Location — If you look at a map of Italy, Cortona is pretty much smack-dab in the middle. It is located between Rome and Florence, in the province of Arezzo, set on the side of one of the Tuscan hills covered in olive groves.
Population —The city is surrounded by high, stone walls and so its expansion is limited. There are currently around 23,000 people.
Cortona's Claim To Fame — American author Frances Mayes moved to Cortona, found love, and wrote a book called Under The Tuscan Sun. This book was turned into a movie of the same name which was filmed in the town. Cortona’s opera house made an appearance in the movie Life Is Beautiful and, on a more historical note, it is one of the few cities bypassed by Alexander The Great who apparently marched right by on his journey to conquer the known world.
Orientation — Because the city is built into a hill, it has only one level street, Via Nazionale or Main Street, located near Piazzale Garibaldi — the main gate. As I mentioned before, an ancient stone wall (going back to the time of the Etruscans) encircles the entire city and there are only a few exits or entrances. Most of the hotels, restaurants and cafes are located near, or just off, the Main Street. At the top of the hill is a huge cathedral and the old historical fort. You can walk around the entire city in about an hour.
Getting Around — There is no need to do anything but walk within the city walls. Most of the roads are very steep and made of uneven cobblestones, so make sure you are wearing comfortable footwear (leave the heels at home ladies).
Getting There And Away — The Florence-Rome train line does not stop in Cortona, but in Camucia located at the bottom of the hill; the stop is called Camucia-Cortona. It is close enough to both of the big cities that you can easily visit Cortona as a day trip (but I recommend staying at least one night). Buses, running every half hour, will take you up to Cortona’s main gate, BUT if you are up for it, a 20-30 minute walk through olive groves and past stone farmhouses is also an option.
Where To Stay — Ostello San Marco is the main hostel is the city and is located in an old monastery which means that it has huge, clean rooms. Their website is pretty rough, but it's where I stayed and is a fantastic hostel. There are a few small hotels and B&Bs as well.
What To Do — Though Cortona is small and not full of the usual attractions, what makes this place so special is the atmosphere. It has the feel, smells, and look of another time — everything that you imagine the idealized ‘Tuscany’ to be can be found within the city walls.
There are incredible views of the valley from multiple locations, bakeries full of treats, wine bars bursting with local flavours, and family-run restaurants full of melt-in-your-mouth dishes. There are also stunning examples of Renaissance architecture, churches with beautiful sculpture, and the Museo Diocesano has some incredible pieces (notable is a masterpiece by Fra Angelico).
A hike up to the 16th century Fortezza, originally built for the Medici family, is definitely worth the sweat, as it offers stunning views and a unique look at the interior of the fortified walls of the city.
How I Found It — My University had a campus located in Cortona, so in 2004, I was lucky to spend almost 4 months living in the city. While there, I studied art history, history, and classics from people who lived or worked in the area.
I went for morning jogs past Frances Mayes’ home, drank Tuscan wine daily, and became a regular at Bar Sport, my favourite cappuccino spot, where I learned the art of drinking coffee in Italy.
It is — without a doubt — one of the most magical places that I have ever been, and well worth the hike up the hill to visit it!