I live in Italy, which means places like Pienza in Tuscany are just a short drive away. I spent a long weekend there exploring every corner of the old town and the surrounding Val d'Orcia countryside - and I left already wanting to return. Here's everything I'd tell you before you go!

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I’ll be honest, I knew absolutely nothing about Pienza before serendipitously finding accommodation just a short drive from the old town while visiting Tuscany. We had planned to visit the nearby town of Montepulciano, and stumbled upon this tiny but impossibly charming town mostly by accident. A very, very happy accident.

Pienza is one of those small Italian towns that makes you stop every 5 minutes and just look around in awe. Every time we turned a corner - at the piazza, at the city walls, at the Gladiator field, even at our chosen aperitivo spot (more on that below) - I kept having the exact same reaction: how is this real?!

Pienza is a small Renaissance hill town in the heart of Val d'Orcia, famous for its pecorino cheese (which is super delicious, by the way), its UNESCO-listed architecture, and its views over one of the most photographed landscapes in all of Tuscany.

It's also small enough to cover in a single day - which makes it one of the best day trips in Tuscany, whether you're based in Florence, Siena, or anywhere in between. Although I would actually recommend staying here locally, if you have the opportunity. Regardless, I’m sharing the very best things to do in Pienza, and some essential tips for visiting. Let’s go - or rather, andiamo!

Table of Contents

Introduction
A Quick History of Pienza
Where is Pienza in Tuscany?
How to Get to Pienza
My Experience in Pienza
Best Things to Do in Pienza
Other Things to Do Near Pienza
Where to Stay
Where to Eat and Drink
FAQ
Final Thoughts

Short on time? Here are my top hotel picks in Pienza, Italy:

La Bandita Townhouse ⭐⭐⭐
Relais il Chiostro di Pienza ⭐⭐⭐⭐
Agriturismo Il Casalino ⭐⭐⭐⭐
Mascagni Farmhouse (private rental)

A Quick History of Pienza

Pienza, known as the "Ideal City," owes all of its character to Pope Pius II. Originally a small village called Corsignano, the Pope hired architect Bernardo Rossellino in the 15th century to redesign his hometown into a Renaissance masterpiece - a harmonious, humanist city that reflected the ideals of that age.

The result was Piazza Pio II and the surrounding buildings, so perfectly proportioned and preserved that the town earned UNESCO World Heritage status. Walking through it today, it still feels like the Renaissance ended about twenty minutes ago.

Where is Pienza in Tuscany?

Pienza sits right in the heart of Val d'Orcia - the UNESCO-listed valley of rolling hills, cypress-lined roads, and hilltop medieval towns that you've seen on every Tuscan postcard. It's perfectly situated for exploring the surrounding area: Montepulciano is less than 20 minutes away, Montalcino is just under 30 minutes, and Florence is about 1.5 hours by car.

Map of Pienza, Italy

Use this map to plan your trip to Pienza! The locations are organized by type. Blue pins are the “best things to do” locations, green pins are things to see and do nearby, purple pins are accommodations, and red pins are places to eat. Zoom in on Pienza’s historic town center to reveal the majority of the saved pins.

How to Get to Pienza

By Car

Driving is the most practical way to reach Pienza - the approach through Val d'Orcia is as beautiful as the destination itself. From Florence, allow 1.5 hours via Siena. From Rome, plan for about 2.5 hours.

>> Find the best car rental rates with AutoEurope

Where to Park in Pienza

Pienza has various paid parking lots just outside the historic center, all accepting credit cards. During peak season (April through October) arrive early on weekends - they fill up faster than you'd expect.

Parcheggio Via del Cassello - right beneath the town walls, with a short beautiful walk up to the main square. My recommendation for first-timers.
Parcheggio Pienza - slightly larger, also very convenient
Parcheggio via Degli Archi - the newest and largest option, a few minutes' walk from the center

By Guided Tour

If you'd rather not drive, day trips from Florence and Siena are widely available and often combine Pienza with other Val d'Orcia highlights like Montepulciano and Montalcino - usually with wine tastings included.

>> From Siena: Pienza and Montepulciano Small-Group Tour

>> From Florence: Val D'Orcia Tour with Wine Tasting

My Experience in Pienza

I visited Pienza on a long weekend and spent time exploring the town itself as well as the surrounding Val d'Orcia countryside - the Gladiator field, a gorgeous olive oil tasting at a nearby farm, and a sunset aperitivo that I cannot stop thinking about. I stayed at an agriturismo in the hills outside of town, which meant waking up to those famous rolling views every morning. More on that in the Where to Stay section.

I've only been once so far, and returning is essentially a non-negotiable for me. There are few places in Italy that made me feel so immediately and completely enchanted as Pienza did.

Best Things to Do in Pienza

1. Stroll Through Piazza Pio II, Pienza's Main Square

Piazza Pio II is the heart of Pienza and the first place that we walked into after entering the city walls. The square's proportions create a subtle optical illusion that makes everything look even grander than it already is - the Duomo anchoring one end, the Palazzo Piccolomini and Palazzo Borgia on both sides, and 500 years of Renaissance architecture looking like it was built just last week.

Early morning is the best time to be here, before the day-trippers arrive and the square fills up. Grab a coffee (or gelato!) from a nearby café, find a spot to sit, and just take it in.

2. Visit the Palazzo Piccolomini and Its Gardens

The Palazzo Piccolomini, once home to Pope Pius II, offers guided tours through its Renaissance interiors - but the real draw is the hanging garden at the back, which supposedly has some of the most extraordinary views in all of Val d'Orcia.

I say “supposedly” because I missed the opening time by about 15 minutes on my visit, which I'm still quite disappointed about. It's at the top of my list for the return trip. Opening hours are typically Monday to Sunday 10:00am - 4:30pm (closed Tuesdays), with a €7 entrance fee for adults. Always check the official website before visiting as hours shift seasonally.

3. Walk the City Walls for Panoramic Views

For sweeping views of Val d'Orcia without spending anything, walk along the edge of town on top of the medieval walls. Via Gozzante was my personal favorite stretch - the views along here are extraordinary and somehow barely crowded. You can also walk down the romantically named Via dell'Amore (Street of Love) to an observation deck with a wide panorama over the rolling hills and cypress trees below.

The light changes dramatically throughout the day, so if you can, it's worth passing through at both morning and late afternoon.

4. Taste Pienza’s Famous Pecorino Cheese

Pienza is famous across Italy for its pecorino cheese, or "Pecorino di Pienza," made from sheep’s milk and aged to perfection in oak barrels. Historically, this delicious cheese was aged in local caves. Yes, caves!

The shops along the Corso il Rossellino are stocked with varieties ranging from fresh and mild to deeply aged, plus unusual flavors that you won't find anywhere else. I made a not-so-quick stop at Marusco e Maria, a shop in the heart of town where you can peruse all sorts of different types before buying. We opted for a blueberry-filled pecorino on our last trip, and now I'm dying to buy some others!

5. Enjoy Aperitivo with a View at Idyllium

This was one of the highlights of the entire trip and the experience I keep recommending to everyone. Idyllium is a cocktail bar and restaurant perched on the edge of Pienza with a terrace that looks directly out over Val d'Orcia. We arrived at golden hour, ordered some spritzes on the specials menu (cannot for the life of me remember the name) and a charcuterie plate that came loaded with some of the most delicious cheeses and cured meats I've had in all of Italy, and just sat there watching the sun move across the valley.

The view from that terrace looks like a movie set. I mean that in the most literal way - the disbelief and pure magic of looking out at those rolling hills in that light is something I didn't fully expect, and a photo won’t quite do justice. Book a reservation in advance if you're planning to visit for a full meal. We went here simply for aperitivo hour, but this spot fills up, as you can imagine.

6. Visit the Iconic Gladiator Field

Just outside of Pienza sits one of the most photographed spots in Tuscany - the cypress-lined driveway, wheat fields, and stone farmhouse featured in the film Gladiator, widely known as the "Elysian Fields." Perfectly aligned cypress trees leading to a rustic farmhouse against a backdrop of rolling hills. It's iconic and totally surreal to see in person.

We drove down the road from town to a parking spot that got us a bit closer, then walked the rest of the way down. A word of advice from personal experience: wear sneakers, not Birkenstocks (speaking from experience). The walk is easy but the terrain is uneven and mostly dirt, so I definitely regretted my footwear choice.

The field itself is private property. The best viewpoint is located here. Nearest parking options are along the main road (limited) or at the neighboring church's lot. Alternatively, it's actually easier to simply walk down from town, which is roughly a 25-30 minute walk to the panoramic viewpoint.

7. Wander the Streets and Shops

One of the best things to do in Pienza requires no planning at all - just walk! The Corso il Rossellino, the pedestrian-only main street running through the old town, is lined with artisan shops, cascading flowers, and absolutely gorgeous architecture. Keep an eye out for the hidden courtyards tucked off the main street and shops selling locally made goods - these are usually where the best finds are.

Other Things to Do Near Pienza

Olive Oil Tasting at Mascagni Organic Farm

About 20 minutes from Pienza in the rolling hills, Mascagni Organic Farm offers tours and tastings at their extra virgin olive oil farm. Bianca, the owner, is so passionate about her craft and the tasting is one of the most enjoyable food experiences I've had in Italy - you leave understanding and fully appreciating EVOO (extra virgin olive oil).

The experience also includes a full sit-down local food sampling, which means you're not just tasting oil, you're eating a homemade meal straight from their farm. I cannot recommend this highly enough!

>> Book the olive oil tasting

PS. They also have a charming rental on their farm property, which we stayed at and truly never wanted to leave. Check availability on VRBO.

Photography Around Val d'Orcia

The countryside around Pienza is a photographer's dream, and there are plenty of specific spots that I would suggest carving out time to visit. Just 15 minutes away is the Cappella della Madonna di Vitaleta - a 16th century chapel surrounded by cypress trees that is probably one of the most photographed small buildings in Tuscany (don’t quote me on that, but you will see it in heaps of photos!)

Along the roads toward San Quirico d'Orcia and Montepulciano, pull over where possible for those quintessential rolling hill shots. One of my personal favorites is the cypress-lined driveway at Palazzo Massaini, about 5 minutes from the center of Pienza.

The Free Thermal Pools at Bagno Vignoni

Bagno Vignoni is a medieval village built around an ancient Roman thermal pool - the pool itself is the main piazza, which is off-limits for swimming but lovely to look at. However, just around the corner is the Parco dei Mulini, where you can access completely free outdoor thermal pools with that distinctive milky-blue water. A perfect way to end a long day of exploring, as long as that day of exploring wasn’t already in wildly hot summer temperatures! Then, a visit to a cold body of water might be a better choice.

Explore the Nearby Towns

Montepulciano (20 minutes) is a must, and honestly the comparison with Pienza is a tough one. Pienza has a smaller, more intimate feel - but Montepulciano has more to see and do, and some of the best wine and food spots in the region. Both are very much worth your time if you have it.

San Quirico d'Orcia (15 minutes) is another lovely stop - beautiful gardens, a quieter vibe, and a good alternative if you want to avoid peak season crowds.

Montalcino (30 minutes) is the destination for Brunello di Montalcino wine lovers, with numerous tasting rooms and a medieval fortress that you can visit.

Where to Stay in Pienza and Nearby

Staying in Pienza itself - or in the countryside just outside - means experiencing the town after the day-trippers have gone, which is a completely different and better atmosphere.

La Bandita Townhouse - A chic boutique hotel in Pienza mixing Tuscan charm with modern touches, free bikes, lovely garden, and a terrace.

Relais il Chiostro di Pienza - A 15th-century convent turned hotel right in the heart of town with lush gardens and panoramic views.

Agriturismo Il Casalino - A 19th-century farmhouse less than 2km from the center, with Val d'Orcia views and home-cooked meals.

Mascagni Farmhouse - My top recommendation. This is where we stayed, and it was nothing short of magical. A restored 16th-century farmhouse in the countryside with breathtaking sunsets, all necessary modern comforts (the espresso machine was very much appreciated, as was the air conditioning), and that quintessential agriturismo experience of waking up to rolling hills outside your window. Bonus: it’s dog-friendly, too!

Where to Eat and Drink

Beyond Idyllium (which we’ve already talked about!), Pienza has a great selection of restaurants focused on local ingredients and traditional Tuscan cooking.

Look for pici pasta (thick hand-rolled spaghetti native to this area), wild boar, and anything featuring the town's pecorino cheese. Many restaurants have outdoor seating with valley views, which I will always recommend seeking out.

Trattoria Latte di Luna - A charming spot in the old town, open for lunch only, with a cozy and authentic vibe.

Sette di Vino - Classic osteria serving homestyle Italian cuisine with outdoor seating in a lovely square.

La Buca delle Fate - In the heart of the old town, traditional Tuscan menu.

Buon Gusto Gelateria - For gelato. Always get the gelato!

FAQ

Q: Is Pienza worth visiting?

A: Yes - and I'd say that as someone who has now been to a lot of Tuscany's famous hilltop towns. Pienza has an undeniable magic to it that comes from its small size and the fact that it was specifically designed as a “perfect city.” You feel that intentionality and charm when you walk through it. Without a doubt, Pienza should be on your Tuscany itinerary.

Q: Can I visit Pienza as a day trip?

A: Definitely - Pienza is perfect for a day trip. The historic center is compact enough that you can dive into all of the main sights in just a couple of hours, with time left over for shopping, lunch, cheese tasting (an essential, of course) and a stroll along the walls. That said, staying overnight - especially at one of the agriturismos outside of town - turns it into a completely different and slower travel experience.

Q: How far is Pienza from Florence?

A: About 1.5 hours by car, depending on your route. Via Siena is the most scenic option and only adds a few minutes. From Siena itself it's about 50 minutes.

Q: What is Pienza most famous for?

A: Three things: its pecorino cheese (Pecorino di Pienza is considered among the finest in Italy), its Renaissance architecture and UNESCO-listed Piazza Pio II, and its position at the heart of Val d'Orcia - one of the most photogenic landscapes in the world. The Gladiator film location nearby has also brought major attention in recent years.

Q: Pienza or Montepulciano - which should I visit?

A: Both if you can - they're only 20 minutes apart and complement each other well. If I had to pick one: Pienza for a quieter, more intimate experience with some of the best views in Val d'Orcia. Montepulciano if you want more to see and do, particularly for wine lovers. Personally I prefer the smaller atmosphere of Pienza (I love a properly tiny town), but Montepulciano is impossibly charming too. Essentially, I highly recommend fitting both into your schedule.

Q: What is the best time of year to visit Pienza?

A: Spring (April to June) and fall (September to October) are the sweet spots - milder weather, manageable crowds, and the Val d'Orcia landscape at its most beautiful. Summer is very hot and very busy, particularly in July and August. If those are your only options, early morning visits and staying overnight will make a real difference to the experience.

Q: Are there any outdoor activities near Pienza?

A: The Val d'Orcia region is amazing for walking, cycling, and landscape photography - the roads and paths between the hilltop towns are as beautiful as the towns themselves. Cycling through the cypress-lined roads toward Montepulciano or San Quirico d'Orcia is honestly a dream way to spend a morning. E-bike tours are available to make your ride planning a bit simpler, as well as make the ride itself more leisurely (yes, please).

>> Book a guided e-bike tour through Val d'Orcia

Final Thoughts

I’ve said it before but I’ll say it again, every single time we turned a corner in Pienza - at the piazza, at the walls, at the Gladiator field, looking out over the valley - I had the same reaction. How is this real?!

There's something about Pienza that feels like you’ve walked into a movie set. Some travel guides will say that it’s small and barely worth a half-day visit - I could not possibly disagree with that more! In fact, I’d argue that spending at least an overnight in the area is the best way to see Pienza, because you’ll get to immerse yourself in the town like a local for that period of time. Obviously if you’re short on time, a one day visit is perfect. So if you're planning any time in Tuscany, make sure Pienza is on the list.

Buon viaggio!
Have a nice trip!

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How to Spend 24 Hours in Venice, Italy
10 Best Non-Touristy Things to Do in Venice, Italy
How to Get a Gondola Ride in Venice
How to Get to Venice from Marco Polo Airport

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