When I have the opportunity to prove that Chianti Classico can show grace and pristine fruit quality akin to Red Burgundy, I use Giovanna Morganti's Le Boncie as my first example. I implore you to trust this will be your moment of clarity for Sangiovese.

Importer Neal Rosenthal's Montevertine is a benchmark for the region, but his other discovery, Le Trame, better illustrates Sangiovese's sometimes elusive, fruit-forward profile and silken tannins. Also consider Chiesamonti, which comes from a one-hectare parcel in Castelnuovo Berardenga. The stonier soils here result in a wine with brighter red fruits and a long saline finish (Differing from Giovanna's other wines that exhibit more fleshy characteristics). These two Chiantis are all class.

Giovanna farms her five hectares using organic and biodynamic principles. I could go down the rabbit hole on farming, fermentation, and aging specifics, but I'd like to cut this one short and say: This is a profound wine that's a joy to drink. I've lost count of the number of times I've used this bottling to convince friends that Sangiovese can be fun, approachable, and deadly serious. Below is a photo from my 2017 visit and the gorgeous color of the Stockinger barrel sample that had me in love.

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Toscana lovers are likely familiar with Radda because of Montevertine’s Le Pergole Torte or Monteraponi (Two estates we’ve heavily cited here at KWM over the years). They have brought worldwide attention to this small village, and for good reason. But these days, true Chianti enthusiasts are turning to another name: Paolo Cianferoni of Caparsa. These 100% Sangiovese wines still fly under the radar, for now, but they’re quickly gaining notoriety, as you’ll see from Antonio Galloni’s recent reviews.

Chianti from Radda is distinctly known for its elegance and finesse, and it’s no different in the case of Caparsa. Though traditional in every sense, Paolo’s natural-leaning tendencies and his devotion to preserving his estate’s sense of place—the flora and fauna, microorganisms, and soils, as Paolo says—truly shine through in bottle. These wines will transport you to Radda! They’re pure, vibrant, and have a quiet but fierce wildness too. The Rosso di Caparsa, which only sees cement, is high-toned and cherry fruit-forward, while the plush, neutral barrel-aged Mimma shows a fuller spectrum of red-black fruit, green olive, cedar, and blood.

The Cianferoni family has been growing Sangiovese in Radda for as long as its more famous neighbors. Paolo’s father, formerly a professor at the University of Florence, purchased and planted vines at Caparsa in the 1960s. Still impacted by World War II, much of Tuscany lay abandoned, but the Cianferonis stuck to their inclination. Paolo, with his wife and children, took over in 1982 and introduced organic farming. From the same importer who has brought us our top-selling Italian discoveries in recent years, including Amorotti in Abruzzo and Paso Delle Tortore in Campania, Caparsa is our latest reference point for Radda.

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Fontodi is the poster child of everything positive achieved in Chianti Classico with modernization. In 1968, the Manetti family purchased this property and ushered the Panzano zone into the minds of collectors, showing a "Super Tuscan" could still be super without resigning to blending international varieties like Cabernet Sauvignon and Merlot with native Sangiovese.

Atop the Conca d'Oro, Fontodi's vines bask in the sun in this northern property at 450 meters above sea level. The estate's oldest vines mainly grow on porous and fragile gaelstro soil and go into the flagship Flaccianello. Walking throughout this immaculate, pristine cuverie and cellar, I was reminded of Bordeaux's influence on the region. Aging for the flagship Falccianello takes place in 100% new French barrique. Normally, this would be a turn-off for me in Chianti, but the mastery of integrating this wood has earned Fontodi the respect of traditional-leaning collectors for decades.

It's not often that I find myself reaching for the more modern examples of Sangiovese, but without a doubt, Flaccianello is where to turn for Chianti at its most stately and refined. The track record of Flaccianello in the cellar is legendary. Today, bottles from the 1980s are still fresh and offer thrilling drinking experiences.

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From Rome through Florence, top restaurant wine lists all find a space for these age-worthy Chianti Classicos from vintages stretching back to the early 70's. This is where the longevity and transformative capabilities of Sangiovese are best illustrated. During my trip to Tuscany in 2016, no estate garnered the same respect from winemakers and sommeliers quite like Castell'in Villa.

Castell'in Villa doesn't fall into any easy category other than being staunchly traditional in their vinification and aging. The estate's soil has an unusual makeup of fossilized fragments that conjure Chablis more than Tuscany. The profound mineral aspect combined with the structure from these choice old vines, dedicated to the Riserva, arguably makes for one of the most sought-after aged wines in Tuscany.

Greek Princess, Coralia Pignatelli della Leonessa, has overseen the property here for many years, residing in the 13th-century tower above the winery. She keeps a healthy stock of back vintages, namely the epic 1971 Chianti Classico Riserva that's still found on top Michelin starred wine lists in Italy.

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