A Curated Guide To Pienza Italy

I visited Pienza Italy, during a trip to Tuscany last June with my sister and brother-in-law. While we have been to Tuscany many times before, this was our first time in Val d’Orcia, and we didn’t want to miss this lovely small Tuscan town. We spent an entire day exploring Pienza Tuscany, and its immediate surroundings, so I thought I’d share my best tips for visiting.

Pienza is one of those places in Italy that feels perfectly designed — because, in a way, it was. Built in the 15th century as Pope Pius II’s vision of the “ideal Renaissance city,” Pienza today is a blend of elegant architecture and honey-colored stone.

Whether you come for the architecture, the food (Pienza is famous for its pecorino cheese), or simply to linger on a quiet terrace, Pienza captures the essence of Tuscany: beauty, simplicity, and balance.

In this Pienza guide, I cover the best things to do in Pienza, and I share useful tips that will help you plan your visit.

Are you planning a trip to Tuscany? Don’t forget to read my post, 15 Incredible Places To Visit In Tuscany, for inspiration on what to see in the region.

Quick Overview of Pienza

Short on time? Here’s a quick overview of the best things to do in Pienza, and some tips to plan your visit.

BEST PLACES TO VISIT AND THINGS TO DO IN PIENZA:

• Historic center
• Pienza Cathedral
• Palazzo Piccolomini and its Gardens
• Diocesan Museum at Palazzo Borgia
• City walls
• Cheese tasting

BEST GUIDED DAY TRIPS TO PIENZA:

• Guided tour of Val d’Orcia from Florence
• Guided tour of Val d’Orcia from Rome
• Guided tour of Montepulciano and Pienza from Siena

ESSENTIAL PIENZA TIPS:

• If you want to be more independent, consider renting a car in Florence to explore Pienza and the Val d’Orcia.
• Give yourself enough time to explore Pienza. It’s small, but there’s quite a bit to see, and it’s so pretty that you will want to linger a bit longer.
• Get the All Inclusive Pass Pienza città di Luce, which includes access to Palazzo Piccolomini and its Garden, Palazzo Borgia and the Museo Diocesano, the Duomo, the Crypt and the Labirynt.

Best Time To Visit Pienza Italy

The best time to visit Pienza, Tuscany is either April and May or September and October, when the Val d’Orcia landscape is green, warm, and perfect for exploring on foot.

April and May offer mild temperatures, blooming fields, and clear light for photography. June starts being rather hot already – we visited in mid-June and we certainly suffered the heat.

July and August are the hottest and busiest months, often above 30°C, but full of energy with open-air concerts and village festivals. If you are traveling to Italy in the summer, visit earlier in the morning or later in the afternoon. The central hours can be very hot, and there will be more crowds around.

For many travelers, September and October are ideal: the weather cools slightly, vineyards turn golden, and local harvest events fill the calendar.

Winter (November to March) is peaceful and atmospheric: the days are shorter, the tourist crowds gone. I visited San Gimignano in the winter and if it’s anything like that, it means that you’ll have the town to yourself, and a really cozy and local atmosphere.

If you want pleasant weather, open views, and fewer tourists, the best months to visit Pienza are April and May or September and October — the perfect balance between scenery, comfort, and crowd levels.

Planning a trip to Italy? My post, The Best Time To Visit Italy, will help you decide on your travel dates.

How To Get To Pienza, Italy

To be fair, Pienza isn’t exactly well-connected to the rest of Tuscany: there’s no highway nearby, and no train station either. Don’t worry, though, I will explain how to get there and you’ll see it’s almost a breeze.

I have a post on How To Get Around Italy that will help you decide on what mode of transportation to use for your Italy trip.

By car

The easiest and most scenic way to get to Pienza is by car. It will take you about 2 hours to get there by car from Florence, just over one hour to drive there from Siena, and 2.5 hours to get there from Rome (I still think it’s a bit too long of a drive to consider this as a day trip from Rome).

When I visited, I drove from Montepulciano – it took me about 20 minutes.

The beauty of driving in this region of Italy is that you will have the freedom to go at your own pace, and stop along the way at beautiful vineyards, viewpoints (there are many), and hilltop towns like San Quirico d’Orcia, Montalcino or even Montepulciano (in case you are coming from Florence.

The route is easy to follow and incredibly beautiful. The last stretch of the drive you’ll go along hills with golden wheat fields and the cypress trees that are so typical of the Val d’Orcia.

You shouldn’t have trouble parking in Pienza. We did not, and we visited in the peak season. There are several lots available just outside the historic centre, which is pedestrian-only.

I recommend Discover Cars as the best comparison site for car rental. It’s what I use wherever I travel, and of course I also used it for this Tuscany trip.

For guidance on car rental, head over to my post, The Best Tips For Renting A Car In Italy. It will help you decide on the kind of car and the insurance to get. I also have a post on How To Master Toll Roads In Italy that you need to read.

By guided tour

If you don’t want to rent a car, the easiest way to get to Pienza from Florence or Rome is by guided tour. In this case, you’ll have plenty of options to pick from. Here are some top picks:

This guided tour of Val d’Orcia includes transportation from Florence and lunch with wine tasting. It stops in Pienza, Montepulciano and the Abbey of Sant’Antimo.

There’s also this guided tour from Rome which is quite similar to the one departing from Florence.

In case you are departing from Siena, there’s this small group tour which stops in both Pienza and Montepulciano, and includes lunch with wine tasting at a local farm.

By public transport

There’s no train station in Pienza, which makes getting there by public transport a bit of an ordeal if you are coming from Florence or Rome.

The easiest route if you want to travel by train is to take the train to Chiusi – Chianciano Terme, which takes about 1 hour and 45 minutes, and then take a taxi from there (another 45 minutes).

If you are traveling from Montepulciano, it’s much easier: take the 112 bus headed to Buonconvento. You need to get off after 17 stops, and it only takes about 20 minutes.

By bike

If you are romantic, have plenty of time, and are seriously fit, you could consider cycling to Pienza, Tuscany.

Pienza is located along the scenic Strade Bianche, a network of unpaved white roads that twist through the Val d’Orcia and have become iconic among cyclists in Italy. These gravel routes offer rolling hills, sweeping views, and almost no traffic.

Let me stress once again that you need to be fit to do this, not to mention an expert cyclist: there are long climbs and the terrain is constantly changing. Having said that, reaching Pienza by bike is incredibly rewarding.

Best Things To Do In Pienza, Italy

Explore the historic center

Let me start with one of the best things to do in Pienza, Italy – the one thing we did as soon as we arrived. Simply wander. Don’t worry, it’s impossible to get lost. The historic center develops along a main street, Corso il Rossellino, which runs from the Porta al Prato on the west side to the Porta al Ciglio on the east.

It’s a charming place. Picture elegant palaces, small and inviting trattorias, and artisan shops selling pecorino cheese and ceramics.

At the heart of town is Piazza Pio II, Pienza’s main square and one of the most beautiful examples of Renaissance urban design in Italy. It’s framed by Palazzo Piccolomini, the Cathedral, and the town hall. It’s the perfect meeting point for locals and tourists alike.

Useful tip: The narrow alleys just of the Corso il Rossellino are truly charming. If you walk past the left side of the Cathedral, you’ll get to Via del Casello, a fantastic panoramic spot, and from there you can reach Via dell’Amore and Via del Bacio.

Visit Pienza Cathedral

You will find the Pienza Cathedral, or Duomo di Santa Maria Assunta, in Piazza Pio II at the heart of town. The church was commissioned in the 15th century by Pope Pius II, as part of his grand vision to turn his birthplace into the perfect Renaissance city.

It’s a beautiful, spacious church with tall windows that allow lots of natural light. Inside, you’ll be able to admire works of the Sienese school from the 15th century.

Make sure to also visit the crypt beneath the church. There are traces of medieval stonework and relics from earlier structures.

Explore Palazzo Piccolomini and its Gardens

You simply can’t skip Palazzo Piccolomini when you are in Pienza. This was the summer residence of Pope Pius II, designed by Bernardo Rossellino. It is also one of the earliest examples of Renaissance domestic architecture in Italy.

The palace was designed with precision and proportion in mind — every window, arch, and courtyard detail aligns with that humanist idea of order and balance that defines Pienza.

You can visit Palazzo Piccolomini only on guided tours that take you through the furnished rooms and to the loggia from where you can get a stunning view of the Val d’Orcia. Taking photos is now allowed inside the palace.

Below the Palace, there are the palace gardens, which unfold in perfect symmetry — a geometric design of trimmed box hedges, roses, and terraces overlooking the Val d’Orcia. Unfortunately, when we visited Pienza, the Gardens were closed for an event and we were only able to catch a glimpe from the Loggia.

Visit the Diocesan Museum at Palazzo Borgia

Located in Corso il Rossellino, a 1-minute walk from the Cathedral, you will find Palazzo Borgia, home to the Diocesan Museum of Pienza. The building was originally given by Pope Pius II to Cardinal Rodrigo Borgia — the future Pope Alexander VI — and now houses an impressive collection of sacred art from churches across the Val d’Orcia.

Inside there are rooms filled with 14th- and 15th-century paintings, wooden sculptures, illuminated manuscripts, and finely embroidered vestments. My favorite pieces there were the works by Vecchietta, Lorenzo di Pietro, and other Sienese masters.

Even if religious art isn’t your main draw (it isn’t for me), it’s worth stepping inside for a sense of how deeply the Renaissance ideals of Pienza were rooted in both faith and artistry. It doesn’t take long to visit.

Take a stroll along the city walls

One of top things to do in Pienza is to walk along its panoramic city walls. Running along the southern edge of town, don’t expect these to be defensive ramparts like in Siena. It’s more like a promenade from which you can enjoy breathtaking views.

You can get uninterrupted views across the Val d’Orcia: its characteristic rolling hills, winding roads, tidy farms, and those unmistakable rows of cypress trees that make this part of Tuscany so famous.

Tip: Enjoy this walk in the early morning or late afternoon hours for the best light.

Go cheese tasting in Pienza

Cheese tasting is what to do in Pienza for foodies. Here, you’ll want to try the famous pecorino di Pienza, the local sheep’s milk cheese that’s been made here for centuries.

You’ll find versions of pecorino that are fresh and soft (pecorino fresco), firm and crumbly (stagionato), or aged. Most cheese shops in Pienza offer tastings, and the owners are usually happy to explain the differences or suggest pairings with honey or local wine.

Here are some places where you can taste the pecorino di Pienza:

• Marusco e Maria – A classic family-run deli offering tastings paired with local wine and honey.
• Taverna del Pecorino – Another no-frills deli located in the historic center of Pienza.
• Caseificio Cugusi – Between Pienza and Montepulciano, it is known for its award-winning pecorino and the scenic picnic area overlooking the vineyards. To us, it was interesting to notice how the lastname Cugusi is typical Sardinian (and we make excellent pecorino cheese in Sardinia).

For a deeper experience, consider this dairy farm tour with cheese tasting experience in Pienza. You’ll discover the most traditional cheeses in Tuscany.

Visit the surrounding Val d’Orcia

There are many places that you can easily visit close to Pienza.

Here are some that I recommend, and that are all within easy driving distance:

• Montepulciano – Known for its Vino Nobile and the Renaissance Palaces, it’s a lovely hilltop town with a quaint atmosphere.
• Montalcino – This gorgeous town is famous for its Brunello di Montalcino wine. There’s a fortress where you can get sweeping views of the town and its surroundings. It’s one of the most touristy places in the Val d’Orcia.
• San Quirico d’Orcia – Significantly lesser-known compared to Pienza and Montalcino, yet lovely. There are some gorgeous gardens to explore, and a few good restaurants.
• Bagno Vignoni – Home to the gorgeous Piazza delle Sorgenti, a huge pool of natural thermal water where bathing is no longer possible. Just outside the village, there are free thermal baths easy to reach on foot.

I also have a post on the Best Things To Do In Val d’Orcia that you should read. You should also read my Guide To Montepulciano.

Where to stay in Pienza

While you can easily visit Pienza on day trips from Florence and even Rome, you may want to spend a few nights there and use it as a base to explore the rest of Val d’Orcia. If you decide to do that, you won’t have trouble finding good accommodation options.

Here are my recommended places to stay in Pienza:

• Agriturismo il Casalino – Perfect if you have a car, it has cozy rooms facing a beautiful garden, and a nice pool to relax.
• La Sesta Luna – Nice small apartment in the historic center of Pienza, complete with a kitchen and everything you need for a comfortable stay.
• Palazzo Massaini Le Scuderie – Gorgeous suites in a beautifully refurbished historic building just outside Pienza. There’s a nice outdoor pool and family rooms are available too.

Best Places to Eat in Pienza

While it is faily small, there are some excellent restaurants in Pienza. Here are the ones you should try:

• Il Poderuccio – A family-run restaurant that serves traditional Tuscan food and products. The atmosphere is very easy-going.
• Sette Di Vino – The most popular restaurant in Pienza, for all the good reasons. Food is delicious, service spot on, and prices fair.
• La Posta – Local café in the piazza by the Cathedral, it’s a favorite meeting point and the best place for a coffee and a quick bite.
• Trattoria Fiorella – Another easygoing place serving typical Tuscan fare.

Tip: Book your table in advance. This is especially necessary in the summer months, when lots of people visit Pienza.

FAQs About Pienza

Further Readings

These other posts will help you plan your trip to Tuscany:

• Best Florence Travel Tips
• What To See And Do In Florence