As impossible as it is to choose, Cortona just might be my favorite Tuscan town. I say “might” because even I can’t make a decision. Cortona checks a lot of boxes: stunning views, a piazza with a clock tower, amazing Italian food with local wine, aperitivo on an outdoor patio. Undoubtedly, one day in Cortona would include all of the above.
Naturally, this town has been on my bucket list since I first saw Under the Tuscan Sun. I’ve been to several places in Tuscany and Cortona really stands out.
While you could see the town in just spend a day, I chose to stay the night at Borgo Il Melone. This hotel is a good choice for the pool, easy parking and close proximity to Cortona’s town center. While the small economy room I booked was simple and the price was right (about 70 euros for a single in peak season). The service was friendly, the breakfast was quality and the pool was just what I needed on a hot day.
After an afternoon by the pool, I went into Cortona for the shops, aperitivo and dinner. I grabbed a glass of wine at a place in Piazza della Repubblica. Not to get to cliché on you, but this is where it’s at… la dolce vita. Some of my fondest memories of Italy are relaxing in a piazza and just people watching with no particular thing on the agenda.
A day in Cortona wouldn’t be complete without a proper Italian dinner. It was hard to choose where to eat, but I decided on Locanda Al Pozzo Antico. I don’t think there’s been an antipasto plate I’ve enjoyed more. It’s here I was first introduced to the wonders of persimmon with ricotta. Alfie, my dog was welcomed and we sat in the quaint outdoor courtyard. I made small talk with the owner and he mentioned seeing me with Alfie in the piazza earlier. Fellow celiacs, rejoice. Locanda Al Pozzo Antico serves gluten free bread and pasta.
Villa Laura is where they actually filmed Under the Tuscan Sun in Cortona and I quite enjoyed looking at photos of the property. You can rent the whole villa! The actual home of author Francis Mayes who the book/film is based off is also near by.
Now if only we could have all this with the cheese from Pienza, the wine from Montepulicano and the gelato from San Gimignano. Then we’d really have a Tuscan town that checks all the boxes. But, I guess now we’re just being greedy.
Read Next: Top Towns you Can’t Miss in Tuscany
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