Exploring Italy, Pt. 4: Montepulciano (2023)

Picking up from the prior Italy post, Rome is in our rearview mirror as we head north, to the Tuscany region. Our specific destination is Montepulciano, 111 miles (179 km) away, so the drive will take a couple hours.

Along the way, we stop and take a look at some of the hilltop towns. Orte is one of those, and the lands nearby have an interesting history. In BC times, two major battles were fought between the Etruscans and Romans on the shores of Lake Vadimone. Today, the standard Google Maps view depicts water covering a small area, but the satellite photos only reveal farmland, since the lake, of volcanic origin, has receded underground over the millennia.

Another hilltop town along the way is Civita di Bagnoregio. I wish we had time to visit this unique destination (the pedestrian-only access is via a long footbridge), but our ultimate goal is arriving in Montepulciano before all the shops close for the day.

An hour later, this final destination is in sight. What's initially surprising to me about Montepulciano is the elevation, at 1984 ft. / 605 m. As always, I do a ton of research before our trips, and I sure didn't realize the drive takes you up higher and higher via switchback roads. The view of the Tuscan countryside below is commanding and, in a way, brings to mind some of the views from the Great Smoky Mountains.

Among the hills and trees along the road, our GPS signal keeps cutting out. When it picks back up, the suggested path into town has changed, taking us through a parking lot. A ZTL (“limited traffic zone” - read more about that here) comes into view, and with hesitation, we drive on in, since our hotel is in town.

Clearly, the narrow space between the buildings indicates these streets were built long before cars were invented, and we have to fold in the mirrors so they don’t scrape against someone’s front door. When the pavement turns into gravel, it really feels like we aren’t on the right path. We make a brief, international call to the hotel, and they help us determine we’ve entered the wrong ZTL zone. Thanks for nothing, GPS! At this point, we wonder if the town will eventually send us a fine for driving in an unpermitted area. Our more pressing concern is gunning the car back up the steep, gravel path without sliding right off the side of this hill town.

We find enough traction to kick some pebbles behind us and exit the town alive. Circling its perimeter, we gain more elevation and finally reach the south entrance. From here, the car rattles over the cobblestone streets until we arrive at the hotel. The first impression is that it’s clean, modern, and nice. There are photos on the wall of some “Twilight” actors that stayed here while filming part of the “New Moon” movie.

Our room, on the other hand, really leaves a lot to be desired. Have you ever visited any elderly people who live in an old house and, although the place looks clean, the decor is dated, and the bathroom has a weird, musty smell? This place is like that. 

The comforter has a flower print that was probably popular in the ‘80s. The wall AC unit might be missing the remote, as I can’t change any of the settings, and it only blows out hot air. When trying to connect to wifi, my tablet warns of weak security. Yikes.

We try to rush on out of here - not just because the room is depressing - but because our arrival was later than we had hoped. After all, this is the famous Tuscan wine region, and most of the shops in town will be closing soon, at 6 PM.

At the top of our wine list, thanks to our favorite TV travel host, Rick Steves, is Cantine Contucci. We head straight there. Like a number of the other tasting rooms in town, this one has a maze of subterranean, cave-like passageways, where the wine is aged in massive barrels. The self-guided tour is free, and you can buy bottles of wine or a tasting on the way out. Being from California, we’re used to some sort of deal, like the tasting being comped if you buy at least a couple bottles… That isn’t the case here, so we just buy one from the six we try, pay for our tasting, and get moving along, in search of more wine.

Down the street (literally “down” the big hill that is Montepulciano), we find a shop that’s open until… 10 PM? Can that be right? It seems counter to the Italian spirit of only marginally giving in to capitalism (except for visiting the Blue Grotto, described in "Pt. 1"). I can’t help but wonder if the workaround for staying open late in a place like this is to employ students from the U.S. studying abroad (Kennesaw State University, for example, has a presence here).

At Cantina Ercolani, we wander through another series of subterranean corridors and re-emerge back in the tasting room. Here, at this place open later than everywhere else around, we are offered free tastes of wine, oils, and spreads. Like at the shop before, we buy another bottle of Vino Nobile di Montepulciano. It has a DOCG label, which is basically a government stamp guaranteeing this wine was made only from grapes grown on the surrounding hillsides. From there, it rests and ages in the cellars below our feet. We also buy a delicious red pepper spread, which we hope to reverse-engineer for ourselves at home.

We still need to figure out dinner, and I really want to try Florentine steak ("bistecca alla fiorentina”) while in Tuscany. It’s a huge cut from a young steer or heifer and grilled only until it’s rare. From a lot of research, the consensus is that the place to order this regional speciality while in Montepulciano is from Osteria Acquacheta. It’s hard to book a reservation at that restaurant, though. You can only call so, two months out, we emailed our hotel and asked if they could book a spot on our behalf. “Sorry, there are no more reservations available for that evening,” they reported back.

Fast forward two months later, to “that evening” (tonight)... We walk by the place, and it’s closed! Consider how situations are sometime handled in this part of the world, I’m not exactly shocked to report there’s no sign on the door, saying “We will be closed this week for vacation,” “We are currently closed due to staffing issues,” “We will be closed today due to a family emergency,” or anything at all. I’m glad we couldn’t book a reservation after all.

So, now, where should we go for dinner? We pull out our phones and see what other restaurants have Florentine steak… Caffè Poliziano is a couple streets away. Great! Let’s go there!

The dining room offers a really beautiful view of the Tuscan countryside down below. Jumping straight to the more important matter, though, their Florentine steak isn’t good. The roughly €50/$50 cut of beef is overcooked, tough, and fatty. It looks enticing, but only about 5% of it was enjoyable. Before the steak arrived, a man at the table sitting behind me asked if theirs could be cut up, and he muttered something about an electric carving knife. Beware of this place, and keep in mind there other restaurants in town that serve Florentine steak. Also, none of the house wine is available tonight, which means we can't order a carafe or single glasses - only bottles of wine you’ve likely never heard of.

In the morning, this small city offers a quiet stillness. It’s a time before the usual tourists fill the streets and before the hot, summer sun beats down and heats up the cobblestone walkways. There isn’t much better than being on vacation, sitting at a cafe table on a side street in Tuscany, with a flaky croissant in one hand and an espresso in the other.

Our trip to Montepulciano was a quick one. Now, we need to lug our suitcases down a long, gravel path, load up the car, and get a move on to one of my favorite places anywhere: San Gimignano.

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"Exploring Italy, Pt. 4: Montepulciano (2023)"

Written by: Justin Kilmer

Critiqued by: Janine Kilmer

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