Castellina in Chianti & Etruscan Tombs

Medieval hilltop village with Etruscan tombs beneath. The underground passages (Via delle Volte) are ancient. Wine estates surround the village in every direction.

What to do there

5 things to do

1. 1 Walk Into a 2,700-Year-Old Tomb — For Free Adventure · Free

   This 53-meter-diameter burial mound dates to the 7th-6th century BC — built when Rome was still village huts on the Tiber. Four tombs carved into earth, each entrance oriented to cardinal points, where Etruscan aristocrats of the Orientalizing period were buried with parade chariots decorated in bronze and imported Attic vases. Walk to the circular grass mound just outside the village on SR 222 toward Greve in Chianti (impossible to miss), push the light timer switch inside the entrance gate, and step down the dromos into burial chambers where four family members have lain since the 600s BC. The same hills visible through the entry are draped in Sangiovese — descendants of vines the Etruscans planted.

   Backup: If gate appears locked, check with the Rocca museum (Piazza del Comune 19) — they sometimes manage access. The site is technically always accessible during daylight.

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2. 2 Walk Brunelleschi's Secret — The World's First Gunpowder-Proof Tunnel History · Free

   In 1431, after Visconti forces devastated the town, Florence sent Filippo Brunelleschi — the man who built the cathedral dome — to fortify Castellina. What he designed was history's first underground passage engineered to withstand gunpowder explosions. Via delle Volte runs as a semicircle beneath the medieval walls (accessible from either end of Via Ferruccio), and its loopholes aren't decorative — they're firing positions from when Sienese and Neapolitan forces besieged this town for 44 days in 1452. Walk the full 200 meters slowly, stopping at each slit cut through stone where defenders looked out at exactly the view you see today.

   Backup: The tunnel is always open (it's a public street). If any section is blocked due to works, walk Via Ferruccio itself — the main street runs parallel and connects to the Rocca.

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3. 3 Climb the Rocca Tower and Find the Etruscan Vine Seeds History · Price: low

   Inside this Florence-built fortress that withstood a 44-day siege by a coalition of Siena, Naples, Spain, and Pope Sixtus IV in 1452, find the ceremonial chariot reconstruction from the Montecalvario tumulus — parade-quality bronze work from 600 BC. Then ask to see the vine seeds: domesticated Vitis vinifera pips dating to the 4th-3rd century BC from these same Chianti hills, pressed into wine by people dead 2,300 years before you arrived. The Etruscans didn't just coexist with wine in Chianti — they created the tradition you taste in every glass of Chianti Classico. At Rocca di Castellina, Piazza del Comune 19, climb to the crenellated tower for 360-degree vineyard views.

   Backup: If museum is closed (winter weekdays), the Rocca exterior and tower base are freely visible. The view from Via delle Volte's loopholes provides a partial equivalent.

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4. 4 Order Pici al Cinghiale in a Trattoria That's Been Here Since 1922 Adventure · Price: low

   Pici al ragù di cinghiale at this family-run trattoria connects you to 1922, when Mussolini ran Italy and the Chianti Classico Consortium was just founding its Black Rooster symbol. Pici is thick, hand-rolled spaghetti made fresh daily by Tuscan grandmothers since medieval times; wild boar have roamed these hills since before the Etruscans. The slow-cooked, deeply savory, dark-stained ragù arrives with house Chianti Classico at Antica Trattoria La Torre, Piazza del Comune, right at the foot of the Rocca. Request terrace seating — eating beneath the fortress tower is continuity, not just lunch.

   Backup: Osteria La Gramola on Via delle Volte is the alternative — rustic-chic, with pappardelle cinghiale and truffle gnocchi. Equally local, slightly more upscale.

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5. 5 Taste the Wine That Comes With an Endangered Bird on the Label Wine · Price: moderate

   Since 1977, Castellare di Castellina has featured a different endangered bird on each vintage label — partnership with the Italian League for Bird Protection on a property where synthetic chemicals are banned. Their I Sodi di San Niccolò ('the hard-to-till land') was created in the early 1980s to prove native Sangiovese could match the 'Super Tuscans,' and it did. Meanwhile, 2,700 meters away, those Etruscan vine seeds in the museum prove someone was making wine from these same hills in the 4th century BC. At Strada Provinciale di Castagnoli SP 130 Loc. Caselle (2km from village center), or visit Tenute Squarcialupi's 15th-century cellars IN the village at Via Ferruccio 28.

   Backup: Querceto di Castellina (organic since 2012, family-run, 11.5 hectares) accepts by appointment: +39 0577 733590. Their LIVIA Wine & Cheese Bar terrace has vineyard views.

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Insider tips

• Montecalvario Etruscan tomb is just outside town

• Via delle Volte is a medieval tunnel worth exploring

• Book tastings at nearby estates in advance

• Sunset from the Rocca (fortress) is stunning