The Best Things to Do in Tuscany’s Wine Capital – From Wine to Views
If you’ve ever dreamt of wandering through sun-dappled streets, sipping world-class wine, and stepping back in time to a place where history lingers in every cobblestone, then Montepulciano is calling your name. Nestled between two valleys (Val d’Orcia and Val di Chiana) in the heart of Tuscany, this medieval hilltop town is not just a destination—it’s an invitation to experience Italy in its most authentic, breathtaking form.
I visited Montepulciano on my recent road trip and here’s my guide to the best things to do in Montepulciano, the wine capital of Tuscany.
Let me take you on a journey through Montepulciano, and I promise, you’ll want to book a ticket the moment you finish reading.
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From Wine to Views: 11 Best Things to Do in Montepulciano
1. Stroll Through the Timeless Streets of the Old Town
First things first: Montepulciano’s old town is like something out of a dream. Picture this: narrow streets lined with centuries-old stone buildings, their facades bathed in warm, golden light, with the scent of fresh bread and rich coffee wafting through the air. As you meander through the heart of the town, it’s impossible not to feel as though you’ve stepped into a living painting.
Start your journey at the majestic Porta al Prato, one of the main entrances to Montepulciano. From here, stroll along Il Corso, the town’s main street, where you’ll find a delightful mix of charming boutiques, local shops, and cozy cafes.
The street will lead you straight to the heart of Montepulciano—Piazza Grande, the central square. There you’ll be greeted by the Cattedrale di Santa Maria Assunta (Cathedral of Saint Mary of the Assumption), and the majestic Palazzo Comunale (Town Hall).
Take your time wandering through Montepulciano’s winding alleyways and charming shops. You’ll find artisan boutiques offering local crafts, leather goods, and handmade jewelry that reflect the town’s rich heritage.
I loved simply getting lost in the labyrinth of streets, with no set destination in mind, letting the town’s beauty unfold at its own pace. There’s a timelessness here that feels both comforting and exhilarating.
2. Discover the Torre di Pulcinella in Piazza Michelozzo
While Montepulciano’s main square, Piazza Grande, often steals the spotlight, there’s another delightful gem waiting for you in Piazza Michelozzo. It’s here that you’ll find the Torre di Pulcinella, a charming clock tower that adds a dash of whimsy to the town’s architectural lineup.
This quirky tower is a reminder that there’s more to Montepulciano than just breathtaking views and Renaissance beauty—it also has a playful side! Standing in the heart of the square, the Torre di Pulcinella is adorned with a sculpture of Pulcinella, the iconic figure of the Italian commedia dell’arte. The clock tower itself is beautifully designed, and the cheerful figure of Pulcinella adds an extra touch of character, making it a fun and unique photo opportunity.
When I visited, I was struck by how the tower blends effortlessly into its surroundings, while still offering something unexpected and delightful. It’s one of those sights that brings a smile to your face. Don’t rush past it—take a moment to appreciate the lighthearted beauty of this little piece of Montepulciano’s charm.
3. Check Out the Well of Griffins and Lions (Il Pozzo dei Grifi e dei Leoni)
Tucked in the corner of Piazza Grande, the Well of Griffins and Lions (Il Pozzo dei Grifi e dei Leoni) is an architectural marvel—and a perfect example of the town’s rich heritage.
As you approach the well, the magnificent carvings of griffins and lions—symbols of power and protection—capture your attention. They’re beautifully preserved, and the intricate detail in the stonework speaks volumes about the craftsmanship of centuries past.
I couldn’t help but marvel at how the well, though centuries old, still stands as a testament to the town’s long and storied history. The beauty of the well, combined with its rich symbolism, is something I won’t soon forget.
4. Climb the Clock Tower for a View Like No Other
One of the most unforgettable experiences in Montepulciano is climbing the Clock Tower on the Palazzo Comunale. Climb 150 steps to the top. Trust me, it’s worth every step. As you make your way up the narrow staircase, you’ll feel like you’re uncovering a piece of history. The tower has stood for centuries, and as you ascend, you can almost imagine the generations of townspeople who’ve looked out over the same incredible view.
When you finally reach the top, the panorama that unfolds before you is nothing short of magical. From up here, you can see Montepulciano’s terracotta rooftops spilling down the hill, vineyards stretching out across the valleys, and distant Tuscan hills that seem to go on forever. It’s a 360-degree view that captures the essence of this beautiful corner of Italy.
I remember the sense of awe I felt standing there, the wind in my hair, taking it all in. It’s one of those moments that makes you stop and appreciate just how beautiful the world is. It’s an experience that I think will stay with you long after you leave.
5. Indulge in the Wine That Made Montepulciano Famous
Tuscany is synonymous with wine, but Montepulciano stands out for its Vino Nobile di Montepulciano, a rich, complex red wine that’s been produced here for centuries. If you’re a wine lover—or even if you’re not—this is an experience you can’t miss.
Many of the town’s charming wineries offer tastings, often in caves carved into the hillsides. These cellars have an air of mystery and tradition, and the wine itself? Simply sublime. I still remember my first sip of Vino Nobile—it was like tasting the very essence of the Tuscan landscape.
If you want to get hands-on, book a tour at one of the family-owned wineries. I highly recommend booking a tour with a guide who can walk you through the wine-making process and share stories of the land that makes this wine so exceptional. And trust me—by the end of your tasting, you’ll be dreaming of the next glass!
Many wineries offer tours and tastings, where you can sip on wine as you learn about the art of winemaking.
- De’Ricci Cantine Storiche: Visit this historic winery for a deep dive into Montepulciano’s winemaking heritage. It’s housed in an ancient underground cellar. They have guided tours with wine tastings, which you need to book in advance.
- Cantina Contucci: One of the oldest wineries in the area, it’s a must for anyone serious about Tuscany’s wine scene. You can tour its wine cellar by yourself for free without wine tasting.
- Cantina Ercolani: This family-owned winery is a great place to taste the fine Vino Nobile and take in the picturesque Tuscan countryside. They have free guided tours with wine tastings.
6. Admire the Garden of the Fortezza Medicea
For a view that will make your heart skip a beat, head up to the Fortezza Medicea (Medici Fortress). This 16th-century fortress, once built for defense, now offers the loveliest garden in Montepulciano. The sheer beauty of the place will leave you in awe. It’s the perfect spot to pause, take a deep breath, and soak in the serenity of the garden.
Inside the fortress is Enoliteca Consorzio Vino Nobile. Sample Vino Nobile di Montepulciano, Rosso di Montepulciano, and Vin Santo di Montepulciano wines in the shop’s garden with inspiring views of the Tuscan countryside.
7. Treat Yourself to a Meal You Won’t Forget
Now, no trip to Tuscany would be complete without indulging in the local cuisine. Montepulciano, with its rustic charm, is full of inviting trattorias and restaurants that serve up some of the region’s finest dishes.
Start with a plate of pici—a thick, handmade pasta typically served with a hearty meat ragu. Paired with a glass of local wine? Heaven. I found myself savoring every bite as if the flavors of Tuscany itself were dancing on my tongue. You can’t go wrong with a bowl of ribollita (a rich Tuscan vegetable soup) or a slice of pecorino cheese, a local specialty.
Don’t forget dessert! The cantucci (almond biscuits) dipped in Vin Santo (a sweet dessert wine) is the perfect way to end your meal on a sweet note.
- Osteria Acquacheta: For a truly authentic Tuscan meal, this rustic eatery serves up melt-in-your-mouth steaks and hearty pasta dishes in a cozy atmosphere.
- La Porta: Located in Monticchiello, 15 minutes from Montepulciano, this restaurant offers fantastic food with an incredible view of the Val d’Orcia.
8. Sample Pastries and Sip Coffee at Caffé Poliziano
Now, I have a confession: I’m a sucker for a great coffee shop. And Caffé Poliziano in the heart of Montepulciano is the kind of place that makes you feel like you’ve found a little slice of heaven.
Picture this: you’re sitting at a table with a yummy cake and a warm cup of coffee in hand in the elegant Art Nouveau interior of Caffé Poliziano in Montepulciano. The world seems to slow down as you sip your coffee and eat your cake, while the sounds of the town gently fade into the background.
I could’ve spent hours here, just savoring the moment. It’s one of those simple pleasures that make travel so special. The charm of Caffé Poliziano isn’t just in the coffee or cakes/pastries (although both are exceptional); it’s the atmosphere that makes it feel like an essential part of the Montepulciano experience. It’s a perfect spot to recharge, take a breath, and enjoy the slower pace of life that defines Tuscany.
Caffé Poliziano has also outside seating on a balcony that overlooks the Valdichiana (Val di Chiana). The views are something you won’t easily forget! Many distinguished guests, like Giosuè Carducci, Pirandello, Giulietta Masina, Ornella Muti, and Federico Fellini enjoyed Caffé Poliziano in Montepulciano. Be sure to check out this historic cafe in Montepulciano!
9. Uncover the Town’s Cinematic Connection
Fans of movies will appreciate the fact that Montepulciano has been a backdrop for a number of films, most notably New Moon (part of the Twilight series). Even if you’re not a fan of the franchise, it’s fun to wander through the spots featured in the movie, like the charming Piazza Grande or the historic Palazzo Comunale. It’s a quirky way to engage with the town’s more modern history while soaking in its ancient charm. You can read more about the Twilight Saga New Moon tour in Montepulciano here.
10. Inspect the Views of the Tuscan Countryside from Veduta Panoramica at Sunset
When the day begins to fade and the golden light softens the landscape, head over to Veduta Panoramica (the panoramic viewpoint). Situated just a few steps from Piazza Grande, this spot offers a sweeping view of the Tuscan countryside that’s nothing short of mesmerizing.
I’ll never forget the views I saw from there. I wondered what the views look like at sunset. So, I returned to Veduta Panoramica at sunset! The sun dipped behind the distant hills, casting a warm, amber glow across the vineyards and olive groves. The colors were so vibrant and vivid, it almost felt like I was looking at a painting come to life. It’s a moment that stops you in your tracks and reminds you of just how stunning this part of the world truly is. On my first visit, I took some photos. But on my sunset visit, I decided to savor the moments without taking photos!
The air cools as the evening settles in, and if you’re lucky, you might catch the last traces of sunlight glinting off the Tuscan countryside framed by the undulating hills. It’s one of those simple, yet profound experiences that will stay with you long after you leave. Whether you’re alone, with a partner, or with friends, the beauty of this moment is something everyone should experience.
11. Step Back in Time at the Church of San Biagio
One of Montepulciano’s most serene and stunning gems is the Church of San Biagio. This Renaissance masterpiece sits just outside the town center, set against the rolling Tuscan hills. It’s one of those places that’s easy to overlook if you’re rushing through Montepulciano but trust me, it’s worth the detour.
The church’s delicate marble facade, paired with its tranquil surroundings, makes it feel like a secret retreat for the soul. Inside, the simple yet elegant design invites a quiet sense of reflection, and the view from the church’s grounds is absolutely breathtaking. Spend some time here, take a few photos, or simply sit and enjoy the peaceful atmosphere. Visiting the church is well worth the small entrance fee.
12. Embrace the Quiet Beauty of Montepulciano’s Surroundings
While Montepulciano itself is a treasure trove of experiences, the surrounding countryside offers its own brand of magic. Whether it’s a leisurely walk through the vineyards or a scenic drive through the Tuscan hills, the beauty of the area will capture your heart.
For a truly special experience, sit in the car and explore the scenic roads that wind around the town. The landscape is breathtaking, and there’s something incredibly peaceful about being immersed in the rolling hills and the tranquility of nature.
How to Get to Montepulciano
Has my guide to the best things to do in Montepulciano made you wish to visit Montepulciano? I hope it has! Wondering where Montepulciano is?
Montepulciano is located in the heart of Tuscany, making it a great stop on any road trip. It’s about:
- 1.5 hours from Florence
- 45 minutes from Siena
- 2 hours from Rome
- 50 minutes from Arezzo
- 40 minutes from Cortona
- 20 minutes from Pienza
- 45 minutes from Montalciano
The nearest airports are Florence Airport (about 1.5 hours away) and Rome’s Fiumicino Airport (about 2 hours away). From there, you can rent a car and enjoy the scenic drive through Tuscany’s rolling hills and picturesque towns. Driving through the Val di Chiana from Cortona to Montepulciano and through the Val d’Orcia toward Pienza is particularly breathtaking, with views that feel straight out of a painting.
You can visit Montepulciano on this amazing day tour from Florence, this day tour from Siena, and this highly popular day tour from Rome.
Where to Stay in Montepulciano
Montepulciano offers a variety of places to stay that cater to different tastes and budgets. From luxurious vineyards to cozy boutique hotels, there’s something for every traveler. Here are some great options to consider:
Luxury: Villa Cicolina– Set in a stunning 17th-century villa surrounded by olive groves and vineyards, Villa Cicolina offers luxurious rooms with a rustic charm. It’s perfect for those looking for a peaceful and elegant escape, along with a pool and panoramic views of the Tuscan countryside.
Mid-range: Albergo Il Marzocco– Located just outside the main square, this family-run hotel offers traditional Tuscan hospitality in a cozy setting. It’s known for its warm, friendly service and ideal location for exploring Montepulciano’s sights and nearby wineries
Best Time to Visit Montepulciano
The best time for a road trip through Tuscany—and especially to Montepulciano—is during the spring and fall. The temperatures are mild and the crowds are fewer than in summer. I visited Montepulciano in May when the countryside was lush and green. I can not recommend enough visiting Tuscany in May. Late September and October are also magical, as the vineyards begin to change color and the wine harvest is in full swing.
Conclusion
If you’re looking for a destination that offers history, beauty, charm, and world-class wine, Montepulciano is waiting for you. From its medieval streets to its stunning viewpoints, this Tuscan town is the kind of place that lingers in your memory long after you leave. So, pack your bags, rent a car, and set off on a road trip to Montepulciano. You’ll be glad you did.
Check out affordable rental cars at Rome Fiumicino Airport, and great rental car deals at Florence Airport.
Hope you like my guide to the best things to do in Montepulciano, Italy! Have you been to Montepulciano, or is it on your bucket list? I’d love to hear your thoughts and experiences in the comments below!
- Savoring Montepulciano: Best Things to Do in Tuscany’s Wine Capital – From Wine to Views - January 14, 2025
- Pienza Travel Guide: A Pearl of Val d’Orcia, Tuscany - January 11, 2025
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