Before I began planning this trip Montepulciano was a name I only knew from wine bottles. Was it a place? A grape? I never gave it much thought. Ironically enough the city of Montepulciano has nothing to do with the vast majority of wine bottles exported from Italy that carry that name. The most well-known Montepulciano of wine refers to a grape variety grown mainly in Abruzzo and other provinces of central and southern Italy. Montepulciano grapes are rarely grown in Tuscany and never in the vicinity of the city of Montepulciano. Plenty of wine is produced around the city of Montepulciano but it is from Sangiovese grapes and is labeled Vino Nobile di Montepulciano or Rosso di Montepulciano. This quirk of naming results in a great deal of confusion for foreign tourists who are accustomed to the cheaper, heavily exported Abruzzo wines and are shocked by the high prices of the local Montepulciano reds. 
Like most of the medieval towns in the region, Montepulciano sits at the top of a hill and has a sloping layout. Our Airbnb was located on Via Fiorita at the lower, northern end of the town, close to the Prato gate. Our Airbnb host had insisted on having her property manager meet us in person to provide us access, an annoying practice that is virtually extinct in the United States but still persists to some degree in Europe. That had required us to make a stop in Montepulciano to pick up our keys before completing our day's itinerary, but it hadn't inconvenienced us tremendously. The apartment was on a third level walk-up which was another minor annoyance but we were pleased with the space itself, a pleasantly-decorated and spacious two bedroom with a dignified atmosphere and a tile floor.
After checking in with the manager we immediately returned to the car to visit the thermal baths at Bagno Vignoni and have dinner in Pienza as described in the previous post. On Tuesday morning we set off along a side street with the simple goal of reaching the other end of the town, armed only with a short list of sights not to be missed.
We soon found ourselves on the Spalto della Mura promenade at the eastern edge of the town, looking out at the Val d'Orcia over a low stone wall. We could see the rest of the town gently rising uphill ahead of us, topped by the clocktower of the Palazzo Comunale. Montepulciano was originally founded by the Etruscans around 500 years B.C. Over successive centuries it was controlled by the Romans, the Lombards, the Sienese and the Florentines until the unification of Italy in the nineteenth century.
There was no market that morning (the weekly event is on Thursdays in Montepulciano) and we were in need of a place of breakfast. One level below us on the hillside we spotted an absolutely beautiful cafe called l'Ortolano, which is a term that refers to a fruit and vegetable gardener. True to its name the cafe displayed rows of colorful and fresh produce and also advertised panini. We found our way to the staircase that led downhill and found a beautifully arranged store with all kinds of local delicacies from wine and cheese to salumi and preserves. The fruit was offered at tourist prices but the panini were quite reasonable and we found combinations to suit everyone's taste. One of the sauce options for the panini was called 'nduja, which sounded vaguely African. I looked it up and discovered it was a spicy pork sausage paste that originated from Calabria in southern Italy. I had also seen the term Chianina used to describe beef products suck as steak and hamburger. I finally looked it up and determined it was the name of a prized local breed of cattle. It was somewhat similar to classifying beef dishes as Angus or Kobe. We leisurely ate our breakfast on the shady patio as cars zoomed by on the busy road that led into town.
Now fortified we continued on our way until we reached the far end of the narrow plateau. This area had the majority of the town's sights and the heaviest concentration of exclusive hotels and restaurants. I was taking notes of the most enticing restaurants we passed as I had made no plans yet for dinner that night. Many buildings were decorated with elaborate arrangements of plants and flowers. We also encountered the usual lavender shops and some interesting art galleries.
The views from the southern edge of the ridge were likewise extraordinary. The geography of Tuscany with its patchwork of valleys interspersed with high ridges was certainly conducive to some breathtaking scenery. We could have spent an entire morning just walking the circumference of the town and appreciating the view from every angle.
The town's ancient fortress has been converted into a multifunctional site occupied by a university campus, exhibition spaces, and a wine-tasting showroom. During our visit the grounds were dotted with whimsical bronze dogs by the German sculptor Carin Grudda. 
The Enoliteca showroom was established by a local consortium of wine producers and offers a dizzying variety of local wines that are provided via automatic dispensers. It was a similar set-up to what we had seen in the wine shop in Montalcino but much more extensive. The showroom was rather plain with cafeteria style tables but it was lined with dozens of dispensers, each loaded with eight different bottles. Hundreds more bottles were arranged in cabinets and shelving above the dispensers. Some of the flooring had been replaced with a transparent material under which we could see stone wells. There solitary staff member present told us these were the ruins of Roman storage vats for water and oil that had been uncovered during the construction of the showroom. She gave us a card charged with a hundred euros, and we would only be charged with what we spent. It seemed like an ingenious method to get people to spend a hundred euros on wine very quickly. We selected our first bottle by the prettiest label and pushed the button for the smallest pour, a five euro charge. Such a tiny amount of wine issued that we couldn't believe it. We pressed the button a couple more times in case the machine had malfunctioned. The wine barely covered the bottom of the glass, about as much as a waiter pours for the customer to test the bottle. We selected a second bottle because it had the plainest label and only cost three euros and the exact same amount of wine was dispensed. The amount of wine was about an ounce, a twenty-fifth of a bottle or a fifth of a standard glass of wine at a restaurant. The pours were valuing the bottles at about a hundred euros apiece. Considering that we were pouring our own wine without the assistance of a waiter and in a room with the ambiance of a cafeteria the price was ridiculous. I can't speak much to the wine which wasn't to our taste. Our preferences run counter to the general categorization of red wines which is that higher quality corresponds to longer periods of aging in oak barrels. Northern Italian wines are typically aged in oak, like Bordeaux and California cabernet sauvignons, which to us makes them taste like liquid tree bark. We prefer southern Italian wines that are mellower and fruitier like Primitivo and Nero d'Avola. We're basically heathens but we're glad we enjoy some of the cheapest wines that are available in the US. 
Having crossed the town on its edge via the promenade above the walls we decided to return by the main arteries that passed through the center. We soon arrived at Piazza Grande which was dominated by the gray ashlar and travertine cube of the Palazzo Comunale and its imposing clock tower. The six hundred year old building still houses Montepulciano's municipal government. The piazza was occupied by a stage and seating for a classical music festival that had begun several days earlier. Some of the other architectural gems surrounding the square were the neoclassical Palazzo Nobili-Tarugi and the stately Cattedrale di Santa Maria Assunta.
Walking north on Via Ricci we came across a beautiful confectionery called Dolce Vita. Fortunately the kids were still satiated from breakfast and we only had to get them bubble teas. Via Ricci ended at the piazza outside the Orfanotrofio Antoniano orphanage. Here we got our first view from the western edge of the town which may have been of the northern edge of the Val d'Orcia or the southern edge of the Val di Chiano, there was no way to be sure. Either way the orderly patchwork of fields and olive groves was spellbinding.
Leaving this piazza along Via del Poggiolo brought us to a corner of the town that was colorful, peaceful, and off the tourist track. By the time we wandered into the tiny Piazza di Santa Lucia there were no other pedestrians in sight and we had the magnificent baroque facade of the Chiesa di Santa Lucia all to ourselves. Just a block further we found ourselves in a neighborhood where all the buildings were made of brick instead of stone, perhaps a later addition to the medieval city. The most striking example was the distinctive belltower of the Chiesa di Sant'Agostino.
From here we spilled back into Via di Gracciano nel Corso, the main artery of the northern part of the town. This brought us to Piazza Michelozzo, the location of the renowned Torre di Pulcinella. The mystery of the automaton that rings the bell of the tower is that he wears the mask and costume of Pulcinella, a traditional comedic figure of Neapolitan puppet theater. It is believed that a seventeenth century restoration of the tower was influenced by a priest or benefactor from Naples leading to the incongruous character placement. I saw that the clock on the tower was reading ten minutes to two although my phone indicated it was a quarter to two. It didn't seem like long to wait to see the mechanism in action, although I wasn't sure if it would occur at the time on the clock or at the actual moment of two o'clock. Fortunately I had my camera trained on the figure when the minute hand hit twelve and sure enough the figure struck the clock twice. I was the only one watching and filming, probably because the real show was at noon when there were twelve strikes. I didn't realize until I looked at my footage that the automaton was striking the bell with a mallet in his right hand rather than the spear prominently displayed in his left.
Continuing onward on the same street we soon passed in front of La Vineria di Montepulciano. I had this on my list of desirable restaurants but we still weren't very hungry. I poked my head inside for a look and the place seemed so inviting with its vaulted brick ceilings and arrays of cheese and salumi that I couldn't resist grabbing a table. We justified our presence with a couple of soups and one pasta dish. I made the mistake of asking for a beer and the waiter replied that they didn't serve it, almost unable to hide his revulsion at just the mention of that non-oenological beverage. Shortly after leaving La Vineria we arrived at Colonna del Marzocca, a five hundred year old Roman column topped with a stone lion that signified the town's allegiance to Florence. This meant we were back at Piazza Savonarola, the square right by our Airbnb, and our tour of the city had come to an end.
We went back to the Airbnb to freshen up and grab a few supplies and made our way back to the parking lot. I noted with relief that we didn't have a parking ticket, confirming that the white lines really did mean that there was for some unfathomable reason a free section in the paid lot. We had one stop to make before heading towards Cortona. In the valley just below the town stood the spectacular sixteenth century Sanctuary of the Madonna di San Biagio. As we drove on the straight road towards the church we passed through a double line of tall cypress trees. The church was enormous and looked as though it had been carved from a solid block of travertine. Its Greek Cross design is reminiscent of St. Peter's Basilica in the Vatican. The sanctuary's construction was ordered after reports of a miracle at the old parish church that originally occupied the space. 
Even though it felt like we'd already been exploring for a full day it was still only one thirty in the afternoon. We still had time to see at least two more towns in Tuscany that day and we were going to make the most of it.
This featured blog entry was written by zzlangerhans from the blog Fledgling Explorers.
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