Once you are inside the city walls, walking is the primary way to explore.

The Incline: Expect a serious workout. If you prefer to walk downhill, take the Pollicino to the top and meander your way back down.

The Corso: This is the main winding street that leads from the lower gate (Porta al Prato) up to the summit. It is lined with wine cellars, leather shops, and cafes.

The main bus terminal (Autostazione) is in Piazzale Pietro Nenni. Frequent buses connect to Pienza, Siena, and the Chiusi-Chianciano Terme train station.

Do not get off at “Montepulciano Stazione”—it’s 8km away and has very few connections. Instead, use Chiusi-Chianciano Terme and take a 30-minute bus or taxi from there.

Taxis don’t cruise the streets; you must call one or find them at the designated ranks near the bus station or the train station in Chiusi.

Montepulciano is a medieval and Renaissance hill town in southern Tuscany, Italy, and is most famous for its Vino Nobile di Montepulciano wine and its stunning architecture.

It is often called the “Pearl of the 16th Century” because of the high concentration of elegant Renaissance palaces and churches throughout the town.

1. The Wine (and the Confusion)

The town is synonymous with Vino Nobile di Montepulciano, one of Italy’s most prestigious red wines.

The Grape: It is made primarily from Sangiovese (known locally as Prugnolo Gentile).

The Mix-up: Don’t confuse it with Montepulciano d’Abruzzo. The latter is a wine from the Abruzzo region made from the Montepulciano grape; Vino Nobile is a wine from the town of Montepulciano made from the Sangiovese grape.

Underground Cellars: Many of the town’s historic palaces have “underground cities”—massive, vaulted wine cellars carved into the tufa rock where wine ages in giant oak barrels.

2. Landmark Architecture

Piazza Grande: The highest point in town and its social heart. It is surrounded by the unfinished Duomo (Cathedral) and the Palazzo Comunale, which bears a striking resemblance to the Palazzo Vecchio in Florence.

San Biagio (Tempio di San Biagio): A masterpiece of High Renaissance architecture located just outside the city walls. It’s a perfectly symmetrical, pale travertine church set against the rolling green hills.

Torre del Pulcinella: A clock tower featuring a mechanical statue of the classic Italian character Pulcinella, who strikes the bell on the hour.

3. Pop Culture & Events

The Twilight Saga: Fans of the Twilight series recognize the Piazza Grande as the filming location for Volterra in the movie New Moon.

Bravìo delle Botti: Every August, the town’s eight districts compete in a grueling race where pairs of “pushers” roll massive, 80kg (176lb) wine barrels uphill through the narrow, winding streets to the Piazza Grande.

4. Local Flavors

Beyond wine, the area is a culinary powerhouse known for:

Pici Pasta: A thick, hand-rolled spaghetti typically served with aglione (a local garlic sauce) or wild boar ragù.Pecorino di Pienza: Nearby Pienza provides some of the best sheep’s milk cheese in Italy, often aged in walnut leaves or grape must.

Montepulciano is best explored on foot, starting from the lower gate and winding your way up to the summit. Here are the must-visit spots:

1. Piazza Grande: The Civic Heart

This is the town’s main square and its highest point. It is surrounded by some of the most impressive Renaissance architecture in Italy:

Palazzo Comunale (Town Hall): Designed to look like the Palazzo Vecchio in Florence. You can climb the clock tower for the best 360-degree view of the Val d’Orcia and Val di Chiana.

The Duomo (Cathedral): A 16th-century cathedral known for its rough, unfinished brick facade, which gives it a uniquely rugged look. Inside, look for the Triptych of the Assumption by Taddeo di Bartolo.

Pozzo dei Grifi e dei Leoni: An elegant Renaissance well decorated with the Medici coat of arms and two lions.

2. The “Underground City” (Historic Wine Cellars)

Montepulciano is famous for the massive wine cellars carved directly into the tufa rock beneath its palaces. Many are free to enter for a self-guided walk:

Cantina De’ Ricci: Often called the “Cathedral of Wine” due to its massive stone arches and solemn, temple-like atmosphere.

Cantina Contucci: Located right on Piazza Grande, this cellar has been run by the same family for over 40 generations.

Cantina Ercolani: Features a fascinating “Underground City” where you can see ancient Etruscan tombs and secret passages alongside aging barrels.

3. Tempio di San Biagio

Located just outside the city walls at the end of a scenic cypress-lined path, this church is a masterpiece of High Renaissance design. Built entirely of pale gold travertine, its perfectly symmetrical Greek cross plan makes it one of the most photographed buildings in Tuscany.

4. Fortezza Medicea (Medici Fortress)

At the very top of the town, this 14th-century fortress has been beautifully restored. It now houses the Enoliteca Consorzio Vino Nobile, a modern wine shop where you can sample dozens of local wines using a “wine card” system while looking through glass floors at ancient archaeological ruins.

5. Notable Landmarks & Streets

Il Corso: The main “spine” of the town. This long, uphill street is lined with artisan workshops, leather boutiques, and gourmet food shops selling local Pecorino and honey.

Torre del Pulcinella: A medieval tower topped by a strange mechanical figure of Pulcinella (a classic Neapolitan character) who strikes the hours on a bell.

Porta al Prato: The majestic 14th-century main gate that serves as the entry point for most visitors starting their walk uphill.

6. Nature & Relaxation

Riserva Naturale Lago di Montepulciano: A peaceful lake reserve a few miles away, perfect for birdwatching or a quiet walk after a morning of sightseeing.

Terme di Montepulciano: If you need a break from the hills, these thermal baths in the nearby hamlet of Sant’Albino offer sulfurous spa treatments.

The “best” time to visit Montepulciano depends on whether you’re chasing the harvest energy, avoiding the crowds, or looking for that classic Tuscan glow.

Here is a breakdown of the seasons for 2026:

1. The Sweet Spot: Spring & Early Autumn

Months: May, June, September, and October.

Why: These are the most pleasant months for walking the town’s steep hills. In May and June, the countryside is a vivid, electric green. In September and October, the air smells of fermenting grapes, and the hills turn to gold and ochre.

Vibe: Perfect “walking” weather (18°C–24°C). This is the prime time for photography and vineyard tours.

Note: These are the most popular months, so expect moderate crowds and higher hotel prices.

2. The Festival High: Late August

Key Date: August 30, 2026 (The last Sunday of August).

The Event: The Bravìo delle Botti. The town transforms into a medieval theater as the eight districts compete in a grueling uphill barrel race.

Vibe: Electric, loud, and crowded. The entire week leading up to the race features candlelit processions, flag-throwing, and district dinners in the streets.

Weather: It will be hot (often 30°C+), and the town will be packed. Book accommodation months in advance if you want to be in the center.

3. The Wine Lover’s Window: Autumn Harvest

Months: September and October.

The Draw: This is the Vendemmia (grape harvest). You can witness the activity in the vineyards and enjoy the Festa dell’Uva e del Vino (Wine and Grape Festival) in nearby Chiusi or local tastings in Montepulciano.

Food: October also kicks off truffle and chestnut season, meaning the local trattorie menus are at their absolute best.

4. The Quiet Season: Winter

Months: November to March.

The Christmas Market: From late November through January 6th, Montepulciano hosts one of the largest and most famous Christmas Markets in Italy, featuring a “Santa Claus Castle” in the Fortezza.

Why: If you want the town to yourself, this is it. You can wander the Piazza Grande in total silence.

Vibe: Moody and romantic. It’s perfect for cozying up in an underground cellar or visiting the nearby thermal baths (Terme di Montepulciano) to escape the chill.

We recommend 7-10 days based on what you want to see and do. We offer flexible vacation packages so you can select your number of nights in each city, desired hotel and activities. We suggest a minimum of 3 nights in larger cities.