Uncover the Best Things to Do in Pienza on Your Journey

Pienza isn’t just another hilltop town in Tuscany, it feels built for slow walks, long lunches, and “I’ll just take one more photo” moments. Born from Pope Pius II’s dream of the perfect Renaissance town, it still delivers on that promise with golden stone streets and views that roll forever. Between cheese shops that smell like heaven, trattorias that never let your glass go empty, and Tuscany wine tours just around the corner, this little gem knows how to spoil you. Ready to dive into the best things to do in Pienza? Bring your appetite, your camera, and maybe some extra room in your suitcase.

What are the best things to do in Pienza?

Stroll through Piazza Pio II

Start your walk in Piazza Pio II, the showpiece of Pienza and a masterpiece of Renaissance design. Commissioned by Pope Pius II and brought to life by architect Bernardo Rossellino in the 15th century, this square is all about balance and beauty. The cathedral’s elegant façade sets the scene, while palaces line the edges with perfect symmetry. Pause here, take in the geometry, and snap a photo that feels straight out of an Italian art book.

Visit Palazzo Piccolomini

On one side of Piazza Pio II, Palazzo Piccolomini steals the show with its hanging gardens overlooking the Val d’Orcia. Step through the courtyard, wander rooms that still echo the Renaissance, and head down to the wine cellar that ties the palace to Pienza’s vineyard heritage. The mix of history, design, and those jaw-dropping views makes this palace a highlight you’ll remember long after you leave.

Step into Pienza Cathedral

The Duomo di Pienza is a striking mix of Gothic lines and early Renaissance elegance, standing tall at the heart of the town. Step inside to find luminous frescoes and paintings by masters like Luca Signorelli and Pietro Lorenzetti, each one adding layers of color and story to the walls. Don’t skip the crypt below, a quiet, atmospheric space that reveals the spiritual soul of this 15th-century masterpiece. Visiting the cathedral is one of the essential things to do in Pienza, blending art, history, and timeless beauty.

Walk Via del Casello for the best views of Val d’Orcia

If you’re chasing the best views of the Val d’Orcia, make your way to Via del Casello. This panoramic street runs along Pienza’s ancient walls and opens onto a landscape of rolling hills dotted with cypress trees, olive groves, and golden wheat fields. Come at sunset for a glow that makes every photo unforgettable, a moment that easily ranks among the must-see things to do in Pienza.

Explore the Palazzo Borgia Diocesan Museum

Tucked beside the Duomo, Palazzo Borgia holds a small yet fascinating museum that feels like stepping back into Pienza’s spiritual history. Inside, sacred art, liturgical relics, and frescoes line the rooms with quiet elegance. Once gifted by Pope Pius II to the town’s bishop, the palace still carries the weight of centuries, offering a glimpse into the deep religious roots that shaped Pienza.

Head to Porta al Ciglio and the City Walls

Step into Pienza through Porta al Ciglio, one of the gateways piercing its ancient walls. Crossing under the arch feels like slipping straight into the past, with cobbled streets and narrow alleys unfolding ahead. As you wander, you’ll spot ceramic shops, balconies spilling with flowers, and corners that look like they’ve been waiting centuries for your camera. Pienza remains one of Italy’s most beautifully preserved small towns, and walking through this gate is the perfect way to begin exploring it.

Wander to the Church of San Francesco

This 13th-century church may not dazzle with size, but its charm lies in the details. Step through the doorway and you’re met with centuries-old frescoes, worn yet beautiful, and a silence that feels almost timeless. It’s a glimpse of Pienza before the Renaissance makeover, modest, spiritual, and deeply rooted in its monastic past.

What are the best things to do around Pienza?

Visit the medieval treasures of Bagno Vignoni

Just 15 minutes from Pienza, Bagno Vignoni takes you into another world. Here, the main square isn’t a piazza but a steaming thermal pool, surreal and unforgettable. Wander stone alleys, soak in warm waters, then stretch out a Tuscan lunch while the Val d’Orcia rolls out in front of you. Afternoons here slow down to their own rhythm, making it easy to forget schedules and stay longer than planned.

Wander through Montepulciano

18 minutes from Pienza, Montepulciano rises above the Tuscan countryside with a skyline of towers and Renaissance palaces. Stroll down Via del Corso, where elegant façades hide cafés, artisan boutiques, and centuries of stories carved into stone. Piazza Grande, with its monumental buildings and lively atmosphere, is the perfect stage to soak in the spirit of this hilltop town. Of course, no trip is complete without exploring the famous Montepulciano wineries, where history and tradition meet in every sip.

Discover the best things to do in Montepulciano and let this Renaissance gem steal your heart.

Explore the legendary Montalcino

Just 15 miles from Pienza, Montalcino delivers everything you imagine from a Tuscan hilltop town. Stone houses line winding streets, the 15th-century fortress towers above the rooftops, and views spill across vineyards as far as the eye can see. This is the land of Brunello, and exploring the famous Montalcino wineries is an experience no traveler should miss. Between tastings, slow walks, and sunlit piazzas, the town captures the essence of southern Tuscany.

For more inspiration, check our guide to the best things to do in Montalcino and see why this stop is unmissable on any Tuscany itinerary.

Step into the magic of aged Tuscan vintages

Visit a hidden cellar where old vintages whisper stories of seasons long past. At this small, biodynamic wine cellar in Montepulciano, the wine isn’t just tasted, it’s felt. You’ll descend into Evelina’s caveau, sample aged bottles side-by-side with the newest releases, and enjoy a light lunch that complements every sip. Between the warm hospitality, museum-like setting, and views out over the Tuscan hills, this experience isn’t just about wine, it’s about connection, tradition, and slowing down.

Uncover biodynamic Sangiovese in an intimate cellar

At this family-run winery in the rolling hills around Montepulciano, you’ll walk through organic, biodynamic vineyards and down into a cellar where Sangiovese is made with minimal intervention. The atmosphere is warm, intimate, and real. This is a wine you can sense with all your senses. Let a tasting here show you what Montepulciano wineries do best: authentic flavor, deep connection to the land, and a story in every glass.

Drive the panoramic wine route to Chianciano Terme

A Tuscany road trip isn’t complete without rolling down the winding route from Pienza to Chianciano Terme, just 30 minutes away. The drive itself is pure scenery, golden wheat fields, olive groves, and hilltop villages that seem to appear out of nowhere. Once in Chianciano, trade vineyards for thermal spas and let the mix of wellness and history take over your day. Between quiet piazzas, Renaissance corners, and views stretching across the Val d’Orcia, this stop feels like a gentle pause in the middle of your Tuscan adventure.

Sip local in a unique place

Wander through rolling vine-clad hills and arrive at Fattoria Svetoni, this elegant wine resort where history isn’t just preserved, it’s lived. At this family farm around Montepulciano, centuries of Sangiovese vines stretch out from golden fields to an old cellar where you’ll taste wines rooted in tradition. Between the rustic charm of the courtyard, sweeping views, and warm hospitality, every moment here slows you down and makes you appreciate the land’s quiet power.

Good to know before visiting Pienza