Eastern Tuscany: Arezzo and Cortona

It has been a while since I have posted, mainly because we had not traveled anywhere new for some time, and we returned to the U.S. in March for a few weeks, which distracted me from updating ūüôā

That being said, this and the next few posts will depict my adventures with my friend, Lauren, who came to visit at the end of February. Ryan and I picked her up in Florence and decided to start her trip on a one night stay in Eastern Tuscany, a region we had not yet explored.

Arezzo is one of those towns that escape the tourist map. While most people flock to San Gimignano and Siena from a day trip in Florence, many skip over this magical fortress of a city built by the Etruscans. It is famous for its medieval Piazza Grande, which houses Santa Maria della Pieve.

Our favorite spot was the Parco della Fortezza Medicea, a sprawling park with fountains boasting magnificent views of the Tuscan countryside. The town felt freshingly authentic, with many families and their dogs enjoying the mild and clear winter day. From there you can make your way to the Cattedrale di San Donato, which looms over the park with  immensity.



We had lunch at a wonderful little nook called Il Cantuccio, a favorite among locals and was not to disappoint. Lauren was impressed with her first meal, where we gorged ourselves on seasonal vegetables, minestrone, pici pasta, bruschetta, dessert, and local wines. The total bill for three people stuffed to the brim was under 40 euros. This would 30% higher in any tourist institution!


If Arezzo exuded old world charm, Cortona exceeded that charm while being perched on a steep cliff with unrivaled views. You may have heard of Cortona as the setting for the movie “Under the Tuscan Sun.” Because of this designation, I had read that it can be swamped with tour buses in the high season. In February, however, the town was vibrant with local Italians venturing into town for Sunday lunch & dinner. The road to Cortona winds up the mountain. You can catch glimpses of the town on top of the hill with growing anticipation, until you are greeted with a magnificent view of the countryside from the Piazzale Garibaldi¬†at the entrance of the town, which was also close to the famous church San Domenico.

We stayed at a 2 bedroom apartment in the center of town in a building that was as old as the city. Walking along the town at night, we were recommended a modern aperitvo bar for drinks, where we noshed on free appetizers and fruity cocktails that were western influenced, yet still delicious.


We then caught sight of the Piazza della Repubblica before heading to our dinner at¬†Ristorante La Bucaccia. Still stuffed from our lunch in Arezzo, ¬†Lauren and I had a light dinner of minestrone and gelato, while Ryan’s appetite led him to both a heavy cheese appetizer and steak dinner. Everything was excellent. The building had actually been the site of an old Roman road and there was even a spot by the bar where horses used to be held. It never ceases to amaze me how much ancient history can be found in the most ordinary places.


The next morning we set off on a walking tour of Cortona before heading back to our home. A ten minute walk through local stone roads led us to an opening by a cathedral. From there, we were surprised by a view of the Cimitero della Misericordia.


Our journey continued upwards towards the famed Basilica di Santa Margherita. Upon reaching this church lofted at the top of town, we were surrounded by a mass of people gathering for services, as well as food trucks selling candies and souvenirs to tourists. Even though this was quite off-putting, it did not take away our complete awe for this village. We did not make it to the Fortezza di Girifalco right above the church, but we were still able to admire its beauty from afar.

Cortona- thank you for a memorable visit and you will remain in our opinion one of our favorite towns in Tuscany!




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