If you’re planning a road trip through Tuscany, there’s one magical town that you simply cannot skip—Pienza. Nestled in the rolling hills of the Val d’Orcia, Pienza is a postcard-perfect town that feels like stepping into an Italian Renaissance painting. It’s not just a place to visit; it’s an experience to savor, with a rich history, charming streets, mouth-watering food, and unforgettable views.
On my recent road trip, I visited Pienza, along with Val d’Orcia, Montepulciano, Cortona, Arezzo, San Gimignano, and Siena. (I revisited San Gimignano and Siena. I could never get enough of the beauty of these towns!).
In this Pienza travel guide, I’ll take you through everything you need to know about Pienza, from its history to the best things to do, where to eat, and what makes this town an absolute must-see on your Tuscan road trip.
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A Brief History of Pienza: From a Humble Village to the “Ideal” Town
Pienza is a place with a fascinating history, all tied to one man: Pope Pius II. Originally a small, medieval village called Corsignano, it was transformed into a Renaissance utopia by Pope Pius II (born Enea Silvio Piccolomini). In the 15th century, he commissioned architect Bernardo Rossellino to redesign his birth town into what we see today—a model of Renaissance urban planning.
The town was renamed Pienza (meaning the City of Pius) in honor of the pope, who envisioned it as an “ideal city” that combined beauty, function, and harmony. It was one of the first towns in Italy to be designed with such precision and foresight. Its stunning architecture is a reflection of that vision. Pienza is a World Heritage Site today.
Pienza Travel Guide: Things To Do in Pienza For A Day Well Spent
Pienza is a small town, but every corner of it is filled with charm. Whether you’re wandering through its narrow streets, soaking in the views, or enjoying local delicacies, there’s plenty to keep you occupied for a few hours.
1. Stroll Through Corso il Rosellino
The main street of Pienza, Corso il Rosellino, is the perfect place to begin your exploration. Lined with picturesque buildings, boutiques, and cafes, it’s a lovely place to walk, take in the sights, and feel the town’s rhythm. The street leads you from the Porta al Prato on the one side of Pienza across the town’s central square, Piazza Pio II, to Porta al Ciglio on the other side of the town.
2. Admire Piazza Pio II: The Heart of Pienza
This stunning square is the centerpiece of the town. It’s flanked by some of Pienza’s most important landmarks, including the beautiful Pienza Cathedral (Cattedrale di Santa Maria Assunta), the Palazzo Piccolomini, and the Palazzo Borgia. The square is the perfect place to sit and soak in the atmosphere, enjoying a coffee while gazing at the elegant architecture.
3. Explore Pienza’s Stunning Palaces
- Palazzo Piccolomini: A Renaissance masterpiece, this palace was once the home of Pope Pius II’s family. It was rebuilt in the mid-15th century as the summer residence of Pope Pius II. The palace is an architectural gem, with an elegant courtyard and views over the Val d’Orcia valley that will take your breath away.
Many movies, including Medici (TV Series), have been filmed in Palazzo Piccolomini in Pienza. The Palace is next to the Cathedral on the main square, in the heart of Pienza. It is a must-vist in Pienza!
Pienza City of Light Pass (14 €, valid for 2 days) gives access to the Piccolomini Palace, Borgia Palace, and the Cathedral’s Crypt. Taking photos inside the place is not allowed. - Palazzo Borgia: Another gorgeous palace, Palazzo Borgia is now home to the town’s museum. It’s a wonderful spot to dive deeper into Pienza’s history and art. The museum has 11 rooms and holds an art collection of the Sienese school of the 15th century, Sienese figurative art of the 14 century, and goldsmith objects dating from the 13th to the 19th century.
4. Visit the Churches of Pienza
Pienza has some impressive churches that add to its charm:
- Pienza Cathedral (Cattedrale di Santa Maria Assunta): Located right in the heart of Piazza Pio II, this cathedral is a blend of Gothic and Renaissance styles. Step inside to admire its elegant interior. On my visit to Pienza, I stumbled upon a wedding in the cathedral. When you see the Cathedral and Pienza it gets perfectly clear to understand why it is one of the best places to get married in Tuscany.
Visiting the Cathedral is free. But, there is a small fee for visiting the crypt below the Cathedral. Pienza City Pass (14 €, valid for 2 days) includes a visit to it. - Chiesa di San Francesco: Situated a few steps from the Cathedral, this church is dedicated to St. Francis and has a more simple, rustic feel than some of the other churches in town. Its exterior is incomplete, but the interior has remains of the 14th-century frescoes. Its quiet beauty makes it a peaceful spot for reflection.
- Pieve dei Santi Vito e Modesto: Located just outside the town, this lovely Romanesque church from the 12th century offers a step back in time and provides a serene contrast to the grandeur of the city’s other sites. This church is less than 1 km from the historic center of Pienza.
5. Wander the Prettiest Streets
Pienza is known for its charming narrow streets, many of which are a photographer’s dream. Don’t miss:
- Via del Baccio: A lovely, quieter street that’s perfect for a relaxed stroll.
- Via dell’Amore: As the name suggests, this is a romantic lane, perfect for couples.
- Via della Fortuna: Another enchanting street that offers a glimpse into the everyday life of the town’s residents.
6. Enjoy the City Walls
Pienza is surrounded by beautiful city walls that date back to the Renaissance period. Take a walk along the walls and be rewarded with spectacular views of the Val d’Orcia landscape, one of Tuscany’s most beautiful areas.
7. Shop for Local Goods
Pienza isn’t just a place to explore—it’s also a place to shop for unique, handmade Tuscan goods. From leather bags and artisan ceramics to locally made olive oils and truffle products, there’s something here for every taste. You can pick up a bottle of local extra virgin olive oil or a beautiful handcrafted leather wallet as a souvenir to remind you of your Tuscan adventure.
8. Indulge in Pienza’s Culinary Delights
When you’re in Pienza, eating is not just a necessity—it’s an experience. The town is known for its pecorino cheese, and no visit would be complete without tasting some. Pecorino di Pienza is the star of Pienza’s food scene. You can find the famous sheep’s milk cheese in every form—young, aged, truffle-infused, and more. Stop by a local cheese shop and treat yourself to a sample. You might even end up taking a wheel home (trust me, you’ll want to!).
For a meal, head to Ristorante Il Rossellino for a delicious Tuscan feast. Don’t miss the pasta alla pappardelle (wide ribbon-like noodles with wild boar sauce) and a hearty steak—bistecca alla Fiorentina, anyone?
9. Relax and Take in the Views
Pienza’s beauty is not just in its buildings but in its location. The town sits atop a hill, offering sweeping views of the rolling Tuscan countryside. Spend some time simply enjoying the scenery, whether you’re sitting in a café or wandering the streets.
10. Skip going to the Gladiator Viewpoint
The Gladiator Viewpoint offers stunning views of the gorgeous Val d’Orcia. The viewpoint appeared on the screens in the famous opening scene of the Gladiator movie. It instantly became one of the most photographed places in Tuscany, attracting crowds.
The Vista Point is on private property and is no longer available for public access. I drove there but had no luck. I wasn’t able to access the property. However, there are plenty of fabulous viewpoints in Val d’Orcia that will make you stop driving.
How Much Time to Spend in Pienza
Pienza is a small town, so you can easily explore it in 2-3 hours. If you want to take your time, enjoy a leisurely lunch, and savor the views, half of a day is ideal. But if you’re on a tight schedule, 2 -3 hours will still give you a good sense of the town’s beauty and charm.
Is Pienza Worth Visiting?
Absolutely! If you’re road-tripping through Tuscany, Pienza is a must-see. It’s an easy stop that packs a big punch in terms of history, beauty, and food. The town’s UNESCO World Heritage status speaks to its cultural importance, and its beauty is undeniable. Whether you’re into history, art, food, or simply stunning landscapes, you will love Pienza!
Where is Pienza
Pienza is located in the southern part of Tuscany, about 40 minutes from Siena and an hour and a half from Florence. It’s also just a short drive from other iconic Tuscan towns like Montalcino (25 minutes away) and Montepulciano (15 minutes away).
How to Get to Pienza
To get to Pienza, you’ll most likely need a car, as it’s located in the countryside and public transportation options are limited. If you’re driving, the roads are scenic, and getting there is half the fun!
The nearest airport to Pienza is Perugia (PEG) Airport which is 66.7 km away. Other nearby airports include Florence (FLR) (89.4 km away), Pisa (PSA) (124.5 km away), and Rome (FCO) (150.1 km away.)
I flew into Pisa, picked up my rental car at the airport, which I booked online in advance, and embarked on my trip. Check out rental cars here and find out how affordable they can be when booking in advance. The most expensive rental cars are when hiring at airports!
To get to Pienza, you’ll most likely need a car, as it’s located in the countryside and public transportation options are limited. If you’re driving, the roads are scenic, and getting there is half the fun!
The nearest airport to Pienza is Perugia (PEG) Airport which is 66.7 km away. Other nearby airports include Florence (FLR) (89.4 km away), Pisa (PSA) (124.5 km away), and Rome (FCO) (150.1 km away.)
I flew into Pisa, picked up my rental car at the airport, which I booked online in advance, and embarked on my trip. Check out rental cars here and find out how affordable they can be when booking in advance. The most expensive rental cars are when hiring at airports!
You can visit also Pienza on a day tour from Siena, or on a day tour from Florence.
When to Visit Pienza
As for when to visit, spring and fall are the best times. The weather is pleasant, and the crowds are fewer than in summer. Plus, the surrounding countryside is stunning in these seasons, with the rolling hills dotted with vineyards, olive groves, and cypress trees. I visited Pienza in May when the rolling Tuscan hills got surreal green! I can’t recommend enough visiting Tuscany in May!
What to Do Nearby Pienza
If you have extra time, the Val d’Orcia region is full of beautiful places to explore:
- Montalcino (25 km): Famous for its Brunello wine and medieval fortress.
- Montepulciano (15 km): A hilltop town known for its wine and Renaissance architecture.
- Bagno Vignoni (15 km): A unique village with a thermal water pool right in the middle of the town.
- Cappella di Vitaleta (7 km): One of Tuscany’s most photographed spots, this picturesque chapel is surrounded by cypress trees and offers an iconic Tuscan view.
Final Thoughts: Why You Should Visit Pienza
Pienza is the epitome of Tuscany—charming, historic, and full of life. Whether you’re wandering its cobblestone streets, savoring local cheeses, sampling delicious Tuscan food, or gazing at the countryside views, every moment here feels like a little slice of paradise. So, if you’re looking for a place to immerse yourself in the essence of Tuscany, make sure Pienza is on your itinerary. You won’t regret it!
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