Vacation in Tuscany: What to Do in Montepulciano

 Rolling hills, Renaissance architecture, golden light, and world-famous wines — welcome to Montepulciano, one of the most authentic and charming destinations for a vacation in Tuscany. Whether you’re here for a few days or just passing through, this hilltop town in southern Tuscany offers a perfect blend of history, beauty, and unforgettable experiences.


In this guide, we’ll walk you through what to do in Mont


epulciano, when to go, and how to enjoy the best of Tuscan life.

🗓️ When to Visit Montepulciano

Every season in Montepulciano has its magic:

  • Spring (March–May): Green landscapes, wildflowers, mild weather

  • Summer (June–August): Festivals, open-air concerts, vibrant streets

  • Autumn (September–October): Harvest time, grape picking, truffle menus

  • Winter (November–February): Peaceful vibe, Christmas market, fewer crowds

For most travelers, spring and autumn are ideal — warm days, cooler evenings, and rich seasonal colors.

🏛️ What to See and Do

1. Stroll Through the Old Town

Montepulciano is a town made for walking. From the lower gates to the hilltop Piazza Grande, every step brings a discovery.

Don’t miss:

  • Via di Gracciano nel Corso: the main shopping street with artisan boutiques

  • Piazza Grande: the scenic central square surrounded by historic palaces

  • Palazzo Comunale: climb its tower for panoramic views over the Tuscan hills

  • Duomo di Montepulciano: impressive Renaissance church with a serene interior

Walk slowly, stop for an espresso, and enjoy the beauty around every corner.

2. Taste World-Class Wines

Montepulciano is the birthplace of Vino Nobile di Montepulciano, one of Italy’s first DOCG wines. Deep, elegant, and aged in oak, it’s a must for wine lovers.

Where to go for tastings:

  • Cantina Contucci: historic family-run cellar beneath a Renaissance palace

  • De’ Ricci Wine Cellar: breathtaking underground arches and tastings

  • Avignonesi (nearby): organic wines with countryside tours and pairing lunches

You can also stop at enotecas in town to buy bottles or sample by the glass.

3. Visit the Temple of San Biagio

A short walk outside the walls takes you to the stunning San Biagio Church, a 16th-century Renaissance masterpiece set among olive trees and vineyards.

Why it’s special:

  • Built from golden travertine stone

  • Designed with perfect symmetry and harmony

  • Quiet and spiritual atmosphere with incredible photo ops

It’s ideal for sunset strolls or a mid-afternoon pause.

4. Dine in Style at Osteria Fra L’Altro

No vacation in Tuscany is complete without a truly memorable meal. In Montepulciano, that means booking a table at Osteria Fra L’Altro.

Located in a peaceful alley near the center, this elegant restaurant blends Tuscan tradition with creative flair.

Menu highlights:

  • Homemade pasta with saffron and wild herbs

  • Slow-roasted pork or duck with seasonal sides

  • Desserts made with local Vin Santo and fruits

  • Wine list featuring the best of Vino Nobile, Chianti, and beyond

The ambiance is ideal for couples, food lovers, or anyone celebrating life with good taste.

5. Explore Local Artisan Culture

Montepulciano is full of small shops where local artisans create and sell their crafts:

  • Ceramics and terracotta from nearby workshops

  • Olive oil, honey, and jams from family farms

  • Textiles and leather goods handmade with care

Shopping here supports local traditions and makes for meaningful souvenirs.

6. Enjoy the Landscape

Montepulciano sits at the crossroads of Val d’Orcia and Valdichiana, two of Tuscany’s most picturesque valleys.

Ideas for nature lovers:

  • Hike or bike along country roads between vineyards and cypress trees

  • Rent a Vespa for scenic drives through Pienza, Monticchiello, or Bagno Vignoni

  • Pack a picnic and enjoy a lazy afternoon in the countryside

Autumn and spring are especially breathtaking with vibrant colors and cool breezes.

7. Attend a Local Festival

Montepulciano has a rich calendar of events that offer a deeper look into Tuscan life.

Top events:

  • Bravio delle Botti (August): medieval parade and barrel-rolling competition

  • Cantiere Internazionale d’Arte (July): music, dance, and theater in historic spaces

  • Christmas Market (December): festive lights, stalls, and winter food specialties

These events attract both locals and visitors and make your stay truly special.

🛌 Where to Stay

Montepulciano offers accommodations for every style:

  • Boutique hotels in the old town

  • Agriturismos (farm stays) with pools and views

  • Apartments and B&Bs for a homier feel

Wherever you stay, you’re always close to wine, history, and unforgettable views.

🍷 Featured Dining: Osteria Fra L’Altro

Osteria Fra L’Altro
 Via Borgo Buio 10, Montepulciano (SI), Italy
 🌐 www.fralaltro.it
🍷 book your table online 
📞 +39 0578 778188

Elegant, cozy, and run with passion — the perfect place to end a Tuscan day.


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