If you’re searching for the most picture-perfect Tuscan town, look no further than Pienza, Italy. With gorgeous views, stunning architecture, and food that will leave you dreaming of more, it’s a must-see spot to add to your Tuscan itinerary.
As someone who lived in Tuscany for over a decade, I have visited my fair share of countryside towns, including Pienza. And, now that I am a travel planner who curates itineraries to Italy, I often have travel clients ask advice on where to visit in the Tuscan countryside. Here, I’m sharing where Pienza is, what it’s known for, and things to do when you visit.
Where Is Pienza Italy?
Pienza is located in southern Tuscany, 30 miles or so south of Siena, in the postcard-perfect backdrop of the agricultural area known as Val D’Orcia (pronounced “Vahl Door-cha”). The valley has a unique landscape of flat plains, rolling hills, and cypress-lined roads. So, it competes with Chianti for being one of central Italy’s most picturesque wine regions.
Get To Know Pienza
The town was built under the direction of the Tuscan humanist Enea Silvio Piccolomini. He was born in Pienza in 1405 but eventually outgrew his small-town origins and became Pope Pius II. Under his pontificate, he decided to change the name of his hometown from Corsignano to Pienza (after himself), and he tasked an architect to restyle the entire city.
Pope Pius II’s idea was to make Pienza an ideal town with harmonious dimensions and meet the ideals of Renaissance humanism, which placed beauty and symmetry above all else.
Why Visit Pienza Italy?
Pienza is a dream location, and we send our concierge travel clients here since it has incredible food, wine, and history. But also, if you’re traveling between Florence and Rome, it’s a countryside spot where you can spend a long weekend getting away from the bustle of the cities and experience another side of Italian life.
Walking around Pienza is like stepping into the Renaissance. The city is nicknamed the “ideal city of the Renaissance since it’s a perfectly preserved example of Renaissance architecture.
Today, it’s worth visiting just for the beauty of the architecture alone, but its perfection truly doesn’t stop there. Pienza has some of the best views in Tuscany. If you’re looking for postcard Italy, Pienza is the rolling green hills, cypress-lined roads, and small castles in the distance.
Beyond the views, don’t miss tasting Pienza’s famous Pecorino di Pienza cheese, sampling Cinta Sinese pork products (produced from pigs local to Tuscany), and sipping on a glass of red wine from the neighboring Montalcino.
What Is Pienza Known For?
Pienza is a great town for everyone from young to old, art lovers to food lovers. The wide, carless main street makes it a stress-free place for kids to run or for couples or friends to walk freely.
The history and architecture will please any history buff, and the food, especially the pecorino cheese, is famous worldwide.
Photography lovers will fawn over the historic walls and town center views. Many photographers enjoy taking pictures in the Via dell’Amore, the love street, or sharing a kiss under the sign for Via del Bacio, the kiss street.
Taking a stroll down the main street, then looping around the edge of town following the historic walls, is breathtaking and relaxing, and the wide, flat streets are perfect for pushing a stroller or even a wheelchair.
What To Do In Pienza?
In addition to history and architecture, the town of Pienza has so much of what we adore: chic independent shops, stylish boutique hotels, and a mix of restaurants and bars where you can sip local wine or get a craft cocktail.
It’s also a perfect jumping-off point to explore the area. Many of our clients spend three to four days. Hence, they have time to experience the thermal baths in Bagno Vignoni, do a farm visit to learn about craft cheeses and olive oils, or spend a day exploring the celebrated wines of the area like Brunello di Montalcino and Vino Nobile di Montepulciano.
Most wineries offer tastings and tours by appointment — head here to contact us if you need help organizing a winery day trip.
Six Things To See In Pienza
If you’re convinced Pienza needs to be on your list of must-see places in Tuscany, be sure not to miss these six things while you’re in town.
Piazza Pio II
It would be easy to arrive in Pienza, take a quick stroll, and head out. However, you would be missing the heart and soul of the town. Piazza Pio II is where Pope Pius II began creating his vision for this town, and all the buildings are built off of it.
It was designed using perfect proportions, meaning it is perfectly measured down to the centimeter to be symmetrical and linear. This is supposed to create a calming effect on those who visit, so take a minute to stand in the middle of the piazza and feel the effects of a perfectly designed city.
Pienza Cathedral
Don’t miss a chance to pop into Pienza’s small but beautiful duomo or cathedral. According to UNESCO, the Duomo work began in 1459 and quickly became one of Italy’s most important Renaissance buildings, as its facade was copied many times throughout Italy.
The church was built on the ruins of an ancient Romanesque church, and today, it houses many important Renaissance sculptures and paintings. Pope Pius II wanted those entering the church to feel they were in a building built of glass, not stone, and the light and airy atmosphere is truly something you must experience in person to understand.
Pecorino di Pienza Cheese
Stop into an Italian cheese shop or caseificio, and sample the famous aged cheese, pecorino di Pienza. This sheep’s milk cheese is made from sheep that pasture just below Pienza’s historic walls. It gets its special and notable flavor from three wild herbs that grow in these grassy hills outside of Pienza: artemisia, barback, and minstrel. The sheep’s diet, rich in these three plants, creates a unique flavor to the cheese that can’t be found anywhere else.
If you’re in the region on the first Sunday in September, stop by the “Fiera del Cacio” — a cheese fair highlighting this local pecorino cheese and which includes a cheese wheel rolling contest!
Palazzo Piccolomini
Visit the grand palazzo Piccolomini and taste how Renaissance popes lived. According to UNESCO, building began in 1459 by Pope Pius II, and he dreamed of a magnificent place to be suitable for himself and his cardinals.
Palazzo Piccolomini is exactly that, boasting a renaissance facade and an impressive rooftop garden (the first of its kind!) overlooking the Val d’Orcia. Inside the palazzo, you can visit the pope’s bedroom, library, and great hall, all of which have been meticulously preserved in their original glory. Bonus for movie buffs, the Italian film Romeo and Juliet by Zeffirelli was filmed here!
Corso il Rossellino
This main street was named after the architect Rossellino who redid the entire town under Pope Pius II’s direction. It cuts the city in half from entry to exit and is where most shops and restaurants are located. It would be hard to miss this street, as it’s the town’s main artery, but it’s worth exploring all it has to offer, diving into various shops while you stroll around town.
Gladiator road
Technically just outside Pienza center, but only 12 minutes by foot, you can walk along the stunning twisting dirt road made famous in the film Gladiator. This winding road is flanked by cypress trees and wheat fields, with a farmhouse in the distance.
If you’ve seen the film, you’ll recognize it right away as the place where Russel Crow walks longingly toward his wife and son. It’s classic Tuscany vibes and is also super easy to find just by mapping Pienza and searching “Gladiator road.”
Know Before You Visit
We always try to introduce you to places with a deeper cut, and we’re all about avoiding classic touristy mistakes and skipping the uber-crowded spots. Pienza is by no means unknown, but it checks all those boxes. Naysayers will tell you there are crowds during the day in midsummer (and they’re right), but we don’t think that’s a reason to 100% skip it. Rather it just requires you’re strategic when you travel there.
Since this is an agricultural area, we think the best time to visit is in the fall when grapes and olives are being harvested, and there are various local festivals to celebrate the bounty.
How To Get To Pienza, Italy
Pienza, perched high up on a hill, is easiest to reach by car. Bus service from Siena can be erratic, and the town has no train service.
Once you arrive by car, ample street parking and a paid car park are outside the historic walls. Then, it’s just a short walk from the car park to the middle of the historic city center, making visiting easy. Also, depending on where your Pienza hotel is located, they may have parking on site. FYI, some of our favorite luxury hotels in Tuscany are close to Pienza so you can stay there too!
Frequently Asked Questions
Pienza is renowned for its historical and architectural significance, being one of the first examples of Renaissance urban planning. It's famous for its picturesque streets and squares, the Pienza Cathedral (Duomo di Pienza), and Palazzo Piccolomini. Additionally, Pienza is celebrated for its production of Pecorino cheese, a delicious sheep’s milk cheese that is a staple of the region's cuisine.
The best time to visit Pienza is during the spring (April to June) or fall (September to October) when the weather is mild and the crowds are fewer. These seasons showcase the Val d'Orcia's landscape at its most beautiful, with blooming flowers in spring and harvest colors in fall. The summer months can be pretty hot and crowded but offer the chance to see Pienza at its liveliest.
It takes about 2-3 hours to drive from Florence to Pienza (about the same amount of time it takes from Rome to Pienza, FYI), so it is technically doable as a day trip from Florence. However, we think that will lead to a very harried day. Instead, we suggest spending two to three days to get a taste of the area.
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Photo Credit: Opening photo by Jakub Koziol; other photos by Salt & Wind Travel
