Tuscan Excursion Part 2: Exploring Pienza

When we told our hostess in Florence that Pienza was our next stop, we discovered she’d been born and raised there. “It is by far the most beautiful place in the world!” she told us. It was a bold claim, but once we arrived, I understood her affection for it. Pienza became one of the most peaceful and picturesque places I’d ever visited.
An exploration of timeless style, travel, and the art of living.
Exploring Pienza

Situated between Montepulciano and Montalcino, it is a gem of the renaissance era largely due to Pope Pius II’s involvement in the town (it is named after him). It lends most of its picturesque beauty to being in the Val d’Orcia region of Tuscany with its rolling hills and cypress trees that adorn the land.
Things to Do:
Pienza’s old town is small enough to explore in a few hours, but its laid-back atmosphere makes it worth taking your time. If you love Renaissance architecture, stop to admire the Duomo and its bell tower rising above the town. Wander into the alleyways and let the quieter pace become part of the experience.
Cyprus trees with views of the Val d’orcia
Pienza Storefronts
Homes in Pienza
The Duomo
If you’re a cheese lover like I am, this is heaven. All the cheese you can imagine is here with an assortment of meats. Makes for a great cheeseboard. This cheese shop has the pleasure of being the same one that was in an episode of the tv show (and one of my favorites) Master of None.
Take a drive through the Tuscan countryside and give yourself time to stop along the way. From town after town, the views seemed to have been plucked from a painting. It was hard not to be amazed by the landscape around us.
Where to Eat:
Al Fierale was a welcome place to end a long day of exploring. The food was excellent, particularly the meat, and the Pecorino di Pienza was worth the price. It was lively inside, so we chose an outdoor table where we could relax after a long day and enjoy a quiet meal. I’d happily recommend it for dinner.
You’ll notice gelato makes quite a few appearances in this journal. Every town that you arrive at will have someone seeking amazing tasting gelatos. A friend of ours recommended this gelato spot to us before coming to Italy, so we had to make sure to check it off of our list. This was one of the best locations—a nice treat to have whilst exploring the town’s limits.
List of Additional Restaurants in Pienza
Where to Stay:
During the planning of this trip, I was looking for the best small town that could be a springboard for all the other small towns in the area. Pienza came highly recommended and I’m glad we decided to stay in this gorgeous town.
We found a private villa in Pienza that we had entirely to ourselves. A Dutch painter had loved the place so much that he returned repeatedly to paint the view from its main window. The owner was welcoming and accommodating, and a cat kept us company during our stay. She was great company.




