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Siena & Chianti

Wine fans should base themselves in the south of Chianti, a landscape that bucks the Tuscan trend with hills, often forested, that are more imposing than rolling, and topped by smaller chic villages. Holidays don’t get much more relaxing than pootling up, down and around these heavy hills, pulling over for a wine-tasting or a hearty Tuscan lunch. The area centres on three villages, Castellina in Chianti, Radda in Chianti and Gaiole in Chianti, but Panzano further north (technically in Florentine Chianti but spiritually southern) is making a foodie name for itself thanks to the butcher and restaurateur Dario Cecchini. Southern Chianti puts you within easy reach, too, of that Renaissance jewel, Siena. This city is famed for its shell-shaped Piazza del Campo, where tumultuous crowds cheer on the Palio horse race, but its treasures also include the Pinacoteca Nazionale gallery, which is filled with breathtaking art by the likes of Duccio and Simone Martini.

Siena & Chianti

San Gimignano

San Gimignano, bristling with ancient towers, is often dubbed the `medieval Manhattan.’  The skyline has scarcely changed since the Middle Ages - yet the famous towers do, indeed, resemble miniature skyscrapers. San Gimignano’s towers were built in the 12th and 13th centuries by the magnati, or nobles, during the Guelf-Ghibelline conflicts. These windowless towers protected the wealthiest families in times of strife: families could retreat into the many rooms inside for months at a time. As well as defending the city, the towers served as status symbols: the higher the tower, the richer and more powerful its owner. Given its spectacular setting, San Gimignano is one of the most touristy towns in Tuscany but manages to rise above the masses. Come for its medieval mood but try and linger after the tour buses have left town. Reward yourself with a toast to medieval glory – in local Vernaccia wine, of course.

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San Gusme

San Gusmè, a walled hilltop hamlet, is a charming Sienese backwater. Set 5 km north of Castelnuovo Berardenga, this tranquil spot has always been in Siena’s orbit. The medieval village only joined the Grand Duchy of Tuscany in the 16th century, after Siena’s definitive defeat. The Sienese gateway still bears Siena’s coat of arms, the Balzana. Stretches of the defensive walls remain, with parts incorporated into gateways. The hamlet is a place for picturesque views, including of the Sienese skyline, the Torre del Mangia and Siena Cathedral. This sleepy hamlet is more about mood than specific sites. Admire the church of Saint Cosmus and Damian, the local patron saints, and the church of Santissima Annunziata, with its quaint bell tower. Wander along concentric alleys, lapping up the timeless mood before retreating to a gourmet inn for creative cuisine or a homely café for wine and a plate of cured meats.

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Castellina in Chianti

Castellina is one of the most charming hilltop villages in the Chianti. Set on the scenic Chiantigiana, it surveys symmetrical vineyards and wooded groves, a landscape dotted with low stone houses and ancient wine estates. Castellina’s name reveals its medieval function as a Florentine outpost. In the late 13th century it was the first site of the Chianti League, a group of three Florentine feudal castles, each responsible for a third of the territory. This strategic stronghold fell to a Sienese-Aragonese siege in 1478 but after Siena in turn fell in 1555, Castellina became a picturesque backwater. Tucked into its fortifications, Castellina looks much as it did in the 15th century. La Rocca, the mighty fortress, is now the town hall and home to a small archaeological museum, with tempting wine shops nearby. The circuit of walls encloses a warren of atmospheric backstreets with half-glimpsed views of the Chianti hills.

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Castagnoli

Castagnoli, south of Gaiole in Chianti, is a small, stone-built village surmounted by a medieval fortress. Known as the Rocca di Castagnoli, this stark fortress was besieged by the Sienese in 1478. This is Chianti castle country, with Castagnoli surveying Castello di Meleto, a medieval outpost which is now centred on a wine estate, even if the castle itself is also open for visits. From both the Rocca and the village extend views of spindly cypresses, olive groves, olives and vineyards. Rocca di Castagnoli wines are worth sampling before you set off to explore grander Chianti Classico estates. The countryside from Castagnoli south to Siena and east to Arezzo is higher, wilder and wetter. The wooded peaks are green and fresh with the scents of thyme, rosemary and pine. Deep chestnut woods provide ideal cover for wild boar, which often end up on your plate, paired by the local wines.

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Radda in Chianti

If Greve is the commercial brain of Chianti, Radda is its soul. With its small-town mood, picturesque Radda makes an appealing base for exploring wine country. Given its prime position between Gaiole and Castellina, Radda served as the capital of Chianti, and was the medieval capital of the Chianti League. The fortifications reflect Radda’s history as a borderlands and bulwark against Sienese attacks. Peace finally came to this area after Siena was incorporated into the Republic of Florence in 1559. Hilltop Radda retains its medieval street plan and imposing town hall. Formerly known as the Palazzo del Podesta, the 16th-century town hall displays heraldic shields on its façade. Radda is still bound by its defensive walls, with cobblestoned alleys fanning out from the main square. Today’s mellow scene is centred on the Casa Chianti Classico, a showcase for everything wine-related so come here to make sense of the Chianti spirit.

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Gaiole in Chianti

Hilly Gaiole is, of course, wine country but also castle country and cycling country. A decade ago, this sleepy market town was dubbed the world’s most idyllic place to live. Not much has changed since then so lap up the quality of life. This market hub is forever linked to the Ricasoli wine dynasty, whose ancestors supposedly launched the Chianti Classico brand in Brolio Castle. Apart from boasting of being the birthplace of Chianti Classico, Gaiole is celebrated in its own right. In medieval times it was one of the three capitals of the Chianti League, along with Castellina and Radda. The hilltop town is set among oak and chestnut forests but also surveys vineyards and olive groves. As a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys. The triangular-shaped main square is a stepping-stone to explorations of castles, cosy inns, wine estates and ancient abbeys.

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Castelnuovo Berardenga

Castelnuovo Berardenga sits on the southern border of the Chianti, somewhat overshadowed by Siena. For better or worse, its fortunes have always been tied to Siena. In 1555 this Sienese stronghold lost its encircling walls when Siena was defeated by the Florentine-led Medici Grand Duchy. Today, Castelnuovo is special for its peaceful atmosphere and sense of an authentic Tuscan style of living. The low-key charms include a couple of minor churches and a clocktower, remodelled from the original fortifications. Admire Vicolo dell'Arco, with its steep stone staircase and decorative arch. Such charms won’t detain you for long but it’s a soothing spot for contemplating the slow pace of life outside bigger Tuscan towns. In fact, Castelnuovo is a designated Città Slow for this reason. Beyond this former stronghold are a cluster of minor villas and wine estates. Essentially, treat Castelnuovo as a stepping stone to Siena and the southern Chianti.

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Monteriggioni

Spectacular Monteriggioni, north of Siena, is a medieval stronghold, encircled by well-preserved stone walls and fourteen towers. Like Montepulciano, this small hilltop town is emblematic of the Tuscan landscape. Often dubbed `the gateway to the Middle Ages,’ the walled outpost of Monteriggioni is the quintessential medieval town, bristling with fortifications. The hilltop town was built by the Sienese in the thirteenth century to protect their front line from their eternal rivals, the Florentines. Monteriggioni also grew wealthy as a strategic stop along the Via Francigena pilgrimage route. In terms of size and modern-day status, Monteriggioni feels more like a forgotten backwater. It is only when the popular summer medieval festival comes to town that Monteriggioni recalls its past importance, complete with feasting, falconry, jousting and battle re-enactments. Beyond the theatricality of the setting, there are few significant sights but a visit is worthwhile for the magical mood and monumentality alone.

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Pianella

Pianella is a small village that is part of the municipality of Castelnuovo Berardenga. It's a rather modern village but only 15km from Siena and on the edge of the Chianti. It's a perfect village to be near on any self-catering holiday as has all necessities.

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Poggibonsi

Although not the prettiest of the Tuscan towns, Poggibonsi a small historical centre which is nice to walk around if in the town for lunch or to do some shopping. This is a working town with many small industries around it which provide it with a wide range of amenities making it the perfect town to visit for a first stop when stocking up for a self-catering holiday.

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Siena

This compact, pink-tinged city is a delight to discover on foot, from the shell-shaped Campo to the galleries full of soft-eyed Sienese madonnas. Siena is a Gothic city built on a human scale, and is effortlessly civilized and at ease with itself. Where monumental Florence has large squares and masculine statues, Siena has hidden gardens and moody wells. Siena has also made a virtue of conservatism; stringent medieval building regulations protect the fabric of the city.

In keeping with Sienese mystique, the city’s origins are shrouded in myths of wolves and martyred saints. The ancient republic flourished from 1147 until 1529, and shortly afterwards, Siena became part of the Tuscan dukedom. Change is anathema to the Sienese and the citizens are never more themselves than when celebrating the legendary Palio horse race. Still today, Siena’s tumultuous history as arch-rivals of Florence resonates in the souls of the Sienese, particularly during the Palio.

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Vagliagli

South of Castellina lies the scenic hamlet of Vagliagli, perfectly placed for the southern end of the Chianti wine route. This once fortified outpost is surrounded by beguiling wine estates that also date back to medieval times. The sleepy 13th-century hamlet is named after the `valley of garlic’ it surveys, with today’s views more of valleys and hilltops. Admire the handsome, stone-built village and parish church before setting off on a hiking trail, cycle ride or a picnic in the vineyards. The wine-tasting experience may be central to Valgliagli but the hamlet is also a stepping stone to the Chianti strongholds of Castellina, Radda and Gaiole. These beacons of small-town Chianti life are awash with temping wine and food shops linked to local estates. Together, this trio of tiny towns offer enough culture to make a change from estate-visiting. From medieval churches to small archaeological collections, it’s Tuscany in miniature.

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