Nestled in the Tuscan hills, Montepulciano is a charming hilltop town known for its Renaissance architecture, sweeping countryside views, and world-famous Vino Nobile wine. It’s a perfect stop if you’re exploring Tuscany wine tours or simply looking for a relaxing day surrounded by vineyards and history. From strolling the old streets and tasting wine in underground cellars to enjoying local food with a view, there are plenty of things to do in Montepulciano that blend culture, flavor, and classic Italian beauty.
Best things to do in Montepulciano
Wander at Piazza Grande
Start your visit in Montepulciano at Piazza Grande, the historic and cultural heart of the town. Surrounded by elegant Renaissance buildings, the Palazzo Comunale, and the Cathedral of Santa Maria Assunta, this main square sets the scene with its timeless charm. Climb the clock tower for panoramic views of the Tuscan countryside, stretching out over vineyards and valleys. It’s one of the best photo spots in town.
Tour the Clock Tower at Palazzo Comunale
Climb the iconic clock tower of the Palazzo Comunale on Piazza Grande for unbeatable views over Montepulciano and the Val d’Orcia. Inspired by Florence’s Palazzo Vecchio, this elegant stone palace anchors the town’s main square and brings Renaissance grandeur to the hilltop skyline. The climb may be steep, but the reward is a panoramic glimpse of tiled rooftops, vineyards, and rolling Tuscan hills, perfect for a quiet moment or your next postcard shot.
Visit the Fortress of Montepulciano
The 14th-century fortress in Montepulciano has been beautifully restored and now blends history with modern charm. Just a short walk from Piazza Grande, it hosts seasonal events, wine exhibitions, and a peaceful garden café where you can enjoy a glass of Tuscan wine surrounded by views of the countryside. It’s one of the best spots in town to unwind and soak in Montepulciano’s timeless beauty.
Uncover the beauty of San Biagio
Just outside of town lies the Temple of San Biagio, an exquisite example of Renaissance architecture in Tuscany. Surrounded by cypress trees and set against the rolling hills of the Val d’Orcia, this church, designed by Antonio da Sangallo the Elder, is both peaceful and iconic. A visit here is one of the best things to do in Montepulciano, offering stunning views and a quiet moment to soak in the beauty of the Tuscan countryside.
Taste aged elegance in the heart of Montepulciano
Step into a candlelit cellar in Montepulciano and experience a vertical tasting of old vintages, comparing two exceptional aged wines with a current release. This immersive 2-hour journey takes place in a beautifully preserved caveau, offering a rare look at biodynamic winemaking and family heritage. Alongside the tasting, enjoy a light lunch featuring local flavors that enhance the character of each glass. Perfect for wine enthusiasts looking to deepen their palate and knowledge, this experience blends tradition, storytelling, and the true spirit of Tuscany.
Best things to do around Montepulciano
Visit the town of Pienza
Just 15–20 minutes from Montepulciano, the hilltop village of Pienza is a Renaissance jewel in the heart of Tuscany. Famous for its harmonious architecture and dreamy piazzas, it’s the perfect spot for a leisurely stroll, a slice of Pecorino cheese, or a glass of wine overlooking the Val d’Orcia. Explore artisan boutiques, grab lunch on a terrace with panoramic views, and soak up the slower pace. If you’re based in Montepulciano, visiting Pienza is one of the easiest and most rewarding short trips to round out your Tuscan experience.
Enjoy biodynamic Sangiovese with a minute to spare
12 minutes from the center, step into the peaceful vineyards of Montepulciano for a relaxed tasting of biodynamic wines at a small local estate. In just under 1.5 hours, you’ll taste three natural wines made with Sangiovese grapes and learn how the winery works with nature instead of chemicals. It’s a great stop if you’re exploring Tuscany and want a simple, authentic wine experience in a calm setting.
Drive to Cortona
About 35 minutes from Montepulciano, Cortona is a postcard-worthy Tuscan town perched above the Val di Chiana. Steeped in Etruscan history and known for its cinematic charm, Cortona is perfect for a relaxed afternoon. From hilltop wine tastings to artisanal shops and panoramic walks, there’s plenty to fill your time. If you’re planning your trip, check out the best things to do in Cortona Italy, the views, the wine, and the peaceful pace are worth it.
Explore the hilltop charm of Montalcino
Montalcino is a must-visit destination in southern Tuscany, known for its rich history, peaceful streets, and world-class wine. Perched above the rolling hills of the Val d’Orcia, this medieval town is the birthplace of the prestigious Brunello di Montalcino. As you stroll through the cobbled alleys, you’ll find panoramic viewpoints, ancient fortresses, and welcoming enotecas offering tastings of local reds. Montalcino wineries are among the best in Italy, with many offering cellar tours and guided tastings just outside the town center.
For a full experience, plan time to relax in a wine bar, explore the fortress, and discover the top things to do in Montalcino, from wine museums to scenic drives through the vineyards.
Discover Lake Trasimeno’s nature
Around 45 minutes from Montepulciano, Lake Trasimeno in Umbria offers a refreshing escape into nature without straying too far from Tuscany’s beloved wine and food culture. The area is dotted with wine estates and cozy wine bars where you can try regional varieties beyond the famous Vino Nobile di Montepulciano. It’s a great spot for hiking trails, boat rides to the lake’s islands, or sipping a chilled glass of white wine with lake-caught fish. If you’re building your itinerary and exploring the best things to do in Montepulciano, a scenic detour to Lake Trasimeno adds variety to your Tuscan adventure.
Good to know before visiting Montepulciano
Is Montepulciano worth visiting?
Absolutely. Montepulciano is a gem of southern Tuscany, famous for its medieval and Renaissance architecture, breathtaking hilltop views, and rich food and wine traditions. It’s less crowded than other Tuscan towns like Florence or Siena, offering a more authentic and relaxed experience. It’s especially well known for its Vino Nobile di Montepulciano wine, making it a must-visit for both culture lovers and wine enthusiasts.
What are the top things to do in Montepulciano?
Top activities include exploring Piazza Grande and its impressive Palazzo Comunale, visiting the Duomo, and touring the underground wine cellars of historic wineries like Cantina Contucci and De’ Ricci. Don’t miss the stunning views from the city walls and a visit to Tempio di San Biagio, a Renaissance church just outside the town center. Shopping for locally made leather and ceramics is also popular.
What can I do in Montepulciano for a day?
Start your day with a coffee in Piazza Grande, followed by a visit to the Cathedral and Palazzo Comunale’s panoramic tower. Spend the afternoon wine tasting in historic cellars dotted around the town and enjoy a traditional Tuscan lunch at a local trattoria. End your day with a scenic sunset walk along the city walls or a short drive to San Biagio church before dinner.
What is Montepulciano known for?
Montepulciano is most famous for Vino Nobile di Montepulciano, a prestigious red wine produced in the region. It’s also known for its well-preserved medieval and Renaissance buildings, gorgeous countryside views, artisan culture, and proximity to other Tuscan destinations like Pienza, Montalcino, and Siena. Its elevated position offers one of the best panoramic points in Tuscany.
Are there any unusual or lesser-known things to do in Montepulciano?
Yes! Explore Montepulciano’s underground city, a labyrinth of ancient Etruscan tunnels and wine cellars beneath the town. Visit lesser-known artisan workshops showcasing hand-painted ceramics or taste pecorino cheese from nearby Pienza. The Medici Fortress, recently restored, also hosts exhibitions and offers panoramic views with fewer crowds.
What are the best hotels in Montepulciano?
- La Locanda di San Francesco – A boutique hotel with panoramic views right in the heart of the city.
- Etruria Resort & Natural Spa – Offers luxurious rooms and an on-site spa for a relaxing stay.
- Palazzo Carletti – Elegant and centrally located, combining historic charm with modern comfort.
- Agriturismo La Corte del Cavalierino – Perfect for countryside stays just outside the main town, with vineyards and a pool.
What are the best restaurants in Montepulciano?
- Osteria Acquacheta – Known for its incredible bistecca alla fiorentina and rustic setting.
- La Porta di Bacco – Offers modern twists on traditional Tuscan dishes with an extensive wine list.
- Ristorante La Grotta – Located near San Biagio, perfect for a romantic meal with fine Tuscan cuisine.
- Trattoria di Cagnano – Affordable, local-style dining loved by both locals and tourists.
- Degusteria Ristorante – Ideal for wine pairings and refined regional dishes.
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