Found within the panoramic backdrop of the Val d’Orcia, a UNESCO World Heritage site in central Italy, lies Pienza, a small but quintessential Tuscan treasure. Boasting a storied past and an architectural canopy inspired by the Renaissance ideals of urban living, Pienza offers many experiences that harmoniously blend art, history, and gastronomy.

During my recent travels through southern Tuscany, the charm of Pienza was unmistakable, with its embrace of pecorino cheese, the intricate details of its palazzi, and inviting cobblestoned streets that conjure a bygone era.

As a town epitomizing the idyllic Italian countryside, Pienza provides a serene escape from the bustle of larger cities. Imagine strolling along the intact city walls with a gelato in hand, absorbing the views of the rolling hills dotted with cypress trees and perhaps indulging in an impromptu picnic featuring the region’s freshest produce while basking under the Tuscan sun.

Just take a look at this vantage point that I took from above. Not only these, but you’ll also find my photography throughout this guide from my visit. I wanted to take a picture of EVERYTHING, so much so that I ran out of battery for all my cameras but nighttime.

My family’s time here was a dance with the delights of slow travel—each step a vignette of culture and leisure. Beyond its picture-perfect scenery, Pienza’s allure lies in its human scale.

Don’t take my word for it. Experience all these great things to do in Pienza with me from the video footage I took from visiting below. All from the ViaTravelers YouTube Channel.

1. Pienza Cathedral

Address: Piazza Pio II, 2, 53026 Pienza SI, Italy

During our stay in the heart of Tuscany, the Pienza Cathedral, or l Duomo di Pienza, officially known as the Cathedral of Santa Maria Assunta, commanded our attention. Consecrated in 1462, this 15th-century masterpiece, designed by the architect Bernardo Rossellino, exemplifies Renaissance architecture. Built upon the orders of Pope Pius II, it’s exceptionally well preserved.

The intricate details immediately capture your gaze as you walk into the Cathedral. Rosy-hued travertine columns stretch towards the heavens, framing a wealth of Renaissance artwork adorning the church. The altarpieces, crafted by artists such as Giovanni di Paolo and Matteo di Giovanni, hold stories of religious significance—perfect pauses for reflection.

To truly appreciate the cathedral, allot time to explore its corners. If your interest lies in history, descend into the crypt, where remnants from the Church of San Giovanni unveil a period long past. The cathedral is more than a religious site; it’s a cultural gem that connects you with Pienza’s storied legacy.

The Pienza Cathedral is manageable to navigate for families, even with a stroller. Engaging for adults yet not overwhelming for children, it offers a serene retreat from the Tuscan sun.

And for those who appreciate a slice of history encased in tranquility, Pienza’s spiritual and historical center here will resonate deeply. Remember to revel in the cathedral’s tranquil ambiance and think of the countless who have walked these hallowed halls before you.

2. Palazzo Piccolomini

Address: Piazza Pio II, 2, 53026 Pienza SI, Italy

Palazzo Piccolomini is a true gem located in the heart of Pienza. Here’s how you can make the most of your visit to this famous historic site. While exploring Pienza with my family, we discovered Palazzo Piccolomini, just around the corner from our hotel (the renowned Relais Il Chiostro di Pienza). If you love porticos, this is your heaven on Earth.

We learned that this was the summer residence of Pope Pio II, which stands as one of the earliest examples of Renaissance architecture. Designed by Bernardo Rossellino, a student of the illustrious Leon Battista Alberti, the palazzo was inspired by Florence’s Ruccellai Palace.

Experience the palazzo’s square design, with stone and marble features that lend it an air of refined elegance. Each level showcases rows of windows, displaying the harmonious symmetries beloved by Renaissance architects. The interiors are no less impressive, housing various rooms once used by the pope and his court.

As you step into the central courtyard, you’re sheltered by a portico, perfectly framing the picturesque views of Val d’Orcia—a UNESCO World Heritage site. This portico also provides a cool respite on sun-drenched days, making it an ideal spot for family visitors seeking shade.

On my visit, it was awe-inspiring to stand where a pope once stood and to share that moment with my wife and daughter. Book your tickets, as trips here are popular and can sell out quickly. Remember that most tickets offer a full refund if you cancel at least 24 hours before your scheduled tour, a little travel hack that offers flexibility in your itinerary.

See Related: Italy Travel Guide: Travel Tips for Visiting

3. Piazza Pio II

Piazza Pio II is the square that underpins the most notable historical sites of the city: Pienza Cathedral, Palazzo Piccolomini, and Diocesan Museum (Palazzo Borgia). As you stroll into this trapezoid-shaped square, you are met with an architectural harmony envisioned by Enea Silvio Piccolomini, who became Pope Pius II. His legacy is evident in the balance and beauty of the piazza’s surrounding structures.

Immerse yourself in the local stories of the main square here; every building whispers a slice of history. Spend your morning embracing the rare tranquility as Pienza awakens, the soft light casting the cathedral in a warm glow, ideal for photographers seeking that perfect Tuscan shot. For families, this is a peaceful space for children to explore without worrying about bustling city streets.

Indulge in an artisanal gelato while seated on a bench, and absorb the authenticity of small-town Italy that remains largely untouched by time. Should you visit in the off-season, you’ll share this experience with just the locals, allowing for a more personal encounter with Tuscany’s culture. Take a moment to look at the historic water well in the square. It’s beautiful.

Before leaving, climb to the top of Palazzo Comunale’s bell tower. The panoramic view of the Val d’Orcia is an unforgettable sight—a perfect crescendo to your Pienza visit.

4. Val d’Orcia

While wandering Pienza, your senses are rewarded by the quintessential Tuscan backdrop of Val d’Orcia. The landscapes here are a seamless patchwork of rolling hills dotted with cypress trees and vast sun-soaked valleys.

Val d’Orcia offers countless photographic moments, especially during the golden hour. Position your camera low to capture the undulating contours of the land.

Insider Tip: Ask local Pienza residents for their favorite spots in Val d’Orcia while dining or having a glass of wine at a local wine bar for a personal touch to your exploration.

6. Go on a culinary adventure

An epicurean journey in Pienza is absolutely required. This is where the flavors of Tuscany come to life. Experience the town’s renowned pecorino di Pienza cheese, savor traditional Tuscan dishes, and wander through charming local markets.

Pecorino Cheese Tasting

Pienza is synonymous with pecorino cheese, a savory delight that you’ll find featured in many local dishes or enjoyed on its own. Sample different pecorino ages — from the fresher ‘giovane’ to the matured ‘stagionato’. Cheese lovers must visit a local caseificio where you can taste and learn about the cheese-making process from the local artisans.

• Caseificio Cugusi: A short drive from Pienza, indulge in cheese tastings while overlooking the Tuscan hills.
• La Taverna di Re Artù: Offers a variety of pecorino cheese paired with honey and jams.

Authentic Tuscan Cuisine

Find yourself indulging in the rich, homey flavors of authentic Tuscan cuisine in Pienza. The town is dotted with family-run trattorias where recipes have been passed down for generations. Don’t miss out on trying pici, a hand-rolled pasta commonly served with wild boar ragù or garlic sauce.

• Trattoria da Fiorella: Known for its pici pasta and local wines. This is where we ate, and it was unbelievable. That’s the pici you’ll see above.
• Sette di Vino: A local favorite where traditional dishes and a warm atmosphere invite you to linger.

Local Food Markets

Wandering through Pienza’s local food markets is a feast for the senses. Fresh produce, truffles, and artisanal goods are here — perfect for a picnic with a view of the Val d’Orcia. Visit the Pienza Market on Friday mornings for the best selection of local products.

Remember that in Pienza, dining is not just about the food but the experience. Take your time, sip a glass of wine, and let the flavors of this quaint town transport you. This is where you slow down time, not run around trying to see every last corner. The surrounding landscape, food, and wine ARE your attractions.

See Related: Incredible Reasons to Visit Italy This Year

7. Take in the scenery

While exploring the quaint town of Pienza during my Tuscany adventures, I discovered that immersing oneself in the picturesque landscape is an absolute must. Since the old town is perched on a hill, it provides panoramic views of the Val d’Orcia, making it a paradise for photographers. I found myself at dawn, camera in hand, capturing the soft morning light as it painted the hills a golden hue.

Palazzo Piccolomini’s Garden is ideal for framing the perfect shot of the region’s undulating countryside. Steal a chance for an aerial perspective of the surrounding landscape; the views are enchanting during the golden hour.

8. Visit the Diocesan Museum (Palazzo Borgia)

Address: Corso il Rossellino, 30, 53026 Pienza SI, Italy

While you wander the Piazza Pio II, take a moment to explore the artistic and historical treasures housed within the town walls at the Diocesan Museum at Palazzo Borgia. This museum presents a unique opportunity to connect with the town’s religious and cultural past.

And as you meander through the museum’s rooms—once part of the palatial residence of Cardinal Rodrigo Borgia—you’ll be greeted by an impressive array of sacred art. Notable is the Madonna di Monticchiello, an awe-inspiring painting by Pietro Lorenzetti, its timeless beauty resonating with devotees and art lovers.

While exploring with your toddler, remember that little legs tire easily; the museum’s compact size is perfect for a short and engaging visit, and stroller-friendly paths ensure a comfortable family experience.

This attraction is integral to understanding Pienza, showcasing why this Renaissance town is more than just stunning panoramas—it’s a place where history’s layers are meticulously preserved for all to appreciate.

9. Shop for Local Tuscan Items

When visiting Pienza, immersing yourself in the local shopping scene is essential. Walking through the streets of a charming village lined with charming boutiques and specialty shops feels like a treasure hunt for authentic Tuscan goods, such as hand-painted ceramics and textiles, and exquisite leather products.

You can’t leave without sampling the town’s renowned pecorino cheese, fragrant and sourced from the local sheep’s milk. The cheese shops often provide tastings, and I promise the rich flavors will have you packing a wedge or two for the journey home.

Beyond cheese, explore the food shops for dried porcini mushrooms and bottles of rich Tuscan olive oil—a perfect pairing for home-cooked Italian meals.

Be sure to check out the Artemisia Art Gallery: This gallery is a delightful detour for enthusiasts. Here, local artists display their works, often reflecting the Tuscan landscape and culture. It’s an intimate experience; you might even catch an artist in action.

10. Wine Tasting Experiences

Venturing through the winding streets, you can’t help but be lured by the scent of Pienza’s local vineyards that beckon a tasting journey. Join a guided wine tour, often starting directly in town, which leads you into the encompassing hills known for their robust Sangiovese grapes. The intimate knowledge shared by local sommeliers is both enlightening and captivating.

This has many benefits, such as allowing you to sample a flight of the region’s best reds and whites and walk among the rows of vines where the magic begins.

See Related: Best Wine Regions in Italy to Visit

11. Day Trips from Pienza

A short drive from Pienza, Siena is recognized for its medieval cityscape, iconic Piazza del Campo, and the historic Palio horse race. Immerse yourself in gothic architecture and indulge in the local culinary delights.

Renowned for the Brunello di Montalcino wine, this charming hilltop town is perfect for a day trip. Visit the fortress for panoramic views, and don’t miss the chance to taste the prestigious local wine.

Another gem within reach, Montepulciano, offers a blend of Renaissance architecture and viticulture. Meander through its ancient streets before enjoying a glass of Vino Nobile di Montepulciano at a local enoteca.

12. Walking, Hiking and Biking

Your journey through the Val d’Orcia is incomplete without taking advantage of the walking trails that meander through the sprawling countryside. The Via Francigena, an ancient road and pilgrim route from France to Rome, offers a historical path where every step echoes the past.

Throughout my family and a short walk there, the soft curves of the Tuscan hills unfolded before us, dotted with strategically planted cypress trees that added to the tranquil atmosphere.

• Sentiero dell’Idolo: A trail presenting breathtaking views, suitable for avid hikers and leisurely walkers like my toddler, who enjoyed the open air.
• Podere San Gregorio: A picture-perfect spot where the iconic Tuscan landscape greets you, ideal for family picnics amidst the olive groves.

For a challenge, take your bike to the hilltop town of Montepulciano. The Montepulciano Route may test your stamina, but the views and the sense of achievement are incomparable. Pause to enjoy a well-deserved gelato upon arrival.

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