The Complete Guide to Montepulciano, Italy: Tuscany’s Hilltop Wine Town

We revisited Montepulciano during our Tuscan itinerary this past fall, and were reminded just how special this hilltop town is. Set in southern Tuscany on the edge of the Val d’Orcia, Montepulciano is best known for Vino Nobile wine and its underground cellars. After a second visit, this guide covers everything you need to plan your visit: the best things to see, eat, and do, from wine tastings and historic landmarks to my favorite restaurants and where to stay.

We stayed at Lupaia, a peaceful agriturismo just outside town with views of Montepulciano and its vineyards. Lupaia is the kind of place where you wake up and don’t want to leave, but we were excited to spend a day exploring the village.

Despite its small size, Montepulciano can easily fill a half-day. One of my favorite things to do is to simply walk the village’s main street, Il Corso. The street is lined with wine shops, artisan boutiques, and cafes, with views of the Val d’Orcia around every corner. Just outside the walls, the Tempio di San Biagio is one of the most beautiful Renaissance churches in Tuscany.

Of course, it wouldn’t be a trip to Montepulciano without trying the town’s famous red wine, Vino Nobile di Montepulciano. I recommend stopping in at a few wine bars and cellars along the way (many are hosted in underground cellars below the village). Montepulciano also pairs well with nearby Pienza, one of my favorite villages in Tuscany, and where you’ll find incredible pecorino cheese.

Read on for my full recommendations for how to make the most of your time in Montepulciano.

Short on Time? Here Are My Top Picks for the Best Hotels and Things to Do in Montepulciano:

Hotels

1. Lupaia ($$$$ / Where I Stayed), for a luxury boutique hideaway with incredible views and a standout restaurant
2. Casa Newton ($$$), for the best design-forward countryside stay with a modern, relaxed feel
3. Stelle di Monte ($$), for the best romantic Tuscan bed and breakfast

Airbnbs

1. Panoramic 2 Bedroom Apartment, for a quiet hilltop stay with free parking and a host who arranges wine tastings
2. Restored 2 Bedroom Oratory, for a unique two-story apartment with Val d’Orcia views
3. Cozy 1 Bedroom with Private Terrace, for a valley-view apartment in the historic center with free parking steps from restaurants and wineries

Things to Do

1. Tour Some of Montepulciano’s Best Wine Cellars, for a guided tasting through one of the town’s historic underground cellars
2. Take a Pasta and Tiramisu Making Class, for a hands-on cooking class in Montepulciano with a local chef

Travel Tips

1. Rent a Car to Explore Tuscany — The best way to experience Tuscany is by driving yourself. We book our rental cars in Europe through Discover Cars, choose full coverage insurance, and opt for trusted companies like Alamo, Hertz, or Sixt. Driving in Tuscany is straightforward, and having a car makes day trips from Siena much easier. Book your car with Discover Cars here.
2. Get Cell Data Before You Arrive — The easiest way to navigate Tuscany is with reliable cell data. We use Holafly unlimited data eSIMs for all international travel and recommend installing your eSIM before arrival so maps, ride-sharing, and directions work the moment you land. Pre-Purchase your Holafly eSIM here.

Helpful Guides to Plan Your Trip

If Montepulciano is part of a broader Tuscany route, start with my Tuscany itinerary for the overall trip structure, then use my guide on where to stay in Tuscany to choose the right base. From there, my guides to San Gimignano, Siena, and the Val d’Orcia (including Pienza and Montalcino) will help you plan countryside day trips, with route ideas, pacing, and where to stop for lunch or a winery visit.

For Florence, I have a 3-day Florence itinerary, a full Florence city guide covering the best things to do, and a guide on where to stay in Florence. And if Tuscany is part of a longer first trip to Italy, my 12-night first-timers Italy itinerary shows how it all fits into a broader Rome–Florence–countryside route. For more on where to go in Italy, start with my list of the best cities in Italy and 10-day Italy itinerary.

The Montepulciano, Italy Travel Guide

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What to Know Before You Visit Montepulciano

Is Montepulciano Worth Visiting?

Absolutely. Montepulciano is one of Tuscany’s most charming hilltop towns, with cobbled streets lined with small boutiques and artisan stores. The town is full of Renaissance and medieval architecture, and the views over the surrounding vineyards and rolling hills are incredible. Add in the town’s famous red wine, Vino Nobile di Montepulciano, and you have reason enough to build a half-day around a visit here.

Vino Nobile vs. Montepulciano Wine: What’s the Difference?

Vino Nobile di Montepulciano is the town’s signature red wine, made primarily from Sangiovese grapes (locally called Prugnolo Gentile). The name refers to the town, not the grape. Montepulciano d’Abruzzo is a completely different wine from a different region, made from the Montepulciano grape. The confusion is common, but the two couldn’t be more different.

How Much Time to Visit Montepulciano?

I’d recommend dedicating around half a day and a meal (either lunch or dinner) to enjoy Montepulciano. Around six hours gives you enough time to explore the key landmarks, enjoy a wine tasting at one of the cellars or wine bars, and soak up the village atmosphere. Montepulciano makes for a great half-day paired with nearby Pienza.

Getting Around Montepulciano

Montepulciano’s old town is compact and walkable, though very steep from the bottom. I recommend wearing comfortable shoes for exploring.

Travel Tip: Montepulciano has a tourist shuttle bus (called the City Tour Bus or Bus Navetta) that runs from the lower town up to the top. The shuttle is especially helpful if you’d rather skip the steep climb to the top. Be sure to check the latest schedules, as the service is seasonal.

Getting to Montepulciano from Florence

I recommend visiting Montepulciano by car; the journey from Florence takes about 1 hour and 30 minutes via the A1 and E35. I don’t recommend traveling from Florence by public transport, as the journey takes more than four hours.

Where to Park in Montepulciano

Driving is restricted within the city walls, so you have to park in one of the lots surrounding the center. We always try to park in Parcheggio Via Bernabei first. The lot is quite small, but close to the main village entrance. When that’s full, we park at Parcheggio Piazza Nenni N5, which is across the street and much larger. Parcheggio P8, Il Bersaglio is another option on the south end of town.

Timing and Weather in Montepulciano

My latest trip to Tuscany was in early fall, from late September to early October. I loved this time of year, as the weather is warm but not too hot, and the harvest season is in full swing. Spring (March through May) is also a great time to visit, with pleasant weather and fewer crowds. Summer is very hot and busiest with tourists. Winter has fewer crowds, but some wineries and attractions operate limited hours.

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Where to Stay in Montepulciano, Italy (and Nearby)

If you want to walk to dinner and aperitivo, stay inside Montepulciano’s historic center. If you’re after vineyard views and quiet, the countryside just outside town is the better base.

Best Hotels in Montepulciano (and Nearby)

1. Lupaia ($$$$ / Where I Stayed) — for a luxury boutique hideaway with only 12 rooms, incredible views, and a standout restaurant.
2. Casa Newton ($$$) — for a former countryside estate now turned boutique hotel, the mid-century styling and gorgeous gardens make for an idyllic stay between Montepulciano and Pienza.
3. Agriturismo Il Rigo ($$) — for an ancient stone farmhouse now offering agriturismo stays in the Val d’Orcia. With an organic farm on site and surrounded by the rolling hills, this is a truly authentic Tuscan getaway.
4. Stelle di Monte ($$) — for a romantic villa with exposed stone walls, garden views, and a terrace overlooking the surrounding countryside. The on-site restaurant is a nice bonus for evenings when you don’t feel like driving into town.

Best Airbnbs in Montepulciano

1. Panoramic 2 Bedroom Apartment, a quiet hilltop apartment with a terrace overlooking the hills, free parking, and a host who arranges wine tastings
2. Restored 2 Bedroom Oratory, a 17th-century oratory turned two-story apartment with Val d’Orcia views and a vinyl stereo in the living room
3. Cozy 1 Bedroom with Private Terrace, a historic center apartment with a large terrace, valley views, and free parking steps from restaurants and wineries

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The Best Things to Do in Montepulciano, Italy

Explore the Old Town and Il Corso

Montepulciano’s historic centro is compact and best explored on foot. The main street, Il Corso, runs through the middle of the hilltop town and is lined with wine shops, artisan boutiques, and cafes.

Heading to Piazza Grande, you’ll pass hidden courtyards, viewpoints over the Val d’Orcia, and lots of great places to stop for a glass of wine or something light to eat. Palazzo Comunale anchors the piazza with its 14th-century design and bell towers, alongside the Renaissance well designed by Antonio da Sangallo.

See the Tempio di San Biagio

While most of the attractions are located within the town walls, just outside is the Tempio di San Biagio. Considered one of the most beautiful Renaissance churches in Tuscany, the 16th-century church is surrounded by cypress trees and rolling countryside. The Greek cross design, by Antonio da Sangallo the Elder, draws from the same architectural tradition as some of Italy’s most famous churches. Even if you only have half a day in Montepulciano, San Biagio is a must-see.

Sample the Famous ‘Vino Nobile di Montepulciano’ at Local Wine Bars

Montepulciano is best known for its Vino Nobile di Montepulciano, one of Italy’s most prestigious red wines. Many of the town’s wine cellars sit beneath Renaissance-period palazzi, and you can taste a range of local wines underground.

Most wineries and cantinas require reservations, especially for guided tastings or cellar tours. Some of the most well-known cantinas in Montepulciano include:

• De’ Ricci Cantine Storiche, one of the most famous historic cellars in town
• Ercolani Cellars, extensive underground tunnels beneath Montepulciano
• Gattavecchi Winery, classic producer with a long history
• Vecchia Cantina di Montepulciano, one of the oldest cooperative wineries (5-minute drive from town)

If you don’t have a reservation, Talosa is a great option. I managed to walk in and enjoy a tasting without a booking, which made for an easy stop while exploring the town.

Visit More of Montepulciano’s Churches

Beyond San Biagio, Montepulciano has a few more churches worth stepping into as you explore.

• Sant’Agostino Church — Located along Montepulciano’s main street, Sant’Agostino is loved for its Renaissance stone facade designed by Michelozzo. Originally built in the 13th century, the church is an easy stop as you walk uphill through the old town.
• Church of Santa Maria Assunta (Montepulciano Cathedral) — On Piazza Grande, the cathedral has an understated exterior that gives way to notable religious artwork inside, including an altarpiece by Taddeo di Bartolo. Worth a stop while you’re in the piazza.
• Chiesa del Gesù — A quieter 16th-century church with a simple, symmetrical design reflecting the Jesuit architecture of the period. The church is a quick, easy visit if you’re nearby.

Unwind With a Glass of Wine at Sax Wine Bar

I recommend stopping by Sax Wine Bar if you’d like to relax with a drink. The bar is a chic spot to enjoy a glass of Vino Nobile or Brunello di Montalcino in a casual setting, without committing to a formal tasting. Great for winding down after sightseeing or before heading to dinner.

Explore the Nearby Town of Pienza

Pairing Montepulciano with nearby Pienza makes for a perfect southern Tuscan day trip. A short 20-minute drive from Montepulciano, Pienza is a UNESCO-listed village known for its architecture, scenic viewpoints, and world-famous pecorino cheese.

The historic center was redesigned in the 15th century by Pope Pius II as an “ideal city.” While there, go for a stroll through Piazza Pio II, admire the architecture, and visit the Palazzo Piccolomini. Don’t miss my full guide to Pienza for more on where to eat and what to see.

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The Best Montepulciano Restaurants

Osteria del Borgo

We enjoyed lunch at Osteria del Borgo right on Piazza Grande. The terrace overlooking the Val d’Orcia is hard to beat, and the food was excellent: handmade pasta and local meats like Chianina beef. The building dates back to the 1270s. If you’re visiting during the busier seasons, make a reservation, especially to secure a terrace table.

Osteria Acquacheta

Osteria Acquacheta is one of the most popular restaurants in Montepulciano, and for good reason. The Florentine steak and grilled meats are the stars here, and the atmosphere is casual with shared tables and rustic interiors. Reservations are essential.

Osteria del Conte Montepulciano

Tucked away near the fortress and San Biagio area, Osteria del Conte is a classic trattoria with cozy interiors and traditional Tuscan cooking. The menu focuses on regional dishes and local wines. Make a reservation if you can.

Il Casale Agricampegio

I absolutely recommend having lunch at this organic agriturismo farmhouse restaurant. Just a short drive outside Montepulciano, Il Casale is perfect for a leisurely lunch in a classic Tuscan countryside setting. The menu is built around fresh produce, local cheeses, and excellent wine. The panoramic views and relaxed atmosphere made this one of our favorite meals in the area.

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