Spending One Day in Montepulciano, Italy: Best Things to Do

Here’s how to spend the perfect day in Montepulciano, Italy—wine, views, and pasta included.

Perched high in the hills of southern Tuscany, Montepulciano is a town that seems tailor-made for postcards—and wine labels. With its Renaissance architecture, panoramic views, and deep roots in winemaking, it offers a perfect blend of culture, scenery, and gastronomy without the overwhelming crowds of some of Tuscany’s more trodden spots.

This Montepulciano travel guide covers everything you need to know for a well-paced visit—what to see, where to eat, how to get there, and, most importantly, where to taste the town’s famed Vino Nobile di Montepulciano.

You don’t need a full weekend here; ideally, set aside half a day to one full day to explore the town at a relaxed pace. It’s compact enough to walk end-to-end in an afternoon, yet rich enough in wine cellars, scenic terraces, and tucked-away trattorias to fill several unforgettable hours.

That said, when I visited Montepulciano Italy in the off-season—early spring, with the stone streets slick from the morning rain and barely another tourist in sight—I stayed for two full days, and I was glad I did. The slower pace gave me time to soak it all in: long, quiet lunches, wine tastings with the winemakers themselves, and uninterrupted views of the Val di Chiana wrapped in a soft winter mist.

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How to Get to Montepulciano, Italy

Getting to Montepulciano requires a bit of effort, given its sublime hilltop location, but it’s well worth the trip. I’d highly recommend driving to Montepulciano (just not in peak season) and combining the village with other nearby Tuscan villages as part of a great Tuscan or Italian road trip.

By Car: If you want full freedom to stop for sunflower fields, crumbling stone farmhouses, and impromptu pecorino tastings (which, of course, you do), rent a car. From Florence, Montepulciano is about a 1.5–2 hour drive south along the A1 Autostrada. From Rome, it’s around 2 hours heading north. The last leg winds through the Val di Chiana and is pure Italian countryside poetry.

Just note: parking inside the historic center is limited, so plan to park in one of the lots just outside the walls and hoof it uphill—preferably with gelato in hand.

By Train: There’s no direct train to Montepulciano’s historic center. The nearest station is Montepulciano Stazione, about 12 km away, which confusingly serves the modern outskirts and not the hilltop town itself.

You’re better off taking a train to Chiusi-Chianciano Terme, a larger and better-connected hub about 30 minutes from Montepulciano by car. From Florence or Rome, regional trains to Chiusi run frequently and make for a scenic, sleepy ride through the Tuscan countryside.

Once in Chiusi, grab a taxi or pre-arranged transfer—public buses exist, but their schedules are a bit… whimsical.

By Bus: While slower and less flexible, buses do reach Montepulciano from nearby towns like Siena and Pienza, as well as from Chiusi. This can be a scenic, budget-friendly option for those without a car. Be sure to double-check schedules, as routes are often reduced on weekends and holidays. And bring a book—these are the “stop everywhere” kind of buses.

By Tour or Private Transfer: If you’re looking to sip and not steer, consider a day trip or overnight tour from Florence, Siena, or even Rome. Many wine-focused tours include Montepulciano on their itineraries, along with a few well-lubricated stops at nearby vineyards.

Private transfers are also an option, albeit a pricier one, perfect for honeymooners, celebrants, or anyone who believes vacation should not include deciphering Italian bus timetables.

Best Time to Visit

The best time to visit Montepulciano, Italy is during the shoulder seasons—spring (April to June) and fall (September to October)—when the weather is mild, the countryside is at its most photogenic, and the town isn’t overwhelmed with tourists.

Fall is especially ideal for wine lovers, as harvest season brings vibrant colors to the vineyards and plenty of opportunities for tasting Montepulciano’s famed Vino Nobile straight from the source.

Spring offers lush landscapes, blooming wildflowers, and a peaceful atmosphere perfect for exploring the town’s winding alleys and panoramic viewpoints. As someone who lives in Italy, I can say that spring is my favorite season – the landscapes look gorgeous.

Summer (July and August) can be hot and crowded, though lively, with festivals and long, sun-soaked days; winter, while quiet and cold, has its charm for those seeking solitude and lower prices, but note that many businesses in a town as small as Montepulciano will close for the season.

Best Things to Do in Montepulciano, Italy

Stroll the Town’s Streets

Montepulciano Italy, is best explored on foot—this is a town made for slow wandering, spontaneous detours, and frequent gelato stops.

The main drag, Il Corso, slices through the historic center like a Renaissance catwalk, leading you from the city gates all the way up to the grand Piazza Grande at the top. It’s the town’s spine, lined with elegant palazzi, boutique wine shops, leather artisans, and cafés that seem to exist solely for sipping espresso while watching life amble by.

But the real charm lies in veering off-course. Lose yourself in the labyrinth of side streets—steep, cobbled, and often ending in breathtaking valley views or tiny chapels that feel like age-old secrets. Each corner delivers a postcard-perfect vignette: laundry fluttering from stone balconies, a nonna tending geraniums in terracotta pots, the echo of your footsteps on ancient stones.

Visit Piazza Grande and the Palazzo Comunale

At the very heart of Montepulciano—both geographically and atmospherically—is Piazza Grande, a striking square that feels like a film set (and in fact, it has been—Twilight: New Moon, anyone?).

Surrounded by Renaissance architecture and perched dramatically at the town’s highest point, this piazza is the place to soak in Montepulciano’s grandeur. The standout building is the Palazzo Comunale, Montepulciano’s medieval town hall, with its unmistakable Florentine flair—think Palazzo Vecchio’s little cousin, right down to the crenellated clock tower.

And yes, you can climb it. The ascent is narrow and mildly vertigo-inducing, but the panoramic reward at the top is worth the semi-sweat: a 360-degree sweep of vineyards, tiled rooftops, and undulating hills that look too perfect to be real. It’s one of the best views in the region.

Visit some Wineries in Montepulciano

You can’t come to Montepulciano, Italy, and not drink the wine—it would be like going to Naples and skipping the pizza.

Montepulciano is home to Vino Nobile di Montepulciano, a DOCG red wine that’s been produced here for centuries, long before wine tourism became the polished industry it is today. Many of the town’s historic palazzi double as wine cellars—yes, right in the center of town—making it incredibly easy to taste as you go.

One of the most established stops is Cantina Contucci, a working winery housed inside a 16th-century palazzo with vaulted underground cellars. Just a few steps away, Cantina De’ Ricci offers a dramatic setting and guided tastings beneath its historic stone arches.

Talosa is another standout, combining a central location with a sleek tasting room and impressive cellar tours. Most tastings include a range of local labels, from Vino Nobile and Rosso di Montepulciano to the occasional Super Tuscan, and can often be done without a reservation.

If you’re interested in going deeper—learning about aging processes, local grape varieties, or doing a vertical tasting—it’s worth booking in advance. Whether you’re a seasoned oenophile or just want to sample a few glasses with some cured meats and cheese, Montepulciano makes it easy to enjoy the region’s wine culture without ever leaving town.

Embark on the Montepulciano Wine Route

This and the above go hand in hand, but if you want to go beyond Montepulciano’s town cellars and actually see where the wine is grown, the Strada del Vino Nobile di Montepulciano—the Montepulciano Wine Route—is the next step.

Winding through the Tuscan countryside just beyond the city walls, this route links many of the region’s top wine estates and offers a front-row seat to the landscapes that define the area’s winemaking identity: cypress-lined drives, undulating vineyards, and historic estates tucked into the hills.

It’s a scenic, immersive experience, and while you can self-drive, it’s far better to join a wine tour or hire a private driver so you can do as many wine tastings in Montepulciano as you like without having to worry about driving.

Wineries along the route range from polished operations to small, family-run spots. Avignonesi is one of the most popular, known for its organic and biodynamic wines, sweeping views, and full-on vineyard lunches.

Boscarelli is a more intimate, old-school option with cult-like status among serious wine lovers. Then there’s Salcheto, a sustainability-forward estate with a modern tasting room and an on-site restaurant—a great place for lunch between pours.

Many Montepulciano wineries require reservations, especially during harvest season, and most offer guided tastings that include Vino Nobile, Rosso di Montepulciano, and often a few special cuvées.

A tour takes the pressure off logistics and lets you dive deeper into the winemaking process, often with added perks like behind-the-scenes cellar access or curated food pairings. Some of the best wine tours I recommend in the area are below:

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Take in the View from the Panoramic Terrace

One of the simplest but most rewarding things to do in Montepulciano is to head to one of its panoramic terraces and take in the view. The most popular spot is right near Piazza Grande, where a stone lookout offers clear, unobstructed views across the Tuscan countryside.

From here, you can see vineyards, olive groves, and nearby hill towns stretching all the way to Lake Trasimeno on a clear day. It’s a great place to pause between sightseeing stops, take a few photos, or just get your bearings.

You’ll also find other panoramic points around the edges of the historic center—some well-marked, others tucked between quiet side streets. Visit in the early morning or late afternoon for softer light and fewer people.

Visit the Temple of San Biagio (Chiesa di San Biagio)

Just outside Montepulciano’s city walls, set against a backdrop of vineyards and open countryside, the Temple of San Biagio is one of the town’s most striking landmarks—and worth the short walk downhill to see it up close.

Built in the early 16th century, this freestanding Renaissance church is a textbook example of symmetry and proportion, designed by Antonio da Sangallo the Elder in a perfect Greek cross layout. The creamy travertine stone seems to glow in the sunlight, and the setting—completely detached from the rest of the town—adds to its quiet impact.

Inside, it’s simple and uncluttered, with a focus on clean lines and soft light, quite different from the ornate interiors typical of Italian churches. The walk back uphill into town can be a bit of a climb, but it’s nothing a glass of wine can’t fix afterward.

Visit the Civic Museum

For a deeper look at Montepulciano’s history beyond wine and Renaissance architecture, head to the Museo Civico Pinacoteca Crociani, the town’s Civic Museum. Tucked inside the 14th-century Palazzo Neri Orselli along the main street, the museum is compact but well-curated, showcasing a collection that spans Etruscan artifacts, medieval religious art, and Renaissance paintings.

It’s a quiet, worthwhile stop—especially on hot afternoons when a little air-conditioned culture goes a long way. And if you’re in the mood for something a bit more… unconventional, there’s also a Torture Museum in town, if that sounds more up your alley.

Where to Eat in Montepulciano, Italy

Montepulciano may be small, but it punches way above its weight when it comes to food. Here are a few standout spots to plan your meals around:

Osteria Acquacheta – A cult favorite for carnivores, especially famous for its bistecca alla fiorentina, served with zero frills and all the flavor. Reservations are a must—call ahead at least a few days in advance, or you’ll likely be out of luck.

La Vineria di Montepulciano – A perfect lunch stop with casual charm and standout flavors. Their charcuterie boards, local wines, and pasta dishes are fantastic—simple, seasonal, and beautifully done. We visited in winter and still loved the warm, welcoming vibe.

Le Logge del Vignola – For something more elevated, this Michelin-recommended spot delivers refined Tuscan cuisine in an intimate, atmospheric setting. Ideal for a special dinner with thoughtful plating and a killer wine list.

Ristorante degli Archi – A classic, cozy trattoria just outside the town walls that serves hearty, traditional fare. Great for homemade pasta, local meats, and warm hospitality without the fuss.

L’Altro Cantuccio Ristorante – A more upscale, creative option with a rustic-chic interior. Expect elevated Tuscan flavors with a modern twist, making it a great choice for foodies looking for something beyond the usual.

Where to Stay

Montepulciano is best visited for a day from elsewhere, as it doesn’t have that many luxury or boutique accommodation options. However, if you’re looking to stay overnight, there are a few standout places that offer a blend of comfort, charm, and Tuscan hospitality.​

Borgo San Vincenzo – Nestled amidst Montepulciano’s vineyards, this boutique hotel offers 21 uniquely designed rooms and suites, combining traditional Tuscan aesthetics with modern amenities. Guests can enjoy curated experiences and explore the surrounding wine country.

Villa Cicolina – A restored 16th-century villa that exudes rustic elegance. With panoramic views, terraced gardens, and an inviting pool, it’s a tranquil retreat just outside the town center.

Precise Tale Poggio Alla Sala – Located a short drive from Montepulciano, this luxury resort boasts beautifully appointed rooms, multiple pools, a spa, and an on-site restaurant, all set within a historic estate. ​

Palazzo Carletti – Situated in the heart of Montepulciano, this boutique hotel offers spacious rooms adorned with original frescoes, combining historical charm with modern comforts.

Villa Poggiano – Set in expansive parkland, this elegant villa features 14 rooms and suites, a classic Tuscan pool, and offers activities like cooking classes and wine tastings.

Top Tours to Visit Montepulciano, Italy

Whether you’re planning a day trip from Florence or Siena, or want a deeper dive into Montepulciano’s wine scene, joining a guided tour can take the guesswork out of logistics—and let you focus on what really matters: food, wine, and views.

Many tours include stops at top wineries, vineyard lunches, and time to explore the hilltop town itself. Here are a few tours to look out for:

Top Tips for Visiting

Montepulciano is incredibly rewarding to visit, but like many historic hill towns in Italy, it helps to go in prepared. Here are a few practical tips to make your visit smoother:

Parking: The historic center is mostly closed to non-resident traffic (ZTL), so if you’re driving, you’ll need to park outside the city walls. There are several paid lots, with Parcheggio P8 and P6 being good options for proximity. From there, it’s a bit of an uphill walk—wear comfortable shoes and pack light.

Wear Proper Footwear: Montepulciano is all cobblestones and slopes. Leave the flimsy sandals behind and opt for something with grip—you’ll thank yourself on the descents.

Book Wine Tastings in Advance: While a few wine cellars in town allow for walk-ins, most of the surrounding vineyards require reservations, especially during peak season. If you have a few must-visit in mind, lock them in ahead of time.

Plan for the Siesta Window: Like many Italian towns, Montepulciano slows down in the early afternoon. Some shops and restaurants close between 2 and 5 PM, so plan accordingly—either book a long lunch or use that window for panoramic views or a slow-paced stroll.

Stay Hydrated (and Not Just on Wine): Especially in the summer, the sun plus all that walking can be draining. Bring a water bottle—you’ll find plenty of fountains around to refill.

Use Montepulciano as a Base—or Not: If you’re set on a deep dive into the wine country, Montepulciano can make a great base for a night or two. But for those short on time or craving inner city luxury accommodations, consider visiting on a day trip from Siena, Florence, or a countryside villa nearby.

Timing is Everything: Try to arrive early in the day to beat the tour bus crowds, especially in summer. Golden hour is also spectacular here—perfect for photos, a glass of wine, and a slow descent back to your car.

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Ready for your trip to Montepulciano, Italy? Let me know your questions and comments below, and how you got on with these best things to do in Montepulciano, I’d love to hear from you.

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