Is Montepulciano Worth Visiting? Our Favorite Hill Town in Tuscany
We lived in Florence for a year and every time friends or family came to visit, this was one of the first places we brought them. No matter how many times we made the drive, it never lost its magic.
It's not the biggest name, not the most photographed and not the easiest to get to. It's just the town that gives you the most for a single day. You can spend the morning exploring centuries-old wine cellars, linger over lunch with vineyard views, walk the medieval streets and finish in Piazza Grande without ever feeling rushed.
After living in Tuscany and returning here again and again over the years, it's still the hill town we recommend first.
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Our Tip
Arrive hungry, wear comfortable shoes and don't rush to the top. Some of our favorite moments in Montepulciano happened halfway up the hill, wandering into centuries-old wine cellars, stopping for a glass of Vino Nobile and ducking into little shops that weren't on our itinerary.
Why Visit Montepulciano?
What makes Montepulciano different is how simple it is to explore. Unlike many Tuscan hill towns, you don't need an itinerary. The old city is essentially one main street that climbs from the bottom of the hill to the Fortezza and Piazza Grande at the top. Most of what you'll come here to see is along that route, which means you can spend less time looking at maps and more time enjoying the town.
Ceramics shops. Small restaurants. Wine bars built into old stone buildings. The town is known for Vino Nobile di Montepulciano, made from Sangiovese, and it's one of our favorite Italian wines, full stop. It also happens to be historically significant. Vino Nobile was the first Italian wine ever awarded DOCG status, back in 1980, the highest classification Italian wine can get. Winemakers here had already been making serious, age-worthy wine for centuries by the time the classification caught up to them.
So here's how you spend a few hours in Montepulciano: walk that street with a glass of wine in your hand, stop at whichever door looks interesting, keep going until you hit the top. That's it. That's the whole plan, and it works.
Best Things to Do in Montepulciano
You don't need an itinerary packed with attractions to enjoy Montepulciano. Most of the fun comes from wandering the main street, ducking into old wine cellars and stopping whenever something catches your eye. These are the places we wouldn't miss.
Wander the Main Street
Don't rush.
The walk from the lower gate to Piazza Grande is Montepulciano.
You'll pass tiny wine bars, family-run restaurants, artisan shops and narrow alleyways that seem to disappear into another century.
We've walked this street on nearly every visit to Montepulciano and somehow always end up discovering something new. Sometimes it's a tiny wine bar. Sometimes it's a hidden courtyard. Sometimes it's an alley we'd swear wasn't there the last time.
Montepulciano reminds us a little of Cortona. They're completely different towns, but both reward slowing down instead of racing between attractions. If you're exploring Tuscany by car, they're an easy pair to include on the same trip.
Explore the Underground Wine Cellars
Before you make it to Piazza Grande, spend some time underground.
Near the bottom of the main street, before the climb even starts, there's a way down into the old wine cellars carved into the hillside. Some date back to the 1200s. It's a quick stop, worth doing before you start drinking your way up the hill, because it gives you a real sense of what winemaking here actually looked like centuries before Vino Nobile had a name.
Dylan was far more interested in the barrels than the history lesson.
Try Vino Nobile di Montepulciano
You really can't visit Montepulciano without trying the wine that made the town famous.
We almost always end up stopping somewhere along the main street for a glass before lunch. It's become part of our routine.
Vino Nobile is one of our favorite Italian wines and there's something special about drinking it only a few steps from where it's been produced for generations.
If you're planning to explore more of Tuscany's famous wine regions, continue on to Montalcino, home of Brunello, another one of Italy's iconic wines. Comparing the two towns makes for a fantastic day or overnight trip.
Visit Piazza Grande
Eventually you'll reach Piazza Grande, the heart of Montepulciano.
Surrounded by Renaissance buildings, the cathedral and the Palazzo Comunale, it's one of the most beautiful squares in Tuscany and the place where everyone eventually seems to gather.
Somehow we always spend more time in Piazza Grande as we think we will.
We tell ourselves we'll just take a quick look before heading back down the hill, then twenty minutes later we're still sitting on the steps with a gelato watching everyone else walk by.
No matter how many times we've been, it never feels like a place you rush through.
If you're planning to visit Siena as well, you'll notice the two piazzas couldn't feel more different. Siena's Piazza del Campo is grand, lively and unmistakably urban, while Montepulciano's Piazza Grande feels quieter and more intimate.
Don't Forget to Look Up
Most people walk into Piazza Grande looking straight ahead.
Look up instead.
Above the historic clock you'll spot Pulcinella, the traditional figure who rings the bell every hour. It's one of those little details that's easy to miss, but once you know it's there you'll probably find yourself hanging around to watch it happen.
We certainly did.
It's a small moment, but it's exactly the kind of thing we remember long after we've forgotten what time we got there.
A Christmas Market Worth Planning a Trip Around
We've visited Christmas markets all over Europe and Montepulciano is still one of our favorites.
The market spreads around the Fortezza with wooden chalets, festive lights and plenty of local food and wine, but what really makes it special is the setting. Instead of feeling like a market that's been dropped into a town square, it feels like the entire town celebrates Christmas together.
One year we visited with Dylan, who happily wrote a letter to Santa inside the fortress while we shopped around in the market with hot chocolate in hand. Looking around at the lights, the old stone buildings and families enjoying the afternoon together, it felt more like a Christmas village than a Christmas market.
If you're planning a December trip, we'd absolutely include Montepulciano in your itinerary. It's also one of our favorite stops in our guide to the Best Christmas Markets in Europe.
Experience the Bravio delle Botti
Montepulciano has one of the more physical festivals in Tuscany. The Bravio delle Botti happens every year on the last Sunday of August. Eight of the town's historic neighborhoods, called contrade, compete by rolling 80-kilogram wine barrels roughly 1,800 meters through the streets, most of it uphill, on that same steep main street we just told you to wine taste up. Two runners per team push and steer. Whoever wins takes home a painted banner in a ceremony back in Piazza Grande.
The tradition traces back to a medieval horse race that got banned in the 1600s over safety concerns. A local priest revived it in 1974, minus the horses, and it's been an August fixture ever since.
We haven't made it to this one ourselves. But knowing that street, we genuinely can't picture how hard that climb is even without a few hundred pounds of wine barrel attached to it. Like most of these neighborhood competitions in Tuscany, this is real local pride, not a show staged for tourists.
Yes, Twilight Fans, This Is the Town
Even if you're not a Twilight fan, you've probably seen Montepulciano before.
Many of the scenes in The Twilight Saga: New Moon that were supposed to take place in Volterra were actually filmed here in Piazza Grande.
The first time we realized it, it made perfect sense. Standing in the square, surrounded by Renaissance buildings, it already feels like a movie set.
Where We Ate
One of our favorite meals in Tuscany happened at Ristorante Degli Archi.
We originally stopped because of the view.
The terrace overlooks the Tuscan countryside and after spending the morning wandering uphill, it seemed like the perfect place to settle in for lunch.
Then something happened we weren't expecting.
Halfway through our meal, the owner started singing opera.
It's still one of those travel memories we laugh about years later.
The restaurant itself has a wonderfully quirky interior, the food was excellent and the views were every bit as memorable as we'd hoped.
If we were back in Montepulciano tomorrow, this is where we'd have lunch again.
Where to Stay in Montepulciano
If you enjoy walking everywhere, stay inside the historic center. Boutique hotels tucked into old stone buildings put everything within a few minutes' walk.
If you're dreaming of vineyards, cypress trees and long evenings with a glass of wine, stay just outside town instead.
If you're still deciding where to base yourself, compare Montepulciano with Pienza, Montalcino and Siena. They each offer a completely different experience, and choosing the right one depends on how you want to explore Tuscany.
Getting There and Parking
Like most Tuscan hill towns, Montepulciano is easiest to visit by car.
The drive from Florence takes around 90 minutes, while Siena is about an hour away. Although there are train stations nearby, they aren't within walking distance of the historic center, so you'll still need a bus or taxi for the final stretch.
Parking was actually much easier than we expected.
Our biggest challenge wasn't finding a space. It was figuring out how to pay.
On our first visit we stood staring at the parking machine for several minutes, completely convinced we were doing something wrong. Eventually another visitor walked over, showed us exactly what to press and we were on our way.
If you're driving in Italy for the first time, don't stress if it takes a minute to figure things out. Chances are someone nearby has been in exactly the same situation and will happily point you in the right direction.
Once you've parked, everything is done on foot.
The old town is closed to most traffic and, because everything follows one main street uphill, it's almost impossible to get lost.
A Note If You're Traveling Solo, With a Partner or Slowing Down
Montepulciano is one of the easiest Tuscan hill towns to explore at your own pace.
Because the historic center follows one main street, there isn't any pressure to rush between attractions or constantly check a map. Explore for a while, stop for a coffee, browse a few shops or enjoy a leisurely wine tasting. You'll still make it to Piazza Grande with plenty of time to enjoy the views.
The only thing to keep in mind is the climb.
The street is steep and the cobblestones can be uneven in places, so comfortable shoes are essential. Take your time and enjoy the walk. Some of the best views and shops are found before you even reach the top.
Know Before You Go
When to visit: Any time of year works, but December for the Christmas market and warm months for outdoor wine tasting are both good reasons to go. The last Sunday of August brings the Bravio delle Botti, and it will be hot and crowded.
How to get there: A car, or a tour or transfer from a base like Florence, Siena, or one of the other larger Tuscan towns. No direct train.
How to get around once you're there: Park at the top or bottom and walk. It's one main street, so you're not going to get lost.
What to book ahead: Nothing is strictly required, but if you want a tasting with a specific winemaker, email ahead, especially in peak summer or around the Bravio delle Botti weekend.
What to pack: Comfortable, sturdy shoes. The street is steep and the stones are uneven, especially if you're wine tasting your way up. Bring a light jacket even in shoulder season, since the wind picks up at the top of the hill.
Pair it with: Montalcino and Pienza are both close enough to fold into the same day trip if you're based nearby.
Planning More Tuscany Travel
We'll be adding more from our time in Tuscany soon, including guides to Montalcino, Cortona, and San Gimignano. In the meantime, check out our Italy Travel Guide for more of the regions we know best.
