While millions flock to Florence and Siena, Tuscany’s true charm lies in its small
hillside villages, where centuries-old wine traditions thrive alongside modern-day
dolce vita.
These hidden gems offer authentic experiences of Tuscan life, from morning
espresso in ancient piazzas to evening wine tastings in medieval cellars.
Montalcino
Perched high above rolling vineyards, this birthplace of Brunello wine combines
medieval architecture with world-class vintages. The imposing 14th-century fortress
offers wine tastings with sweeping valley views, while family-run enotecas serve
locally sourced wild boar alongside their famous red wines.
Castellina in Chianti
This ancient Etruscan settlement sits along the historic Via Chiantigiana wine road.
The underground Via delle Volte tunnel street provides cool refuge on summer days
while surrounding vineyards offer intimate tastings of traditional Chianti Classico.
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Montepulciano
Famous for its noble Vino Nobile, this Renaissance hill town rises dramatically above
the Val d’Orcia. Historic wine cellars tunnel deep beneath the streets, while the main
square’s caffès provide perfect spots for evening passeggiata people-watching.
Panzano in Chianti
Home to celebrity butcher Dario Cecchini, this village combines wine culture with
exceptional cuisine. The Sunday market fills the main square with local products,
while nearby organic wineries lead the region’s biodynamic movement.
San Gimignano
Known for its medieval towers and white Vernaccia wine, this village feels frozen in
time. The historic center comes alive during evening aperitivo, while family wineries
in the surrounding countryside welcome visitors for intimate tastings.
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Radda in Chianti
Ancient stone walls encircle this classic Chianti town where traditional wine-making
methods prevail. The historic Chianti Classico consortium headquarters occupies a
former monastery, while nearby agriturismos offer wine-focused accommodation
among the vines.
Greve in Chianti
The triangular Piazza Matteotti serves as the heart of this wine-trading village. The
famous Antica Macelleria Falorni still cures meats traditionally, while the surrounding
hills host some of Chianti’s oldest family estates.
Volpaia
This fortified village has transformed its medieval buildings into a modern winery
while maintaining its historic character. Ancient wine cellars connect beneath the
streets, while the village restaurant serves traditional dishes made from estate-grown
ingredients.
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Castelnuovo Berardenga
Located at Chianti’s eastern edge, this village offers sweeping views toward Siena.
The impressive Villa di Geggiano welcomes visitors for tours and tastings, while the
surrounding countryside provides excellent hiking through vineyards.
Gaiole in Chianti
Once ranked as Europe’s most idyllic place to live, this village maintains its peaceful
character. The annual L’Eroica vintage bicycle race celebrates local traditions while
historic castles turned wineries dot the surrounding hills.
Castellina Marittima
This coastal wine village offers a unique perspective on Tuscan vintages. Sea
breezes influence the local wines’ character, while spectacular sunsets over the
Mediterranean provide perfect evening entertainment.
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Carmignano
This small village produces one of Tuscany’s oldest protected wines, dating back to
Medici declarations. Local producers still blend Sangiovese with Cabernet Franc
following centuries-old traditions, while Renaissance villas offer elegant tasting
experiences.
Bolgheri
Famous for Super Tuscan wines, this coastal village charms with its cypress-lined
avenue. Medieval streets house excellent wine bars and restaurants, while
prestigious estates along the Via Bolgherese welcome serious wine enthusiasts.
Vicopisano
This medieval village combines wine heritage with olive oil production. The perfectly
preserved Brunelleschi fortress towers over ancient streets, while family estates
produce excellent wines from hillside vineyards.
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Artimino
Nestled below a Medici hunting villa, this village preserves traditional Carmignano
wine production. The local wine museum explains centuries of viticulture history,
while estate tastings offer views across olive groves to Florence.
Riparbella
This hidden gem in the Pisan Hills produces excellent yet little-known wines. Organic
vineyards stretch toward the sea, while agriturismo stays offer authentic farm-to-
table experiences among the vines.
Civitella Marittima
Perched high in the Maremma hills, this village offers a glimpse of rural Tuscan life.
Small family wineries welcome visitors like old friends, while the local cooperative
preserves traditional wine-making methods.
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San Casciano dei Bagni
This thermal village combines wine culture with ancient Roman baths. Family
vineyards produce excellent wines for local consumption, while thermal pools
provide relaxation after wine-tasting adventures.
Explore Austria’s Tranquil Lake Villages
Whether you’re a serious wine enthusiast or simply seeking the authentic rhythm of
Tuscan life, these villages offer experiences that go far beyond typical tourist trails.
Take time to explore slowly, chat with locals, and discover your favorite corner of
Tuscany’s wine country.
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