_{This is part 3 in a series. If you’d like to read Part 1: Orvieto or Part 2: Massa & Cinque Terre, be my guest.}

One of the most awkward moments of our trip happened when I stopped to fill up on gas on our way to Montepulciano. I was already getting a little worked up because Katie was hungry (reminding me frequently) and we couldn’t find a place to grab a snack, so conditions were perfect for an uncomfortable scenario. I spotted a gas station off the autostrade that had a bar, so I pulled in.

Right away, I felt like a moron because the gas tank was on the opposite side of what I’m used to. I knew this, so I didn’t pull in the wrong way, but as I approached the pump, I still felt like I was doing something wrong. When I walked around the car, I immediately didn’t know how to open the gas tank – no switch, no indentation, no handle. Deciding I’d figure it out later, I tried to find English instructions for how to use the pump (there were none) when a very tall, very angry Italian woman wearing a uniform came over and quickly established herself as a gas station attendant.

“FULL!?” she grunted at me. At this point, I was already nervous and confused so I didn’t understand her. I asked her if she spoke English: “Parli Inglese?” Her already enormous frown grew even deeper and she again barked, “FULL!?” Finally understanding, I sighed with relief, agreed and said “Sì, grazie” (Yes, thank you). She magically got my gas tank opened and jerked out the diesel handle. I stopped her and said no diesel, to which she frowned somehow even bigger, grabbed my arm and pulled me close. She pointed to the tank that said – in plain English, no less — that the vehicle took diesel fuel. I apologized – mi dispiace.

When she finished pumping the fuel, I began looking for a place to pay on the pump – there wasn’t one. My ferocious Italian friend barked at me “YOU PAY INSIDE!” and while this was awkward, I was grateful to have an excuse to walk away from her. Inside the bar, found some good-looking croissants and alerted the clerk that I needed help. I pointed to one particularly delicious-looking pastry and said “questo … due, per favore” (This … two, please). She looked terribly confused so I repeated myself. Her face remained scrunched up. I know I said it right … I went for English: “Two, please.” She finally informed me in half-Italian that there was only one pastry.

My bad. 

I asked for that and one other pastry, paid for my hard-earned diesel fuel and finally got out of there with my tail tucked firmly between my legs. We were gassed up and Katie had a snack. All was right in the world again.

On the outskirts of Montepulciano, it was lunchtime and too early to check in, so we bummed around the nearby town of Siena. We found a spot called Caffe’ del ‘900 which seemed like a quaint corner restaurant that served the locals of that community – no frills and very much like an old country restaurant in East Tennessee. Katie ordered Tagliatelle al Ragu (boar ragu) and I got the Maltagliati al Ragu Biacno e Tartufo (pasta with white truffle sauce). I hate that we didn’t snap photos here, because it definitely felt like a “locals only” gem and the food was excellent.

From there, we headed to a nearby big-box grocery store called Coop. We knew we’d be in Montepulciano for several days so getting some treats for the room was essential. This was more-or-less just like going to a half-sized Publix only with about 10 times the amount of cured meats. I was also thrilled to see little individually wrapped slices of pizza just chilling in a basket for people to pick up.

At Coop, we picked up tortellini mignon (mini tortellini), mousse tartufo (truffle mousse), salsa agione (seasoned marinara sauce), salsa al carciofi (artichoke sauce), crostini, speck and brie gnocchi, crema di salmone (salmon paté), pollo e potate insalata (chicken-and-potato salad), pecorino, capers, focaccia and some dessert tarts. We were very proud of our selections, but the clerk at the checkout line wasn’t.

He only spoke Italian (phrases I didn’t understand) and became frustrated when we didn’t know what to do with our basket. After scanning all of our items and slinging them down the chute, he asked if we needed a bag. When we said yes, he ripped off a single plastic bag and, literally, threw it at us. We bagged what we could in our single plastic bag, stacked everything else and got the hell out of there.

Back in the car and ten minutes later, we were on a one-lane gravel road in the country. We’d reached Montepulciano and there were vineyards as far as the eye could see. Montepulciano is a medieval and Renaissance hill town in the Tuscan region of Italy. It’s a very important agricultural area in this part of the country and is well known for its wine production. Fortunately for us, our agriturismo was a working vineyard called Podere La Rocca. This place was incredible as most rooms were more-or-less apartments located on the top floor of the agriturismo’s existing structures, but we had the one-and-only standalone cottage.

We wanted to relax but we were told during check-in that there was going to be a wine tasting at 5pm so we toughed it out and made our way over. We ended up making friends with two other couples – one from Newfoundland and the other from British Columbia. We enjoyed three types of red wine with a variety of breads, cheeses and cured meats before they brought us a fourth sample: the first port we’d ever tried, paired with a delicious almond biscotti. This may have been my favorite drink of the whole trip.

After that, we retreated to our cottage for long baths and Prosecco. Katie hit the kitchen afterward with our single bag of groceries and whipped up our tortellini mignon with capers and salsa al carciofi. She served it with some of our fresh focaccia. I was kind of loving these “homemade” dinners during our trip!

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The next day was a day we’d been looking forward to. We’d scheduled a pasta-making class with the on-site restaurant’s owner, Head Chef Federico. Our friends from British Columbia joined us for the lesson that would include ravioli, pici, tagliatelle and pappardelle. 

We began by making the dough for the ravioli, tagliatelle and pappardelle. This was very simple and consisted of only flour and eggs. After we worked our dough, we wrapped it in clingfilm and laid them out to rest. Next, we each made a small batch of pici dough, which was simply flour, stone-ground flour, water and egg. Once we each had our dough balls complete, Chef Federico combined them and we each took turns working the large dough ball. Once complete, that dough ball was laid to rest and we revisited our other work in progress.

After flouring our surface and rolling pins, we rolled our dough into a small rectangle, then meticulously ran it through the pasta press. By the time the pressing was done, we had a pasta sheet a couple of feet long! We cut this sheet in half, laid half on a tray to be used for the ravioli, then began rolling the other up from each side until it met in the middle. From there, we used our knives to cut ribbons of various widths from fettuccine to tagliatelle to pappardelle. Chef Federico taught us a fun party trick where you run your knife under your cuts and lift it to reveal your pasta masterpiece.

From there, we laid out our ravioli sheet, cut it in half, brushed one side with water, then began piping in a combination of ricotta cheese, spinach, salt and pepper – about a tablespoon per dollop. From there, we layered on top the second sheet and made a rough press to indicate where the ravioli should be cut. Next, we used a dedicated cutter to carve out our ravioli pieces, hand-pressed them and laid them out on a sheet.

Finally, Chef Federico took our remaining dough ball and began cutting off little slivers for each of us to work into pici. This was accomplished by pinching one side of the sliver and pulling while simultaneously rolling with the opposite hand to create what ultimately results in a fat spaghetti. We each rolled out between 8-10 strands of pici and laid them out on another tray. With this, our work was done. All that was left was to enjoy the fruits of our labor.

We joined our Canadian friends at a table and Chef Frederico poured us each a glass of wine. Meanwhile, the team in the kitchen got to work preparing our pasta dishes. First up: our ravioli. This was a great example of just how perfect Italian food is with its simplicity. The pasta was stuffed with the very simple cheese mixture, then cooked in a combination of butter and sage. This was my personal favorite of the day.

Next, our pici was brought out with an equally simple sauce made from tomatoes, olive oil and garlic. Finally, our remaining pasta was tossed together in a more complex meat sauce – we’d learned that fatter pasta lends itself more fully to meatier sauces, especially those that are wild-game based. This was phenomenal.

After some napping in the cottage, we suited up for what was sure to be an exciting – and tasty – night at the on-site restaurant. We immediately became friends with our server Antonio, who brought us a delectable orange wine with a box of various breads, crackers and biscuits. We ordered fried artichokes from the antipasti menu and were blown away by what we received! Each artichoke was tempura-fried and ate very much like a fried chicken wing.

Our main course that night was Bistecca Fiorentina (Steak Florentine), a staple that originated in that area. The enormous t-bone steak landed on our table with a side of lard-based garlic sauce for dipping and a hot plate to be used for rewarming our slices of steak should we need it. We ordered a side of cheesy potatoes, which made for a lot of food but we finished it all with smiles on our faces. We somehow found room for the Chocolate Beignets with Mousse for dessert.

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The next day was dedicated to touring Florence. About 45 minutes away, I was a bundle of nerves because our assigned parking garage’s location required me to drive on roads where driving is illegal. Supposedly, the garage tracks your license plate and reports it to the city so you don’t get a ticket. I took their word for it and nervously navigated the stone streets I could barely fit on.

Florence is the capital of the Toscana region and is a hotbed of Renaissance history. Everything from the streets to the walls and windows of every building we passed was beautiful and elegant in its own way. And thankfully, we were guided by a precious soul named Anna, who took care of us around every possible corner.

We began our tour at an Art Deco bar called Giacosa 1815, which while not the bar that invented the Negroni, is in the same location as the bar that did! It was still early, so we opted for espressos. We popped into a leather store where I bought Katie an authentic Italian leather jacket, then did some sight-seeing of the many sculptures that line Piazza della Signoria before getting to see original art by da Vinci, Michelangelo and Botticelli at Galleria degli Uffizi.

After our art museum experience, Anna took us to a pizzeria inside a clothing store called Menchetti for what she said was the best pizza in town. Katie got her trademark focaccia sandwich while I enjoyed a sausage pizza. Anna didn’t steer us wrong!

Pizza Count: 5

From there, we hit a world-famous gelateria called Vivoli. Katie had been wanting to try affogato and I was just happy to be there. She got what she wanted and I enjoyed a cup of caramel gelato. The place was packed and we quickly learned why – this place’s gelato was the best of the trip!

The second “big” part of our trip to Florence was visiting David at the Galleria dell’Accademia, which changed my life in so many ways. This is a food post and not an art post, but just know that this is worth every penny and every second you spend there. I was at a loss for words for the first time just being in his presence.

Shortly after this, Anna bid us arrivederci, leaving us to tour on our own for a bit. We stopped at a record store bar called Move On where we took some selfies and snacked on popcorn with our Limoncello Spritzes. 

Before we left Florence, we stopped by one of the famous wine windows, this particular one at Osteria Belle Donne, and tried our first-ever chianti. We were pretty hyped to finally get to utilize a wine window, but the wine left a lot to be desired. It was also kind of awkward to just stand on the sidewalk with a bunch of other people sipping wine from plastic cups. It was like we were on a smoke break outside a shitty dive bar only it was wine and not PBR.

That night, back at the cottage, Katie popped back into the kitchen and made our stuffed gnocchi with marinara sauce. There was a fairly rowdy birthday party going on at the restaurant merely steps away from our bedroom, but we didn’t care. We split the last of the desserts and dozed off after a very long day.

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Our final full day in Montepulciano was designed for rest. We ate a fairly large breakfast (continental) and spent the day watching comedy specials in bed and washing our clothes in the bathroom tub. We were looking forward to another amazing meal with Antonio in the restaurant, but before dinner, Katie decided we should do our own aperitivi on our cottage’s front porch.

We’d snatched some fresh pears from the buffet at breakfast (grown on-site) so we cut those up and served them on a large platter with salmon paté on crostini with capers, leftover pastries from breakfast, slices of different Italian cheeses and some mozzarella-prosciutto crepes we’d picked up at Coop. We paired all of this with a bottle of rosé we’d been chilling. It was pleasantly cool out and we were dressed to kill. This is one of my favorite memories from our trip.

For dinner that night, at the behest of our server and head chef, I ordered Pea Risotto with Goat Cheese, Ginger and Sweetbreads. If you know that sweetbreads are animal organs (I did), you may snarl your nose at such a thing, but believe me when I tell you this was one of the most delicious things I had on our whole trip! Katie ordered Carbonara-Filled Ravioli topped with Black Garlic Sauce and Pecorino Cheese Fondue and she loved hers just as much as I loved mine. Most nights we’d split each other’s dish so we could get equal time trying different things, but this was a “one bite, then I’m eating the rest” kind of night for us both.

We finished things off that night with a Saffron-Pear Tartlet served with Homemade Vanilla Gelato, Raisins, Pine Nuts and Licorice.

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The next day, we packed and hit the continental breakfast one last time. It was definitely a bittersweet moment because we were very excited to hit the road for Assisi, but we’d fallen in love with our cottage, the restaurant staff and the little town of Montepulciano. Little did we know that things were still – somehow – going to get even better.