I pulled into the parking lot just below the Porta al Prato, the late afternoon sun casting long shadows across the chalky ridge that divides the Val d’Orcia from the Val di Chiana. Montepulciano is a Renaissance hilltown on that ridge, and from the first step through the stone gate, I understood why it’s often called one of the finest winemaking regions in the world, with its superb vineyards stretching out in every direction. The walk uphill to Piazza Grande is a steady climb, but every turn reveals another view that makes you stop and pull out your camera.
Montepulciano sits on a chalky ridge dividing the Val D’Orcia from the Val di Chiana, celebrated for its superb vineyards and considered one of the finest winemaking regions in the world.
Is Montepulciano worth the hype? Yes, but not for the reasons you might think. The wine is excellent, but the real draw is the town itself — compact, walkable, and genuinely lived-in, not just a tourist stage set.
Wine lovers
Solo travelers
Couples
Piazza Grande and the heart of the hilltown
The central square is where Montepulciano’s medieval and Renaissance layers meet.
Piazza Grande is surrounded by the Palazzo Comunale and the Montepulciano Cathedral, also known as the Cathedral of Santa Maria Assunta, which dates to the 16th century. The cathedral’s interior is simpler than you might expect from a Tuscan church, but it holds an impressive altarpiece and religious icons that reward a quiet look. I spent a good twenty minutes just standing in the square, watching locals cross with shopping bags and a few tourists snapping photos of the Palazzo Comunale’s tower.
The Palazzo Comunale itself is worth a climb if you have the legs for it — the view from the top stretches across the Val d’Orcia and the Val di Chiana, giving you a real sense of why this hilltop location was chosen. Just outside the town walls, the Church of San Biagio stands on its own, designed by Antonio da Sangallo the elder. Michelangelo referenced the Temple of San Biagio when drafting St Peter’s Basilica in Rome, which is a fun fact to drop on your travel companions.
Vino Nobile di Montepulciano and the historic cellars
Wine is the reason many people come here, and the cellars are as historic as the churches.
Vino Nobile di Montepulciano is a red wine with esteemed appellation status, produced from grapes grown in the surrounding vineyards. The historic cellars are architecturally significant, often carved into the tufa rock beneath the town, and they attract both wine lovers and aesthetes. I visited Avignonesi and Boscarelli, two of the most notable wineries, and both offered tastings that paired the wine with local pecorino cheese and cured meats.
The wine itself is fuller and more structured than Chianti, with a depth that surprised me. If you’re planning a tasting, spring and fall are the best times to visit due to pleasant weather and fewer crowds. Summer can be hot and busy, especially during the Bravio delle Botti in August, when teams race wine barrels through the historic streets in a celebration of local rivalry and spirit.
Book your wine tastings in advance, especially at smaller cellars like Boscarelli, which only take a few groups per day. Walk-ins are rare in peak season.
Walking the cobbled lanes and finding the views
The real magic of Montepulciano is in the walking.
The historic center is compact and walkable, with cobbled lanes stretching from the city gates to panoramic viewpoints overlooking the vineyards. Via di Gracciano and Via dell’Opio nel Corso are the main arteries, lined with cafes, artisan shops, and historic buildings. I spent an entire morning just wandering, stopping for a coffee at a tiny bar where the owner remembered my order after one visit.
The views from the eastern edge of town, near the Church of San Biagio, are the ones you see on postcards — rolling hills, cypress trees, and vineyards that seem to go on forever. It’s also a great spot for photography, especially in the golden hour before sunset. If you’re traveling with kids, the walk uphill can be tiring, but the reward at the top is worth the whining.
The historic center is car-free, so you’ll park outside the walls and walk in. Parking lots are clearly marked, and most are a 5-10 minute walk from Porta al Prato.
What to eat and where to eat it
Tuscan cuisine is simple, and Montepulciano does it well.
Local dishes include pici pasta with garlic sauce, grilled Chianina steak, and Cinta Senese sausage. I had pici cacio e pepe at a trattoria near Piazza Grande, and it was the best version I’ve had outside of Rome. The pasta is hand-rolled, thicker than spaghetti, and holds the sauce in a way that feels almost unfair to other pasta shapes.
For a full meal, expect to pay around €30-40 per person for a starter, main, and a glass of Vino Nobile. Lunch is the best value, with many places offering a fixed-price menu that includes a first course, second course, and water or wine. Dinner is more formal and pricier, but the quality is consistent across most restaurants in the historic center.
Day trips from Montepulciano: Pienza, Cortona, and thermal baths
The town is a great base for exploring southern Tuscany.
Pienza is about a 20-minute drive and is famous for its pecorino cheese and Renaissance architecture. Cortona is a bit farther, around 40 minutes, and offers a more rugged hilltown experience with Etruscan roots. Bagno Vignoni, a thermal bath village, is only 15 minutes away and is a perfect afternoon stop for a soak after a day of walking.
If you have a car, you can easily visit all three in a single day, but I’d recommend picking two and taking your time. The roads are winding and narrow, and rushing through these towns defeats the purpose of being in Tuscany. For a longer trip, consider a weekend itinerary that includes Siena, Montepulciano, and Pienza as a movie — a 141 km route that covers three legs and some of the best scenery in the region.
Parking in Pienza and Cortona can be a nightmare in summer. Arrive before 10 AM or after 4 PM to avoid the worst of it. Bagno Vignoni has a small public parking lot that fills up fast on weekends.
Getting to Montepulciano: car vs. train
Your choice of transport shapes your entire trip.
Montepulciano is approximately 120 km from Florence Airport (FLR) and about 200 km from Rome’s Fiumicino Airport (FCO). Traveling by car is recommended for flexibility, especially if you plan to visit nearby towns. The drive from Florence takes about 1.5 hours, and from Rome about 2.5 hours, depending on traffic.
Public transportation involves taking a train to Chiusi-Chianciano Terme Train Station, then a 30-minute taxi ride to the town. The train is cheaper but less convenient, especially if you’re carrying luggage or traveling with kids. I drove, and I’m glad I did — having a car meant I could stop at a random vineyard on the way back to our apartment.
| Option | Time from Florence | Cost (approx) | Best for |
|---|---|---|---|
| Car rental | 1.5 hours | €50-80/day | Flexibility, day trips |
| Train + taxi | 2-2.5 hours | €25-40/person | Budget travelers, solo |
- Drive if you can — it unlocks the best day trips and lets you stop at vineyards on a whim.
- Book wine tastings in advance, especially at smaller cellars like Boscarelli.
- Visit in spring or fall for the best weather and fewest crowds.
Before you visit Montepulciano
Is Montepulciano too touristy?
It can be, especially in August during the Bravio delle Botti festival. The main streets fill up with day-trippers from Florence and Rome. Visit in the early morning or late afternoon to avoid the worst crowds.
How many days do you need in Montepulciano?
Two days is ideal — one for the town itself and one for day trips to Pienza, Cortona, or Bagno Vignoni. If you’re short on time, a single day is enough to see the main sights and do a wine tasting.
Is Montepulciano walkable for kids or older travelers?
The historic center is all uphill, and the cobblestones are uneven. Strollers are possible but challenging. Older travelers should take it slow and use the benches scattered along the main streets.
What’s the biggest disappointment about Montepulciano?
The parking situation. Lots fill up fast, and some are a 10-minute walk from the gate. If you arrive after 11 AM in summer, you might circle for 20 minutes before finding a spot.
Can you visit Montepulciano without a car?
Yes, but it’s less convenient. The train to Chiusi-Chianciano Terme plus a taxi works, but you’ll miss the flexibility to explore the countryside. Consider a guided wine tour that includes transport.
Why Montepulciano stays with you
I’ve been to a lot of Tuscan hilltowns, and Montepulciano is the one I keep thinking about. It’s not the biggest or the most famous, but it has a quiet confidence that makes you want to stay longer. The wine helps, sure, but it’s the way the town feels lived-in — the old man reading a newspaper in Piazza Grande, the cat sleeping on a windowsill, the smell of wood smoke from a restaurant kitchen. That’s the Tuscany I came for. For more ideas on where to go next, check out my guide to Tuscany’s medieval hilltop towns.
Sources and further reading
Visit Tuscany. “Montepulciano.” 🔗
Itimaker. “Montepulciano Itinerary.” 🔗
Dining and Cooking. “Why Montepulciano Is Italy’s Most Coveted Hidden Gem.” 🔗
Related reading on Emily in Italy
Experience Luxurious Italian Train Travel from Rome to Tuscany — Covers the train route from Rome to Tuscany, including stops near Montepulciano, with tips on booking and what to expect.
Verona, Florence, Tuscany, and Rome: A Northern to Central Italy Journey — A broader itinerary that includes Tuscany and can help you plan a longer trip that incorporates Montepulciano.
Italy’s Timeless Charm: 15 Unmissable Destinations for 2026 — A list of top destinations across Italy, with Montepulciano featured as a standout Tuscan town.