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!