The Ultimate Guide to Pienza, Italy

Having lived in Italy for the past few years, I’ve learned that some places don’t just meet expectations—they quietly, elegantly surpass them. Pienza, Italy, is one of those places.

Located in the heart of the Val d’Orcia, this small Renaissance town isn’t just beautiful; it’s masterfully designed to be beautiful, the literal blueprint for the “ideal city” dreamed up during the 15th century. And somehow, centuries later, it still feels untouched, serene, and effortlessly cinematic.

I first visited Pienza, Italy, on a week long drive through Tuscany, thinking it would be a quick stop between Montepulciano and Montalcino. Instead, it completely captured me. Since then, I’ve returned a few times—sometimes for a lazy lunch and a sunset aperitivo, sometimes just to stroll the panoramic walls and feel time slow down.

Living in Italy has taught me how special places like this really are: places where daily life still happens inside a postcard-perfect frame.

In this Pienza guide, I’m sharing everything you need to know to experience Pienza at its best—where to stay, where to eat, what not to miss, and all the little tips that make a visit truly unforgettable.

*This Pienza travel guide may contain affiliate links, meaning I might make a small profit if you choose to book at no extra cost to you. This helps me to keep providing you with top-quality content for free.

When to Visit Pienza, Italy

Like with the whole of Tuscany, the best time to visit Pienza is in the shoulder seasons—spring (April to June) and autumn (September to October)—when the Tuscan countryside is at its most radiant and the town retains its slower, soulful rhythm.

In spring, the Val d’Orcia bursts to life with wildflowers and soft green hills, and local pecorino takes on its most delicate, herbaceous flavor. Autumn brings golden vineyards, truffle festivals, and that warm, amber light photographers dream of. These months offer the perfect balance of pleasant weather, fewer crowds, and rich seasonal experiences.

Summer is undeniably beautiful, with sunflower fields and long, lively evenings, but it also means intense heat and peak tourism. Winter, while quieter and more introspective, has its own offbeat charm—fog-draped mornings, cozy trattorias, and a glimpse of Tuscany without the gloss.

How to Get to Pienza, Italy

Tucked into the rolling hills of southern Tuscany, Pienza isn’t a place you stumble upon by accident. With no train station and no major highway, getting there takes a little effort, but that effort is richly rewarded with cinematic countryside and a simple kind of quiet beauty. Here’s how to make your way to Tuscany’s Renaissance gem.

By Car: Driving is by far the best—and most scenic—way to reach Pienza. Whether you’re coming from Florence (2 hours) or Rome (2.5 hours), a car gives you the freedom to roam the countryside, stop at vineyards or viewpoints on a whim, and explore nearby towns like Montepulciano, Montalcino, and San Quirico d’Orcia.

The drive from either city is relatively straightforward and utterly beautiful, with the final stretch winding through cypress-lined hills and golden wheat fields. Many parking lots are available just outside Pienza’s historic center, which is pedestrian-only. When visiting last winter, I parked here, with plenty of spaces available.

By Train: While Pienza Italy doesn’t have its own train station, you can take a train to Chiusi-Chianciano Terme, the nearest major rail hub (about 1.5 hours from Florence, 2 hours from Rome). From Chiusi, it’s about a 45-minute drive to Pienza—either by rental car or pre-arranged taxi. You can also take a train to Buonconvento or Montepulciano, but connections may be less frequent and car rentals more limited.

By Private Transfer: For those leaning into the luxury of slow travel (or just not keen on renting a car), a private transfer is an easy and comfortable option. Many boutique hotels and villas in the area will happily arrange a driver to pick you up from Florence, Rome, or nearby train stations.

It’s a great choice if you want to sit back, relax, and watch the Tuscan landscape unfurl without the navigation.

By Bike: For the romantics and the very fit: biking to Pienza is a possibility and a rite of passage for many cycling enthusiasts. The town sits along the scenic Strade Bianche, a network of gravel roads beloved by cyclists for their rolling hills and lack of heavy traffic. Be warned—this isn’t for the faint of heart. But if you’re up for the challenge, it’s one of the most rewarding (and poetic) ways to arrive.

Best Things to Do in Pienza, Italy

Stroll the Historic Center

The number one thing to do in Pienza is to get gloriously lost, though, truthfully, you won’t stay lost for long. The historic center is built around a single spine, Corso il Rossellino, which runs from Porta al Prato (also called Porta al Murello) on the west side straight through to Porta al Ciglio on the east.

Walking along it feels like moving through a living museum: Renaissance palaces, charming trattorias, boutique shops selling pecorino and ceramics, all flowing together in a way that feels impossibly harmonious.

Don’t miss Piazza Pio II, the heart of the village and a masterpiece of early urban planning. Framed by the grand Palazzo Piccolomini, the cathedral, and the town hall, the piazza is Pienza’s open-air living room, where locals and visitors alike gather for a coffee at Il Posto, a conversation, or simply to bask in the honeyed light that seems to have a special contract with this place.

Along the way, keep an eye out for the tiny romantic alleys branching off Corso il Rossellino—some of them are famously named Via dell’Amore (Street of Love) and Via del Bacio (Street of the Kiss). If ever there were streets made for a slow wander hand-in-hand, these are them.

Pop into Pienza Cathedral

Pienza Cathedral, or Duomo di Santa Maria Assunta, sits right at the center of town, anchoring Piazza Pio II with its simple yet striking Renaissance design. Built in the 15th century under the orders of Pope Pius II, it was part of his plan to transform Pienza into an ideal city of the Renaissance.

Unlike many Gothic churches of the time, the cathedral feels unusually bright and open inside, thanks to its large windows and clean architectural lines. It’s a place that feels welcoming rather than imposing, and a quick visit often turns into a longer one as you take in the quiet beauty of the space.

The interior is decorated with important 15th-century paintings by Sienese artists, and the overall feel is understated but elegant—very much in keeping with the humanist ideals Pope Pius II wanted to showcase.

While you’re there, don’t miss a visit to the crypt beneath the cathedral. It’s a much older, more intimate space, featuring original stonework, relics, and remnants from earlier periods. The crypt offers a more historic, almost hidden layer of Pienza’s story, making it well worth the short walk down, or so I’ve heard, as unfortunately, it was closed when I last visited.

Visit Palazzo Piccolomini and its Gardens

Just steps from the cathedral, Palazzo Piccolomini is one of Pienza’s highlights—and a direct window into the Renaissance dream. Built as the summer residence for Pope Pius II, the palazzo was designed by Bernardo Rossellino with a clean, harmonious layout that feels surprisingly modern for its time.

A visit here gives you a deeper sense of how Pienza was envisioned not just as a town, but as a model of ideal living.

Inside, you’ll find a series of stately rooms still furnished with period pieces, paintings, and even some original details from the 15th century. It’s easy to imagine the pope and his guests moving through these halls, with their high ceilings and views stretching across the Val d’Orcia.

But the real star is the hanging garden at the back of the palace. Perfectly symmetrical and opening out toward the countryside beyond, the garden feels like it was made for quiet walks and long, thoughtful conversations.

The view from the garden’s edge is one of the best I found in Pienza, Italy: an uninterrupted sweep of rolling hills, winding roads, and cypress trees that looks exactly like the postcards—and better. It’s a must-visit spot not just for the history, but for the simple, striking beauty that defines everything about Pienza.

Visit the Diocesan Museum (Palazzo Borgia)

Just off Piazza Pio II, the Palazzo Borgia houses the Museo Diocesano, a compact yet rich collection of religious art and artifacts spanning from the 13th to the 19th century. Originally gifted by Pope Pius II to Cardinal Rodrigo Borgia—who would later become Pope Alexander VI—the palace now serves as a museum showcasing the ecclesiastical heritage of the region.​

Inside, you’ll find an array of paintings, sculptures, liturgical objects, and illuminated manuscripts. Highlights include works by notable artists such as Pietro Lorenzetti and Luca Signorelli. The museum’s setting within the historic palace adds to its charm, with some rooms featuring original frescoes.

While the collection isn’t extensive, it offers a focused glimpse into the religious art and history of Pienza and its surroundings.

Walk the Panoramic City Walls

One of the simplest but most rewarding things to do in Pienza is to take a walk along its panoramic city walls. Stretching along the southern edge of town, the walls aren’t defensive battlements like in other Tuscan cities—they’re more like a promenade with a view, originally designed to frame the landscape as much as protect the town.

The path follows the outer curve of the historic center, offering breathtaking, uninterrupted vistas over the Val d’Orcia. Rolling hills, patchwork farms, winding country roads, and those iconic rows of cypress trees stretch out before you like a perfectly staged Renaissance painting. It’s the kind of view that feels almost too good to be real—and yet there it is, right at your feet.

The walk is easy and mostly flat, making it perfect for a leisurely stroll at any time of day, though early morning and late afternoon offer the best light for photography (and fewer people).

Sample Pienza’s Pecorino Cheese

If there’s one thing you absolutely cannot leave Pienza without doing, it’s tasting the local pecorino cheese. This isn’t just any pecorino—Pienza’s version is famously rich, nutty, and often aged to perfection in everything from walnut leaves to ash.

When I’m stocking up to take some home, I always head to La Taverna del Pecorino or Marusco e Maria. Both are old-school, no-frills spots that feel almost like stepping into someone’s pantry. You can sample different varieties—fresh, aged, truffle-infused (my personal weakness)—before committing. And they’ll vacuum-seal it for travel if you ask nicely, making it dangerously easy to overbuy.

If I’m just grazing around town, I’ll grab a seat at La Vecchia Bottega or Bar Il Casello. Both places do gorgeous pecorino boards, usually paired with local honey, jams, and a basket of rustic bread. I’ll order a spritz or a glass of local wine, claim a little outdoor table, and watch the slow, golden hum of Pienza unfold around me – Bar Il Castello is particularly good for this.

Visit the Surrounding Villages & Countryside

As perfect as Pienza is, part of the magic is what lies just beyond its walls. The Val d’Orcia is one of the most iconic landscapes in all of Italy—rolling hills, winding cypress-lined roads, and medieval villages that look like they haven’t changed in centuries. Setting aside at least a half-day (but ideally more) to explore the surrounding countryside is essential.

Some of my favorite nearby stops are Montepulciano, famous for its Vino Nobile and grand Renaissance palaces, and Montalcino, the home of Brunello wine and sweeping vineyard views. Both towns have a lively but laid-back feel, perfect for slow wandering, wine tastings, and long, leisurely lunches.

Bagno Vignoni is another must—a tiny spa village where the main piazza is literally a steaming hot spring. It’s like stepping into a medieval wellness retreat.

And honestly, one of the best ways to experience the countryside is just to drive without a plan. Take the strade bianche—the white gravel roads—through the fields and olive groves, pull over when you see a particularly stunning view (which will be often), and maybe stumble across a family-run trattoria you’ll talk about for years.

Where to Eat in Pienza

Pienza might be small, but it seriously overdelivers when it comes to places to eat and drink. Whether you’re craving a long, lazy Tuscan lunch, a casual spritz with a sunset view, or a quick coffee among locals, the town has plenty of gems tucked into its charming streets. Here’s where I always find myself going back to:

Sette di Vino – Cozy and full of character, this place is perfect for a relaxed, hearty meal. Don’t miss the Tuscan bean soup and anything featuring the local pecorino cheese—simple food, done incredibly well.

Trattoria Latte di Luna – A longtime Pienza favorite, known for its rustic Tuscan dishes and easygoing vibe. Think roast pork, hand-rolled pastas, and generous pours of house wine.

Trattoria da Fiorella – Small, welcoming, and serving up beautifully traditional plates. The menu is seasonal and local, with handmade pastas and slow-cooked meats you’ll be dreaming about later.

Idyllium – A stylish spot with a bit more of a contemporary twist, offering refined takes on Tuscan classics in a beautiful setting. Perfect if you’re looking for something a little special.

Bar Il Casello – One of my absolute favorite places for a sunset aperitivo. Grab a spritz or a glass of local wine, sit along the old walls, and watch the Val d’Orcia light up in gold. The views honestly don’t get any better than this.

La Posta – About as local as it gets. Right next to the Cathedral, this charming mash-up of tabacchi, post office, bar, and community hub is where locals come for their morning coffee, mid-morning gossip, or evening aperitivo. It’s casual, authentic, and full of everyday Pienza life.

Where to Stay

Pienza may be a small Renaissance jewel, but it offers a range of luxurious accommodations that blend historic charm with modern comforts. That said, most travelers here visit for the day or half a day before moving on but it might be well worth it to stay the night.

La Bandita Townhouse – Located on Corso il Rossellino, La Bandita Townhouse is a boutique hotel that combines rustic charm with contemporary design. Set in a former convent, it features minimalist interiors, exposed stone walls, and a cozy lounge with a library and vinyl collection. The on-site Townhouse Caffe offers seasonal Italian dishes, making it the place to stay in town.

Monastero Sant’Anna in Camprena – Just north of Pienza in the countryside, you’ll find this luxury property in a converted monastery. With Renaissance frescoes by Sodoma, simple, almost monastic rooms, and sweeping countryside views.

L’Olmo – Situated near Monticchiello, L’Olmo is a restored farmhouse offering a serene retreat with just seven suites. The property boasts a heated outdoor pool, beautifully landscaped gardens, and interiors that reflect classic Tuscan style. I love this property for its privacy and panoramic countryside views.

Top Tours for Visiting Pienza

While Pienza is perfect for slow, unstructured wandering, sometimes a guided experience can reveal an entirely new layer of the town and its stunning surroundings. Some fantastic tours dive deeper into what makes this part of Tuscany so special.

From walking tours that uncover hidden corners of the historic center to countryside adventures through the Val d’Orcia’s rolling hills, here are some of the best ways to experience Pienza with a little extra insider knowledge.

Top Tips for Visiting

Pienza, Tuscany is the kind of place that rewards those who move a little slower, look a little closer, and leave room for serendipity. To help you make the most of your time here, here are a few insider tips I’ve picked up after multiple visits (and a few mistakes along the way):

Time your visit carefully. Early morning and late afternoon are magical in Pienza—the town glows in the soft light, the streets are quieter, and you’ll have the panoramic walls practically to yourself. Midday can bring tour groups, especially in summer, and many businesses close in the early afternoon for siesta.

Stay overnight if you can. Many just breeze through on a Val d’Orcia day trip, but staying overnight lets you experience the town when it’s most peaceful, after the buses leave and the locals come out for their evening passeggiata.

Book ahead for meals. In high season (spring, early fall, and summer weekends), the best trattorias and restaurants book up fast. A quick call or a message a day ahead can save you from missing out on some incredible meals.

Pack comfortable shoes. Pienza’s stone streets are charming but unforgiving—leave the flimsy sandals behind and opt for something you can stroll in comfortably.

Taste the pecorino early and often. Don’t wait until the end of your trip to sample the town’s famous cheese—you’ll want time to go back for more (trust me on this).

Use Pienza as a base. It’s perfectly located for easy drives to Montepulciano, Montalcino, Bagno Vignoni, and countless hilltop villages. Renting a car gives you the freedom to explore on your own schedule.

Bring cash. While most places accept cards, a few small shops, cafes, and parking lots are still cash-only, especially in the countryside.

Expect slower service—and embrace it. Meals here are meant to be savored, not rushed. Lean into the slow rhythm of Tuscany. Order another glass of wine. Watch the sunset. That’s the whole point.

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Ready for your trip to Pienza, Italy? Let me know your questions and comments below, and how you got on with these best things to do in Pienza, I’d love to hear from you.

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