Cortona was forty miles northwest of Montepulciano, which seemed like a long way to drive when I was planning the trip. I might not have included it at all if it wasn’t for the glowing descriptions in “Under the Tuscan Sun”, essential reading for anyone planning a trip to Tuscany. Now that I’d had the opportunity to experience some of the scenery and set the GPS to avoid major roads, I didn’t mind long drives at all.
Unlike the other medieval cities we had recently visited, Cortona spilled across the side of a hill rather than occupying its crest. Once we had snaked up the switchbacks to the edge of the old town it was surprisingly easy to find a free parking spot. We entered via the Porta Sant'Agostino and walked up a flagstone-paved street that was completely deserted. It seemed at first that we had entered a giant ghost town.
The atmosphere changed as soon as our street connected with Piazza della Repubblica, Cortona’s main square. The spacious plaza was far from crowded but there was a pleasant buzz of activity around the cafes and small shops that lined the periphery. The square is dominated by the medieval Palazzo del Capitano which provides an imposing backdrop for anyone enjoying an apertif at one of the outdoor tables of the Enoteca Molesini on the south side of the square. The wine shop has been refreshing visitors to the square since 1937. The wide staircase in front of the Palazzo is a popular space to meet and hang out. The grey stone building features two beautiful archways, one at the center and one to the side, and is currently a residential building. Not a bad place to have an apartment! A smaller building of similar grey stone faced toward the Palazzo from the opposite side of the square. A large white bust of a man with mutton chops and a military uniform was affixed to the facade of the second level. Cleo asked me to identify the man and I told her he was Justin Bieber, enormously popular in Italy. Justin's no longer a tween idol so Cleo had to think carefully before determining that I was tormenting her.
Several possible routes emanated from the piazza but the obvious choice was the main pedestrian street, Via Nazionale. This was the central artery of commerce in the city and was filled with salumerias, bookstores, restaurants, gelaterias and all the other beloved accoutrements of Tuscan hilltop cities. The narrow street felt like a canyon with the tall stone buildings on either side providing shade to throngs of visitors browsing through the shops or having a drink outside. Via Nazionale was also notable for its preponderance of art galleries, the highest concentration we had seen since Pietrasanta. We passed several with their doors invitingly propped open, leading to hallways decked with colorful paintings. I couldn't resist one ancient entryway with crumbling stone walls and an upsloping floor that led to a cavelike interior. On the walls were hanging dark-hued, cubist canvases that seemed to complement the foreboding, medieval atmosphere. I rounded a corner and found myself in an artist's cluttered studio where an elderly, slightly disheveled man peered at me curiously. This proved to be Luciano Radicati, the creator of the paintings that had drawn me inside. We had one of those short, slightly awkward conversations typical of people without a common fluent language, making do with a pastiche of English, French, and Italian. It seemed not many of Cortona's visitors found their way to his studio because he was eager to explain his work but there really wasn't much I could understand. I tried as best as I could to communicate that I appreciated his artistry and then rejoined my family outdoors where they were finishing off their afternoon gelato.
At the end of the old town Via Nazionale spilled into a confluence of modern roads. On the south side of a traffic circle called Piazza Garibaldi there was a belvedere overlooking the Val di Chiana and the roof of the Santa Maria delle Grazie al Calcinaio church. We retraced our steps back towards Piazza della Repubblica, this time keeping an eye on the narrow alleys that snaked up the hill to the quiet, residential areas of the town. Part of the reason for Via Nazionale's commercial success is that it is one of the few streets in Cortona that traverses level ground. The even narrower vicolos that emanated from it perpendicularly all required navigation of staircases. We selected the most promising of these and soon had left the bustle of Via Nazionale behind.
As we ascended further the slope of the hill diminished and the stairs gave way to inclined flagstone streets. There were only residential buildings here whose impeccable wooden doors contrasted with their timeworn stone facades. We encountered no one else during our ascent, with the only sign of contemporary life being the occasional gleaming car parked in some convenient nook next to a medieval building. The wide stone staircase in front of the San Francesco church was quite similar to the one belonging to the Palazzo del Capitano.
Eventually we made it to the overlook, marked on Maps as Il Bucco del Culle. I have no idea what this is supposed to mean as the closest Italian word to bucco is buco, which means hole, and culle is the plural of cradle or baby cots. Il Buco del Culo would mean asshole so perhaps someone with limited Italian capabilities played a practical joke on Google. It wouldn't be the first time. We could also see some remnants of an ancient outer wall of the town.
If I had been on my own I might have continued hiking upward to the crest of the hill to see the layout of the city from above but it wasn't feasible with the kids, especially considering the remaining sites I wanted to see on the periphery of Cortona. Instead we took an alternative route back to the center that brought us to another square that I initially confused with Piazza della Repubblica. This was Piazza Luca Signorelli, named for the Renaissance master who hailed from Cortona and whose frescoes can be seen in a number of historic buildings around the center. The building that stood out on the square was the neoclassical Teatro Signorelli, fronted by a spacious loggia. The theater has been the major venue for performances and cultural events in Cortona since the sixteenth century. From here a short passage brought us alongside the Palazzo del Capitano back to the Piazza delle Repubblica.
We could have walked to the Fortezza del Girifalco just outside of the town in about twenty minutes but the kids were already tired and taking the car was so much simpler. The road brought us first to the Basilica of Santa Margherita where I parked, confusing the church with the fortress. Santa Margherita is the patron saint of Cortona and the fourteenth century church built to memorialize her has been reconstructed and enlarged several times. The existing nineteenth century facade features three intricate Gothic rose windows.
The fortress was just a short drive uphill from the basilica. It didn't look particularly fascinating from the outside but since we'd made the effort to drive there I sprung for admission for the five of us. Inside there was a grassy courtyard with an incongruous display of erotic photography on the walls, which the kids ignored. The staircase leading to the battlements seemed to be closed off and we had to take an elevator on the inside of the building to the third floor. Here there was a rather gruesome exhibit that had a theme of death, with photographs of murder scenes from Depression-era New York City and some before-and-after photos of terminally ill people who had died. For some reason the kids did find this fascinating and it took some coaxing to get them out onto the battlements. We could look down at the courtyard we had been in earlier and the featureless interior stone wall of the fortress.
We had our best views yet of the Val di Chiano but after so many overlooks here and in Montepulciano we had our fill of the familiar patchwork of green and beige. The only difference here was that I could see Lake Trasimeno, where I was planning to take everyone next for a swim and then dinner.
Our last stop before leaving Cortona was the Convent of Le Celle, a slightly further distance from the town. The last part of this drive was rather discomfitingly narrow and rocky but it was worthwhile as the convent was quite beautiful. According to local history the site was chosen by Francis of Assisi as a hermitage because of its isolation. After Francis's death it was expanded into a sanctuary and then centuries later it was taken over by the Capuchins who built it up substantially. The convent is open to religious visitors who seek a place to pray and enjoy the company of like-minded individuals. We stood above the main building that houses the monks and visitors and shielded our eyes against the sunlight in order to appreciate its remarkable structure and beauty. It didn't seem advisable to try to explore further as the kids were rather boisterous and we didn't want to disturb the scene of tranquility.
As we were leaving Cortona behind the kids announced they weren't in the mood for a swim after all, but I decided to head for Castiglione del Lago anyway. I thought a small town by the lake might be an ideal environment for dinner. I didn't know anything about the town but I figured it would be a typical flat, laid back place where we could have a stroll by the lakeside before dinner. I was quite surprised when we arrived at the town center and found another hilltop citadel with a tall stone wall sharply demarcating it from the surrounding modern city. One of my most beloved features of Italy is that virtually any town, even those well off the beaten track of international tourism, can turn out to be a spectacular discovery. Lake Trasimeno overall is largely ignored by travelers despite being the fourth largest lake in Italy. It contains two inhabited islands and there are several old cities along its circumference. It could have been the setting for several days of leisurely exploration but our itinerary only allowed us the one evening in Castiglione.
The cigar-shaped citadel occupied a ridge at the top of a promontory extending a few hundred meters into the lake. Just two parallel streets coursed lengthwise through the town with most of the restaurants and shops lining Via Vittorio Emanuele. There was only one piazza in the town but it was quite pleasant with a central fountain and an old clocktower. The clocktower seemed to have been shored up by newer buildings placed alongside it.
Despite its small size, the citadel had all the features that make historic Italian cities such a pleasure to meander through. Reflections off of glass jars and cellophane packaging signaled that we were passing a gourmet food market that doubled as a cafe. Next door were the thick and imposing columns of the nineteenth century neoclassical Church of Santa Maria Maddalena.
About halfway along the length of the citadel Via Vittorio Emanuele ended at a traffic circle. The remaining section of the ridge that projected lakeward contained the sixteenth century Palazzo della Corgna, featuring Renaissance architecture and contemporary frescoes, and the medieval fortress Rocca del Leone. The fortress is most remarkable for its triangular lookout tower and the movies that are screened in the courtyard on a regular basis. The area between the Palazzo and the fortress was occupied by Castiglione del Lago's main hospital.
By this time we were whizzing through the remainder of the citadel as quickly as we could, trying to absorb all the sights of the old town before the evening dinner rush. We hadn't passed any restaurants that seemed outstanding so I did a quick search and came up with Squad Garden, an unappetizingly named place with good food ratings and a claim to a lake view. Maps directed us to the ground floor of the building that the restaurant occupied, at the base of the wall of the citadel, instead of the correct entrance in the old town. Inside we found an elevator that ignored our calls and no staircase. The kitchen was next to the elevator so after some minutes of waiting we gingerly walked in and found a staff member to call the elevator, which required a key. He advised us that the elevator door might not open at the top but he would wait at the bottom and we could press the alarm should we become trapped. Fortunately that didn't occur and we were able to make it to our table. The food turned out to be very average and the lake view was likewise unimpressive, but we were relieved to have completed our final obligation of a very long day. We took one last spin through the old town now that it was dark but it was clearly not a place that became more lively after sunset. We descended the hill to our car and drove half an hour back to our Airbnb in Montepulciano.
Once again there were a couple of open free spots with white stripes at the paid parking lot just outside the Porta al Prato in Montepulciano. We figured that they filled up early in the morning with the cars of workers from the neighboring towns who left in the afternoon or evening. The bulk of the tourists who drove in during those hours probably never grasped that the lot inexplicably contained about ten free spots and assumed that it was safer to just park between blue lines and buy a ticket. It wasn't much money compared to everything we had already spent but it's always a boost to get something for free when we travel. It was fortunate that we had an Airbnb host who had been considerate enough to point this out to us.
This featured blog entry was written by zzlangerhans from the blog Fledgling Explorers.
Read comments or Subscribe
Recent in Family Travel
- Il Dolce Viaggio: Cortona
- Il Dolce Viaggio: Pitigliano
- Sailing around the Saronic Islands
- To the Infinity Pool and Beyond: Muscat
- China Deep Dive: Hangzhou
- China Deep Dive: Chongqing arrival
- Two degrees and snow were waiting for us
- China Deep Dive: Chengdu
- Ponte Tresa
- Down time in Graenichen between Colmar and Ponte Tresa