Cortona, Italy, is a quiet, cobblestone hill town with fun bars, beautiful lookout points and a unique ambiance that brought us back time and again. Here’s how you can enjoy it, too!
Famous for the book-turned-movie “Under the Tuscan Sun,” Cortona is a striking, scenic city that we fell in love with quickly. (Seriously, in the span of one week we visited at least three times.) The city’s exterior walkway offers expansive, jaw-dropping views of central Italy’s farms, vineyards, and hill towns. And, if you happen to stay in Cortona after hours, you get to experience quite possibly the city’s most spectacular sight: the sunset over Tuscany.
With this picture-perfect panorama outside city walls, it’s tough to pull yourself away and actually go explore Cortona’s interior. But you should.
Scratch that; you must.
Cortona is an enchanting maze of steep cobblestone streets, tall, hollow archways, bustling cafe-lined squares, and countryside views that sporadically pop up at the end of small alleyways.
While technically small, Cortona is a vibrant, spirited city with enough off-the-beaten-path nooks, side streets and crannies to keep you busy exploring for days. My family and I actually made two stops here while in central Italy because we couldn’t get enough Cortona!
Cortona City Exterior
In case I didn’t emphasize this enough, the walkway into Cortona is a must. It offers dazzling views of Tuscany’s lush, vibrant countryside, particularly during sunrise or sunset.
The walkway, which winds along the outside of the city, has several parks for a quick rest or some photography on your climb up to Cortona. (And trust me … when I say climb, I mean it. More on that later!)
Piazza della Repubblica
Remember those archways and cobblestone streets I talked about? This, my friends, is the place to find them. The Piazza della Repubblica — the main Cortona square — has a variety of shops, restaurants and cafes, as well as a commanding clock tower (Palazzo Comunale) and one of those surprise pop-up viewpoints I love, straight through the archway near the clock tower.
Like many Italian cities, the Piazza della Repubblica is a great place to sip a cappuccino under the (Tuscan) sun and soak up the city vibe.
Piazza Signorelli and The Lions Well Pub
While it’s not the main city square, Piazza Signorelli offers the same Cortona charm as Piazza della Repubblica, with fewer tourists and — wait for it — a pub. Yes, beer (good beer!) in the heart of wine country.
Across central Italy, we found that the younger Italians are doing their part to bring the beer revolution to a region historically known for wine, wine, all the time. Here in small-town Cortona, it was no different.
The Lions Well Pub has a typical hole-in-the-wall feel, and offers better beer than the typical Peroni. [Cue the applause!]
For me, it was Erdinger Weisse every time. Now, I know Erdinger isn’t an Italian beer, so I wasn’t experiencing the Italian beer culture per-se, but given we were the only non-tourists in the pub, watching soccer with the staff, it was definitely an Italian beer experience. (And as we saw at Lions Well – the Italians like their wheats!)
Stroll through Cortona’s Streets
Like most small Italian hill towns, the town itself is the sight. While Cortona doesn’t have big monuments or epic cathedrals, it has a magical culture that’s easily soaked up by exploring the town on foot. Walk through the alleyways, allow yourself time to get lost, and trust me – strolling in this manner will give you a much more local, authentic experience than any sightseeing “checklist” could do.
Know before you go
Like all Italian hill towns I’ve visited, this is another, well, hilly town. Plan your footwear ahead of time and wear layers you can shed because that uphill, sunny climb is a workout … and that downhill climb at sunset can get pretty chilly.
Looking for more Tuscany day trips? Check out Civita – one of my all-time favorite Italian hill towns!