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Cortona - Narrow streets

Cortona

5.0(5 reviews)
22.9 km

What a beautiful city. Narrow streets, barely wide enough for cars -- of course this village…read morepredates the Romans and is at least 3000 years old with parts of the Etruscan walls still standing. Cortona is built on a hilltop. There are no flat streets. Parking space is limited in the old city. The central squares host street musicians and markets on certain days. So picturesque with views forever. Beautiful buildings and restaurants where you can enjoy the mild Tuscan weather and shopping available. Made popular by the movie Under the Tuscan sun.

2009. We pedal up to…read moreCortona, another medieval Italian town that sits on top of a hill. The road up is a steep serpentine that never stops serpentining. We push on, each switchback like another cruel demonstration of the defensive advantage of building a town on top of a fricking hill. Cortona and its environs is where 'Under the Tuscan Sun,' Francis Mayes' insanely popular 1996 memoir about renovating a farmhouse in Tuscany, is set. The book was then adapted into an equally popular movie that was also shot around Cortona, though the plot was jazzed up, Hollywood-style. Instead of a memoir of a couple college professors doing a gut rehab, the movie is about a San Francisco writer who finds out her husband is cheating on her, so she moves to Italy and buys a run down villa and, you know, slowly repairs the house and her broken heart. The book + movie turned Cortona into a pretty serious tourist destination. More than that, it turned it into a fantasy destination. A place you can go after your life falls apart to find good food and laughter and a significant other with Hollywood looks. In other words, a place you can find in your guide book and reserve a hotel room in, but that doesn't actually exist.

Photos
Cortona - Looking down into valley

Looking down into valley

Cortona - Square

Square

Cortona - Square

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Square

Palazzo dei Priori - landmarks - Updated May 2026

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