which tell the stories of war and conquest in these hills in the not too distant past. The town also has a remarkable art gallery, which features some amazing talent which captures the local terrain. The paintings are not only truer than life, but the blend and vivacity of their earthy colors are something equally as beautiful as the iconic Tuscan hills.

A short ways to the end of the main street one can reach the local cathedral. It is an impressive structure filled with ancient and modern works of great fervor and piety. The greatest treasures in art for the town and the church lie in the diocesan museum. Besides some other works, which are recognized in their own schools and periods, the masterworks on display here are three paintings by Fra Angelico. The medieval monk is famous for his scriptural scenes and his most famous portrait known as the Annunciation lies here is this beautiful and historical town. Other places of interest outside the main are of town are the celebrated fortress of Gilialco, the noteworthy hermitage le Celle and the Melone of Sodo Etruscan tombs. Cortona is another fine example of the noble and artistic feats of man, which correspond so reflectively to the astounding beauty of Tuscany.

There is so much one could continue to relate about the stunning art, architecture and beauty of Tuscany. Perhaps more than being seen, Tuscany is a place to be experienced. Everything from the typical landscape, to the mouth-watering food, to the clean air, colored hills and outstanding towns. It really is the masterwork of two great artists, nature and man. The canvas of nature is stunningly picturesque and inviting while the creative design of man is the shaping of towns, villas and farms all of which reflect the serene tranquility and romance of this Italian landscape and culture. So, be sure and have a look at this immaculate landscape for yourself and be careful, you may just find yourself in a living painting that you don’t want to step out of!





This is the Editorial Board of The Joys of Traveling. We are passionate travel writers who seek to provide objective and accurate accounts of travel experiences by means of written articles, photos and videos.


  1. Joseph Cutis

    Certainly a great article of an amazing destination. I really should go to Tuscany some day. Thanks for sharing all this valuable information!

  2. admin

    Our pleasure Joseph. Tuscany is a wonderful destination and there’s so much to discover.

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