As soon as I stepped into the Grant Hyatt New York for the Chianti Masterclass, my heart sank. I’d come expecting a Chianti Classico event, a gathering of the great and mighty from this legendary zone between Florence and Siena. Instead, here was a cast of outliers—47 wineries with unfamiliar names from Siena, Arezzo, Pistoia, Prato, and Pisa. I felt like I’d mistakenly arrived at the wrong cocktail party on the outskirts of town. Worse yet, I felt gypped of the opportunity to taste some really great wine.

What a snob you are, I then thought, wondering where I’d picked up such a dismissive attitude towards “the other Chiantis.” It took only a second to realize—it was in Chianti Classico itself.

Chianti Classico & the "other" Chiantis
I’d completely absorbed their oft-repeated narrative, which goes like this: Chianti Classico is the original territory for Chianti wine, its borders first defined in 1716 by the Grand Duke Cosimo III dei Medici and circumscribing Gaiole, Radda, and Castellina. Here, it’s said, the terrain is more mountainous, the soil rockier, the wines more powerful—Chianti at its best. It was here in the 1800s that Bettino Ricasoli of CASTELLO BROLIO first identified sangiovese as the superior grape among indigenous varieties, recognizing that it had the right stuff for age-worthy wines—those appropriate to the dignified guests he’d soon be entertaining as Prime Minister of the newly created nation of Italy.

But as Chianti’s fame spread, the surrounding territories started jumping on the bandwagon and using its name to sell their simpler wines. The peeved producers in the historic heartland felt it diluted their brand and pushed back. The result was the creation of the Chianti Classico zone in 1932, while outliers were given new names indicative of geography, mostly hills (colli). Today seven Chianti zones encircle the Classico territory: Colli Aretini (the hills of Arezzo), Colli Fiorentini (Florence), Colli Senesi (Siena), Colline Pisane (Pisa), Montalbano (near Monte Albano in Pistoia), Rufina (northeast of Florence), and Montespertoli (southwest of Florence). All fall within a broader DOCG (denominazione di origine controllata e garantita) that takes the name of “Chianti” plain and simple. Producers within each subregion can append their name, such as “Chianti Colli Senesi.”

Meanwhile, at the panel discussion....
Complicated, I know. So are the evolving DOCG rules that dictate grapes, blends, and aging. Predictably, the panel discussion during our master class revolved around such details. As we tasted, wine pros in the audience grilled the panelists about the percentage of sangiovese in each blend (by law, between 70 to 100 percent); about the prevalence of merlot as a supporting player (it softens sangiovese’s aggressive tannins without competing with its perfumes); about the use of French barrique versus Slavonian cask for aging. The usual stuff.

While all this helps explain why a wine tastes the way it does, it only goes so far towards understanding it. Why has Chianti endured as one of the most recognizable wine names in the world? For me, the idea of Chianti clicked into place at a certain moment in the discussion.

“Do people want to know what grapes are in the Chianti?” the moderator asked Dan Amatazzi, wine director at EATALY, Mario Batali’s Italian food emporium.

“No. They ask what’s on sale,” he replied. That got a laugh, but then he continued with a more revealing point: “The customers bring in stories—about their visits to Tuscany, about wines they had on vacation. If they want a Chianti, they’ll get a Chianti; they don’t want to know grapes or regions.”

This is what the Chianti Classico narrative misses: People want a memory trigger, a way to travel back to that cozy trattoria in Florence where they ate penne and drank wine served in a rooster-shaped carafe. It doesn’t matter whether it was a Chianti or a Chianti Classico. And chances are, it was a basic, quaffable Chianti—nothing special, but something that went great with their pasta and augmented the glow they felt after a memorable day under the Tuscan sun.

What's your Chianti moment?
Thinking back, I can pinpoint my own Chianti moment, the one that got me interested in wine. It was at the Pensione Bandini, where I lived when studying in Florence. Two resident Italian law students were in the habit of bringing a crusty loaf of bread, a round of fresh pecorino, and an unlabeled bottle of wine to the fifth-floor loggia at magic hour. A few of us Americans would join them. Watching the swallows dive over the angular landscape of terracotta rooftops, we’d try to bridge the language gap. I don’t remember our conversations, but I do remember that wine. It was fresh, delicious, and nothing like the dreadful plonk I’d tentatively explored during high school. I remember thinking, This actually tastes like grapes! Today I might call it fruit-forward, young, and simple. But “simple” doesn’t diminish its rightness. There are times when simple is good: A Tuscan sunset. Swallows careening in their circular dance. Church bells tolling in a Renaissance campanile. A young Chianti sipped on a loggia with friends.

Mind you, not all Chiantis are simple and young. There’s a huge range, due to the fact that some 3,600 wineries make Chianti (that’s in addition to the 350in Chianti Classico). Indeed, three-quarters of Tuscany falls inside the Chianti DOCG zone, the largest in Italy.

A few good wines
That’s why it is possible to find examples that are as powerful and structured as the best Classicos. At this tasting, CASTELVECCHIO Chianti Colli Fiorentini Riserva was a case in point: a powerhouse wine with sangiovese’s characteristic amarena cherry flavors, ample tannins, and a judicious touch of vanilla. Castelvecchio lies just 200 meters from the border of Chianti Classico and tastes like it.

Then there were wines like MANETTI PAOLO’s Chianti and Chianti Sammontana from FATTORIA DI SAMMONTANA, exemplars ofgood, traditional, lighter bodied Chianti. Both had that transparent crimson color that defines sangiovese and offered tart cherry and cranberry flavors, fine sandy tannins, and an appealing earthiness. Like Tuscany in a suitcase, they’re the type that transport you back to that rustic osteria in Florence or Pisa or Siena that you so loved.

Speaking with the head of the CONSORZIO VINO CHIANTI, Giovanni Busi (who makes a delicious Chianti Rufina under the TRAVIGNOLI label), I asked how to wrap one’s head around all these Chianti denominations. Was it better to explore region by region? To break it down by blends?

“No, begin with the producer,” he insisted. Though one may learn that, say, Rufina has the highest elevation and greatest temperature excursion (which sangiovese loves), resulting in its reputation as the best among the “other” Chianti zones, “Rufina” in itself is no guarantee of anything, he notes. “It’s producer, producer, producer.”

At $12–$20 a bottle, it doesn’t cost a fortune to sample through the outer regions of Chianti. Just ask a trusted wine shop to pick out some favorites. What’s nice is that Chianti still offers terrific value as a wine. As a ticket to Tuscany, it’s priceless.

(A version of this story first appeared in UNCORKED on May 8.)