Pre-Aperitivo Aperitivo, 5:05 pm

This corner of central Italy is achingly beautiful in the winter, especially at night when thick, menacing fog rolls in, dampening the scent of burning leaves and brush. When I step out of the car, I take a moment to breathe it in, and then promptly head inside to change and join Alberto for a drink by the fire. 

Alberto and his brother Amedeo (who is doing something he thinks is better than hanging out with us—a decision that we intend to make him regret) oversee the creation of some spectacular bottles at Tenuta Sette Ponti. But tonight we are set on having fun and not thinking about work. 

I try to bring spirits as an offering when I’m a guest in a house that has an infinite amount of fine wine. On this occasion it’s a tin of Gin Engine, Paolo Dalla Mora’s gin, packaged in what looks like a mini drum of automotive oil, made with Sicilian lemon peel, Piemontese sage and the best juniper in the world—which is to say, Tuscan. Our G&Ts do their designated job of opening up the appetite. And we’re off to the city.

7 pm (AKA Time to Get Serious)

Osteria Grande, as it is named in jest, is in fact a tiny sliver of a restaurant. But its size belies the ambition that stands behind it. It’s well worth visiting for a special meal if only to find out what ambitious creations the young Chef Fatjon Goga is offering. And if you’re on a mission to drink Arezzo dry, you can do very well there with cocktails alone. 

The drinks menu is as serious as their dinner menu: it is imagined as an itinerary, which suits us perfectly on this particular evening. Though there are several house creations that tempt me, I decide to anchor to a gin-base and go for a Negroni, fashioned with the elite Bianco Ambrato Vermouth from Mancino. Alberto, who is generously sticking with one of their equally adventurous non-alcoholic options to stay in shape for getting us home, suggests I somewhat incongruously pair my Negroni with one of the Gillardeau oysters they offer as a bar snack. Rapture ensues.

8:30 pm Cocktail Hour(s) Continue

As set forth originally, this evening was meant to be a party, so I’m not sure why I end up genuinely shocked when Alberto guides me into the corded-off VIP section of an establishment that reads very early aughts Meatpacking in the best way. Divò Cocktail Club is vibrating with music and people both inside and out, and when we roll up to the back bar I realize why. Danny Del Monaco, expert in all things Italian cocktails, is pouring. As Alberto’s guest I have the rare privilege of watching this master of mixology build drinks expressly for me.

In a particularly clever twist of didactic prowess, Danny works his way up and down the bar, making essentially the same cocktail five times (in miniature, for decorum’s sake), but each time swapping out just one ingredient so we can clock the specific role it plays in the finished product. This included an Americano, Negroni, Manhattan, Old Fashioned and Boulevardier. I am extra delighted by this since it speaks to the professional teacher in me as much as to the professional drinker, and find myself truly moved by how much I’m learning while having fun.

10 pm, Getting Hungry

Dinner is habitually late in Italy, of course, especially by American standards. But we’re in a small city in winter and I think we might be pushing it when we finally make it into Buca di San Francesco, a classic Tuscan trattoria tucked underneath Arezzo’s fourteenth-century basilica that houses “The Legend of the True Cross,” the spectacular fresco cycle painted by Piero della Francesca. On the contrary, like everywhere we’ve been tonight, the restaurant is bustling, and only gets more densely packed with chic fashion-industry types as our meal progresses.

I am bestowed with the honor of choosing the wine. Since we’re having a traditional Tuscan menu, if ever there was a moment for Sangiovese it’s now. I opt for a favorite standby, Castello di Monsanto Chianti Classico, and then Alberto surprises me with a deep cut from his cellar: the 2012 Tenuta Sette Ponti Oreno. It’s always exciting to taste an older vintage, but in this case it’s especially so, as Oreno is right now in the midst of a transformation to better reflect the new generation at the winery’s helm. This richer, headier version of the wine catapults me into a reverie about the deep past of winemaking around Arezzo, and in short order I’m face first in a T-bone completely unaware of myself or the world around me. Alberto gets a photo for future embarrassment, and then—after I get most of the beef tallow off my face—we take a selfie to remember how much fun we had, just in case our memories are blurry after we get home and polish off the rest of the gin.