11 Things to Do in Pienza (2023)

Fall in love with Pienza – the so-called ideal Renaissance town in Tuscany. This romantic hilltop town is magical.

Want to go? Here are the most wonderful things to do in Pienza.

Pienza Tuscany is famous for a lot of things- UNESCO status, its Pecorino di Pienza, its film location for the movies Romeo and Juliet and the Gladiator, and so much more.

History buffs, photographers, foodies and romantics need to add Pienza to their list. Is that you? Stay with me and let’s tour it together.

This post may contain affiliate links. If you click on an affiliate link, at no additional cost to you, I will earn a small commission if you decide to book. Please check out my privacy policy and disclosure for more information.

11 Top Things to Do in Pienza

#1 People watch in Piazza Pio II

Like any piazza in Italy, it’s where you will find locals gathering, catching up on the latest news, (or maybe it’s the town’s gossip), and children playing football (soccer).

What’s missing in this piazza is the opportunity to dine al fresco, for that, you’ll find dining tables and chairs tucked away on tiny side streets.

This is what makes Pienza’s main square a bit different. I for one rather liked it. It seemed quieter and more intimate. The only real noise you heard was the echoing sounds of the pigeons fluttering about and cooing.

On the side of the square, there is an attractive well, known as the ‘well of dogs’. Camera in hand, you’ll be delighted about all the sites you’re about to explore as many of the Pienza things to do are right here on this piazza.

#2 Marvel at Pienza’s Duomo

The Duomo di Pienza sits on the main square and catches your immediate attention.

The Cathedral was built on the remains of the Romanesque church of Santa Maria which is still visible in the crypt. The facade of this 15th-century cathedral is typical of the Renaissance style and is divided into three parts by arched columns. 

On the left wing of the Cathedral, there is an octagonal, cuspidate bell tower that is reminiscent of the ones Pope Pius II saw in Germany and wanted in the redesign of this ideal Renaissance town.

Fun Fact! The Palazzo Comunale, Pienza’s town hall, is a building that sits on the main square too. It was purposely built shorter than the Cathedral’s bell tower to symbolize the superior power of the church. Nonetheless, it is an attractive building with a contrasting red brick bell tower that was added afterwards.

#3 Tour the Palazzo Piccolomini and Borgia

The Palazzo Piccolomini was the summer residence of Pope Pius II. And, the Palazzo Borgia was a gift from Pope Pius II to Cardinal Rodrigo Borgia (the future Pope Alexander VI).

Take a tour and see the rooms on the main level with period furniture and furnishings from the Renaissance period of Piccolomini palace. Both the inner courtyard and hanging garden, known to be the first roof garden of the Renaissance, are beautiful. Movie buffs might be interested to know this was the film location for Shakespeare’s “Romeo and Juliet” in 1968. 

The Palazzo Borgia is now home to the Diocesan museum. The collection includes local textile work as well as religious artifacts.

Is it worth touring both of these palaces? Absolutely, especially because it grants you access to the impressive panoramic views of the Val d’Orcia and Mount Amiata.

Get your skip-the-line entrance ticket and audio guide here.

#4 Wander aimlessly through Pienza’s small streets

Pienza is meant for strolling.

Corso il Rossellino is the street that runs through the historic city center. From start to end, it might take you 5 minutes to walk it. It’s that short! Yet, it will likely take you an hour or so. Be a little curious and wander the delightful narrow cobblestone streets that lead you in different directions. Of all the Pienza things to do this was my favourite!

With the names of Via dell’Amore (or Love Street) and Via del Bacio (or Kiss Street), you can’t help but fall in love with this Renaissance town. Other pretty streets worth seeking out are Via Dogali, Via del Giglio, and Via della Volpe.

#5 Sample some Pecorino di Pienza cheese

No visit to Pienza is complete until you taste the delicious Pecorino cheese this town is so famous for. Pecorino cheese is a sheep’s milk cheese. Common types that you’re likely familiar with are Pecorino Romano or Pecorino Toscano- a strong tangy, salty flavour that melts in your mouth.

Pecorino cheese is prominently displayed in some of the specialty cheese shops in this region.

Two of the best places to sample are La Bottega del Cacio and La Bottega del Naturista.

If you are visiting in early September, don’t miss the popular festival dedicated to pecorino cheese called Palio del Cacio Fuso. Locals come out and cheer players from each town who roll a round of pecorino cheese around a spindle in the center of the square. I visited Pienza in the spring and missed out. It sounds like one of the fun things to do in Pienza to me!

#6 Admire the vistas from a viewpoint

One of the best parts of being in a hilltop town is of course the views. And, Pienza definitely has some of the best landscape views in Tuscany.

Find your way to Passeggiata Panoramica, along the path of the city wall for one of the best viewpoints in Pienza. Another great viewpoint is Porta al Ciglio (near the parking lot).

Gazing upon the awe-inspiring views of the Val d’Orcia is definitely a must-do and without a doubt one of the top things to do in Pienza.

#7 Peruse Pienza’s shops and galleries

The main street of Corso il Rossellino is lined with little shops.

There are an abundant amount of food shops showcasing typical Tuscan products, and yes, cheese. For such a small town, it’s always bustling with activity with locals stopping in to say ciao or picking up their daily products.

Foodies will delight in all of the locally made dried pasta, bottles of oil, vinegar, wine and so much more. Other shops include ceramics, cast iron, and leather goods where the artist works and runs the tiny shop.

Visit the Artemisia Art Gallery to see paintings dedicated to the local landscape of Tuscany.

#8 Take a Cooking Class

Immerse yourself in a private dining experience at a local’s home. Enjoy an exclusive cooking demonstration of authentic recipes passed down from generation to generation.

It includes a 4-course dinner with wine from regional cellars.

This experience receives 5 stars as one of the best things to do in Pienza, click here for more information.

#9 Visit Pienza’s notable churches

Beyond the main Cathedral, Pienza also has four other churches that are worth visiting:

• San Francesco – a Gothic-style 13th-century church
• Cappella della Madonna di Vitaleta or Chapel Vitaleta is a tiny, photogenic 12th-century chapel in the middle of the countryside as you are coming or leaving Pienza

#10 Go to Gladiator Point

Sitting below the city wall is the 11th-century church of Pieve di Corsignano. This church is known as one of the most important Romanesque monuments of the region. It is also where Pope Pius II and his nephew Pope Pius III were baptized.

From here take the 5-minute walk to De Cypresses or Gladiator point. This pathway is from the opening scene of the Gladiator movie and is incredibly beautiful.  

#11 Stay for sunset watching

If you can time it right, visit Pienza to watch the sunset. Locals gather along the bastion wall and nearby restaurants serve the loved Aperol Spritz cocktails. It’s so romantic to watch the sun slowly dip down over the horizon casting a soft light.

Sunset watching – without question is one of the most wonderful things to do in Pienza!

Best Restaurants in Pienza

1. L’Osteria Baccus – a farm-to-table restaurant with a cozy vibe and good food, a great spot for lunch
2. Sperone Nudo – your authentic Tuscan restaurant with bricked walls and ceilings serves authentic cuisine with a modern twist, just like their interior
3. Trattoria La Chiocciola – is a casual family-style restaurant that promises good food at reasonable prices
4. Il Rossellino – this restaurant just might have the prettiest terrace and best views, this restaurant is your best choice for a long lunch or later dinner

Except to find on every menu the pecorino cheese is the star ingredient. The best dish to have is cacio e pepe (cheese and pepper). In Pienza, they serve it with handmade pasta noodles called pici which is a thicker version of spaghetti.

Buon appetito!

History of Pienza Tuscany

So, how did this Italian town come to be?

Enea Silvio Piccolomini elected Pope Pius II in 1458, and it was he who wanted to transform his birthplace, the anonymous village of Corsignano, into the ideal Renaissance town. He hired Bernardo Rossellino, and it only took 4 short years to rebuild and rename the town of Pienza.

Pienza has remained virtually unchanged since the 15th century making it a top reason to come and visit this UNESCO-status town.

Where is Pienza and How to Get There

Pienza is a hilltop town that sits in the region of Val d’Orcia in the province of Siena.

Although this area of southern Tuscany is known for its other notable towns of Siena, Montepulciano, and San Gimignano – Pienza is truly a hidden gem! This town is located right between Montepulciano and Montalcino, making it easy to see all three in one day.

The nearest airport is Florence, and Florence to Pienza is 120 km. Even though there is a bus that runs from Siena to Pienza you’re going to want to rent a car. It’s the only way to visit town to town and that’s exactly why you go to Tuscany. Alternatively, many fly into the Rome International airport and drive to Tuscany which is 188 km.

Parking in Pienza is at the top of the hill, unlike other towns where you have to park and walk up a steep incline.

Where to Stay in Pienza

If you are touring Tuscan towns, Pienza makes a lovely day trip. If rushed, you could combine it with Montepulciano (15 km) and Montalcino (20 km), allowing you to see three small, yet lovely towns in one day. Maybe one for breakfast, one for lunch and one for dinner. Pienza is a destination for its restaurants. I recommend La Terrazza del Choistro or Osteria Sette di Vino.  

But if you would like to make Pienza your home base, this romantic town offers a wide range of accommodations, both in the old town and close to it. From agritourism to apartments to vineyard estates to wineries, agritourism, everything is represented here. Here are some of the best accommodations in Pienza.

• Hotel in a 15th-century convent: Relais II Chiostro di Pienza is located along the panoramic path on the city wall. This luxury hotel offers panoramic views, beautiful gardens, and a pool.
• B&B in the old town: La Bellavita B&B delights with nice rooms and a very nice roof terrace with a fantastic view over the old town of Pienza.
• Hotel in the historic center: Residence San Gregorio is a small, beautiful hotel at the gates of the historical center.
• Casa Rosana: a 2-bedroom (sleeps 6) farmhouse from 1619 for rent. Perched on the hills overlooking the Val d ‘Orcia.
• Agriturismo in a great location: Agriturismo Il Casalino is a 19th-century farmhouse with individual apartments.
• Agriturismo with swimming pool: Agriturismo Marinello is a beautiful farmhouse in a quiet setting overlooking Pienza. 
• Or, explore other properties using Booking.com

Other Towns Near Pienza

Whether you decide to make Pienza your base to explore other nearby towns or are still looking for ideas, consider these other beautiful towns that are 60 km or less from Pienza.

• Monticchiello to Pienza – 10 km
• San Quirico d’Orcia to Pienza 10 km
• Montefollonico to Pienza – 11 km
• Montepulciano to Pienza – 15 km
• Torrita di Siena to Pienza – 17 km
• Montalcino to Pienza – 23 km
• Lucignano to Pienza – 31 km
• Cortona to Pienza – 45 km
• Siena to Pienza – 59 km
• Arezzo to Pienza – 60 km

FAQ

Italy Travel Resources

To help with your Tuscany trip inspiration and planning, check out some of my other articles, as well as other cities in Italy.

Tuscany

• 19 Best Tuscan Towns to visit
• Guide to Florence – top things to do
• Guide to Siena – how to spend one day
• Guide to Cortona – top things to do

Italy

• Venice vs Florence: which city is better?
• Guide to Rome
• 18 Best UNESCO World Heritage Sites in Italy
• Things to you need to know before you go to Italy

If you LOVE EUROPEAN TRAVEL or planning a TRIP TO EUROPE, subscribe to my website! I will share my love of Europe with you, along with travel planning tips and inspiration. And, you’ll get a FREE gift for signing up – 30 Bucketlist Places in Europe! Join, and let’s be travel friends!

As a holidaymaker

Tuscany is definitely one of those destinations that you’re sad to leave and you long to return to. And Pienza, this perfectly preserved 15th-century town is definitely one that leaves a lasting memory.

There are just so many small, quiet towns dotted along the Tuscan hills. Pienza just happens to be one of my favourites. I immediately fell in love with this romantic hilltop town with its incredible views and I know you will too. I hope this list of things to do in Pienza will help you visit this ideal Renaissance town.