Montepulciano may be small, but it’s bursting with history, charm, and unforgettable views. Perched high on a hill between Val d’Orcia and Val di Chiana, this medieval town is best known for its wine. But there’s much more to explore beyond the vineyards!
Here’s your essential guide to the must-see sights in Montepulciano, perfect for a first-time visitor or anyone looking to rediscover the magic.
Piazza Grande: The Heart of Montepulciano
This majestic square is the town’s crown jewel. Surrounded by Renaissance palaces and the Duomo, Piazza Grande feels like stepping into a movie scene—literally! The Twilight Saga: New Moon filmed scenes here.
Don’t miss:
- Climbing the Torre di Pulcinella or Palazzo Comunale tower for 360° views
- Sipping coffee or wine at an outdoor café
- Visiting during the Bravio delle Botti race in August
Montepulciano Cathedral (Duomo di Montepulciano)
The Duomo, officially called Cattedrale di Santa Maria Assunta, anchors Piazza Grande. Its simple facade hides a stunning interior featuring the 15th-century Assumption of the Virgin triptych by Taddeo di Bartolo.
Tip: It’s free to enter, and a lovely place to cool down or reflect.
The Underground Wine Cellars
Montepulciano is built on volcanic rock, making it ideal for historic underground wine cellars. Many of them are free to enter and offer tastings of Vino Nobile di Montepulciano, the town’s signature wine.
Top picks:
- Cantina De’ Ricci – A cathedral-like cellar experience
- Contucci Cantine – Run by one of Montepulciano’s oldest families
- Talosa – Offers tours beneath Renaissance-era buildings
- Make a reservation if you’re visiting during the high season.
Church of San Biagio: A Renaissance Masterpiece
Located just outside the town walls, San Biagio is one of the most iconic churches in Tuscany. Built in the 16th century, this travertine temple sits peacefully in the countryside.
Why visit:
- The architecture is breathtaking inside and out
- You’ll get a beautiful panoramic view of Montepulciano from below
- The church is often surrounded by blooming flowers in spring
The City Walls and Gates
Take time to explore Montepulciano’s historic gates, like Porta al Prato and Porta delle Farine. Walking along the town walls gives you stunning views of the valleys below.
Don’t miss: The views at Piazzale di San Francesco, especially at sunset.
Corso Street: Montepulciano’s Main Shopping and Strolling Street
The Corso is the town’s main artery, winding from Porta al Prato to Piazza Grande. It’s lined with artisan shops, gelato spots, wine stores, and boutiques.
Must-stops:
- Delicatessens selling local pecorino and truffle products
- Handmade ceramic shops
- Local linen and leather boutiques
Local Museums and Cultural Spots
Want to dive deeper into Montepulciano’s history?
Museo Civico (Civic Museum): Housed in the Palazzo Neri Orselli, this museum showcases Etruscan artifacts, religious art, and Renaissance works.
Cantiere Internazionale d’Arte: An annual art and music festival (held in July) that includes performances and exhibitions across the town.
Bonus: Hidden Gems Worth Seeking Out
The Medici Fortress (La Fortezza): Now home to the Enoliteca, a sleek wine-tasting venue inside a centuries-old fortress.
Church of Sant’Agostino: Just past Porta al Prato, known for its rose window and peaceful interior.
The Belvedere: A perfect scenic overlook near San Biagio.
Montepulciano invites you to slow down, sip slowly, and look closely. It’s not just about checking landmarks off a list, it’s about soaking in the atmosphere, talking with local artisans, and enjoying every corner of this hilltop haven.
No matter how long you stay, these highlights will give you a rich and memorable experience of Montepulciano.
