Our favourite hilltop towns in Tuscany

There is something so liberating about jumping in the car and exploring; and regional Tuscany is the perfect place for it. Vineyards, olive groves and sunflowers for miles, you feel like you’re driving into a postcard. Not even driving manual on the wrong side of the road could put a damper on the freedom we felt cruising around.

Every day we ventured somewhere new but these hilltop towns deserve special mention (don’t bother visiting the lake though, it looks pretty from a distance but radioactive up close).


Perched high in the hills of Chiana this charming town invites you to linger. Cortona, the cultural and artistic centre of the Val Di Chiana region should be more showy than it is. It lacks the dirty ‘tourist trap’ vibe we’ve experienced in neighbouring towns; it felt authentic and calm.

If you’ve been following along you’ve probably come to expect us to feature food in some shape or form at each location we visit, so here it is. We started our tour of Cortona with Pecorino Pesto pasta (they had GF pasta and it was amazing), followed by coffee and a custard filled pastry.

We strolled the streets and stumbled across the most beautiful church with a timber raked ceiling. A refreshing contrast to the ornate, embellished churches we’ve come to expect in Italy.  Like the rest of Cortona it seemed paired back and modestly beautiful, which drew us in even more.

Art lovers can explore the free art exhibits on display from local artists and admire the sculptures that are scattered around town.

The drive down from Cortona offers stunning views of Tuscany. Just hope you don’t meet a car coming the opposite direction, the road has a sheer drop off a steep cliff.


Oh Sarteano you gem. We loved this sleepy little town. Boasting a medieval castle, charming streets and amazing restaurants you would expect it to be filled with hoards of tourists but when we arrived at lunchtime it was empty. It felt like we had stumbled on a deserted village, so we explored and sticky-beaked around, we could have been in the town completely alone except for the wafts of pasta sauce we could smell drifting out terrace windows.

As we made our way out of the town walls we heard the revving of a car, we turned the corner to see an old Italian man reversing out of the smallest garage we’ve ever seen. He jumped out of the car at started screaming at the wall behind him. Such an angry little man, it was hilarious; how dare that fucking wall get in his way.  Ah the Italians, never change.


The home of Pecorino Cheese and UNESCO World Cultural site is the reason we came to explore Tuscany after we saw the town feature in Master of None. The town is gorgeous but either we built it up too much in our minds or the number of tourists turned us off but it didn’t meet our high expectations.

Pienza is beautiful, the views from the town are stunning but it’s filled with foreigners carrying big cameras standing in the way of every cool photo you want to snap.

We gave up being tourists and defaulted to what we’re good at – eating. We ordered an antipasto platter from Salumeria Bernardini Laura and tried four varieties of Pecorino and I’ll give Pienza this much, they make damn good cheese!

I know I’ve said this before BUT we had the best gelato ever at Buon Gusto sure I may be fickle but mate this creamy goodness way to die for and I would go back to Pienza purely for another scoop.


Pretty, yes. Overrun with tourists, you bet! Montepulciano was the first hilltop town we visited so we thought it was amazing…Charming, great food, good photo opportunities. It had the lot. Until we explored more of the region and discovered there’s better. Kind of like my relationship with gelato.

We will be back in Tuscany tomorrow, so if you have any suggestions on amazing hilltop towns let us know.