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Things to do

Vagliagli borders the southern Chianti and so is well-placed for cultural outings to Siena and Castellina in Chianti. Florence and San Gimignano are further away but still make tempting day trips for culture-lovers. Closer to home, it’s all about visiting a sculpture park and indulging in vineyard and wine-tasting tours, fine dining and rustic inns, including in castles. That’s not forgetting cycle rides, Vespa tours and gourmet picnics in the rolling countryside. It’s an outdoorsy lifestyle.

This is just a taster to the Chianti. See our specific guides to top Chianti towns and villages nearby, all accessed through our Destinations listings, For starters, check out our guides to Gaiole, Greve, Panzano, Radda, Castelnuovo Beradenga and the general Chianti guide. Our additional Chianti guides cover Castagnoli, Volpaia, San Donato in Poggio, San Gusmè and Lecchi.

Things to do

Dievole estate cycling, picnicking or wine-tasting tour

Consider a cycle ride or a gourmet picnic in the vineyards around Vagliagli if you want more than a wine-tasting experience. A variety of tempting rural experiences can be booked through the Dievole  estate, which may well end with a candlelit dinner in one of the estate restaurants.

Around the hamlet of Vagliagli lies an appealing cycle route that takes you past rolling vineyards in leisurely fashion. Expect flitting butterflies, trilling birds and the smell of baked earth as you cycle.
The route begins in the hamlet itself, with an intriguing 26 km trail around vine-clad slopes. At its heart is the Dievole wine estate, a 400-hectare property 12 km north of Siena. Although it’s a private estate, anyone is welcome to ride the trail, which has recently been revamped and signposted. The `new’ trail was devised by an estate-worker, who knows the land like the back of his sun-leathered hand. In one sense, the trail is as ancient as the hills and was used by Tuscan sharecroppers for almost a thousand years. Ideally consult the Dievole estate before setting off on the trail and consider booking the gourmet picnic option.

The Dievole 80-hectare wine estate has been cultivated since 1090, when it was a monastic holding. Today, the property also produces award-winning olive oil. From the highest point of the vineyards stretch views of olive groves, deep woods and cascading vineyards planted with the grapes required for Chianti Classico. The estate offers gourmet picnics and cycle tours, as well as wine and olive oil tastings, complete with Pecorino cheese and crostini drizzled with olive oil. If won over by the spot, linger over a romantic gourmet dinner at Ristorante Dievole, or just a light lunch in the same place. The fallback restaurant, Giardino del Tasso, is another recommended spot for a candlelit dinner.

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Castellina in Chianti day out

Visit neighbouring Castellina in Chianti, a charming haunt north-west of Vagliagli. Explore the Archaeological Museum to see finds from Etruscan tombs, including an amphora depicting drinking and feasting, showing that wine was a sign of status, drunk at rituals and ceremonies. Even though the tombs were built nearly 3,000 years ago, the creators can feel very much like ourselves. Climb to the tower-top walkway to enjoy sweeping views over the Chianti mountains, San Gimignano and the Val d’Elsa. Wander down via delle Volte, a quaint stone-vaulted street built into the side of the hill.

Consider your first wine-tasting at an enoteca as Castellina is awash with Chianti Classico. The trademark on bottles of Chianti Classico is the Black Rooster (or Black Cockerel), the historic symbol of the Chianti Military League. In the late 13th century, Castellina was the first site of the Chianti League, a group of three Florentine feudal castles. Call into L’Antica Trattoria alla Torre for lunch. Set on the main square, this old-fashioned inn serves Tuscan treats on a summery terrace. Tuck into the Florentine T-bone steak, grilled meats and Pecorino cheeses, all washed down with Chianti Classico wines, of course.

After lunch, devour delicious ice cream at Gelateria Castellina, known for its experimental ices. The flavours range from ricotta and fig to chilli and chocolate or lemon and kiwi fruit. There’s also the owner’s favourite creation, cantuccini and Vin Santo: almond biscuits with sweet Tuscan wine. There’s no escaping wine in the Chianti. Before leaving, stock up on Tuscan foodstuffs, including cheeses, biscuits and cured meats. (For shopping suggestions, see our guide to Castellina in Chianti
Castellina Archaeological Museum
Piazza del Comune 17
53011
Castellina in Chianti
 T: (+39) 347 679075 & 0577 742090 www.museoarcheologicochianti.com
Gelateria Castellina
Via IV Novembre 47
53011
Castellina in Chianti
T: 0577 741337
www.anticadelizia.it

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Chianti Sculpture Park for an engaging art trail

The Chianti Sculpture Park, set in Pievasciata, south of Vagliagli, makes a refreshing change from eating and drinking your way through the Chianti, lovely though that is. This harmonious Sculpture Park, also known as the Parco Sculture del Chianti, fills a small oak wood and even spills out into the local community. The route there covers a patchwork of olive groves and hills draped in vineyards, with sublime views unfolding around every hairpin bend. Once there, simply follow the wooded trail that winds past sculptures cast in a multitude of materials and styles.

The Sculpture Park is curated by art-dealers Piero and Rosalba Giadrossi, who often help out so you might well meet them. The concept comes from the ancient Italian tradition of creating site-specific artworks for the outdoors. Around 40 contemporary sculptures by different artists are dotted through the woods of this 17-acre site. Along the way, you can spiral through a life-size labyrinth made of glass cubes, and gaze at a sculpted cypress-like sculpture that looks more vivid than the real thing.

Given such a diverse collection, some sculptures will speak to you while others won’t. Most are thought-provoking. Thinker by Ichwan Noor from Indonesia is a homage to Rodin's Thinker but features a workaday character rather than a noble being. Suspended Stone by Mauro Berrettini is ingenious, a light-seeming sculpture made from travertine quarried from Rapolano, south of Siena. Energy, by the Greek sculptor Costas Varotsos, reveals a cypress-like structure perched on a rocky location. Labyrinth, by the British artist Jeff Saward, was inspired by a stone labyrinth in stone found in Val Camonica, Naquane dating back to 700-800 BC. This one is octagonal, not round like the original. In general, the materials used range from true marble and granite sculptures to more modern installations involving neon lights and sound. There’s also a bridge of bright blue tiles that, on clear days, frames the distant skyline of Siena. Some works are now found outside the park so look out for the artily incongruous British red telephone boxes, for instance.

There’s also an amphitheatre in the park for outdoor summer concerts, with genres embarcing classical, opera, jazz, folk, Gospel and tango. Even the amphitheatre is arty, made of slabs of white Carrara marble from Michelangelo's quarry, black granite from Zimbabwe and the stage covered with lava-stone. Definitely pick up an audio guide to the Sculpture Park from the entry kiosk or download the app before you visit.

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Castello di Fonterutoli - wine-tasting & fine dining

About 5 km north-west of Vagliagli is Castello di Fonterutoli, the first significant wine estate south of Castellina, a former Florentine outpost. This 21-hectare estate forms the ancestral heart of the Mazzei land-holdings, which the Mazzei marquesses have owned for 24 generations, ever since 1435. Even though the estate is 6 km south of Castellina, the views extend to Siena. From this timeless stone-built hamlet you can make out Siena’s Torre del Mangia and the outline of Siena Cathedral. These Fonterutoli estates are largely planted with Sangiovese, with a far smaller proportion of Merlot, Malvasia Nera, and Colorino. Fonterutoli’s award-winning Chianti Classico wines are matched by their grappa, olive oil and Tuscan cuisine. If tasting the wine barons’ vintages is not enough, then buy the estate lavender and natural Tuscan beauty products, created by Carla Mazzei, scion of the estate’s great wine dynasty. Stay for lunch or dinner at L’Osteria di Fonterutoli, the estate’s acclaimed restaurant.

The estate is also a pretext to delve into local history as Fonterutoli was, for both the Florentines and the Sienese, a significant battleground. In the early 13th century the warring Republics of Florence and Siena fought over Chianti territory, sandwiched as it was between the two great rivals. To determine fixed borders and end this dispute forever, it was determined that two knights would depart from their respective cities and fix the boundary point at wherever they met. Dawn was the agreed departure, with the signal to ride announced by the rooster’s crowing. The Florentines cheated and won.

Their symbolic black rooster was kept in a dark coop and practically starved so crowed as soon as it was released. The Florentine knight set off immediately and, with this huge head start, met the Sienese knight at Fonterutoli, just 12 km from the gates of Siena. The Sienese white rooster faithfully followed instructions but was vanquished by Florentine trickery. As a result, most of the Chianti was brought under Florentine control, far earlier than the defeat of Siena itself in 1555. A triumphant Florence brought its border to Fonterutoli along a new border marked by Castellina, Radda and Gaiole, and established the Chianti Military League, with the Black Rooster as its shield. History has given the Sienese the last laugh: Castellina, Radda and Gaiole are now Sienese territory once more.
L’Enoteca, Castello di Fonterutoli (wine tastings and tours)
T: 0577 741385
www.mazzei.it

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Rocca delle Macie wine-tasting or cookery course

A charming wine estate-lined route leads west for 13 km via Fonterutoli to Rocca delle Macie. This stellar wine estate was a tumbledown farmstead until revitalised by spaghetti western film producer Italo Zingarelli in 1973. The project fulfilled his lifelong dream of owning vineyards in the heart of Chianti Classico. The estate is now run by Sergio, his youngest son and current head of the Consorzio Vino Chianti Classico, the Chianti Classico Consortium. This young, forward-looking estate produces best-selling wines. The 500-hectare estate is spread over the Castellina and Scansano areas, with four wine estates in the Chianti and a further two in the prized Morellino di Scansano wine area. As well as 200 hectares of vineyards, the estate produces excellent olive oil on its 40 hectares of olive groves.

The 93-hectare Tenuta Le Macie estate, set in the south-west part of the Chianti, forms the heart of the company and occupies the loveliest vineyards. The terraces are mainly planted with Sangiovese grapes, along with some Cabernet Sauvignon, Merlot and Colorino. As well as the prized Chianti Classico wines, you can sample some IGT Super Tuscans. Unlike more inward-looking estates, this one believes in collaborating with others, whether in San Gimignano or Orvieto, to produce particular wines. For a true taste of the region, sample one of the estate’s best Chianti Classico wines, which reveal fruity notes of blackcurrant and cherries. Either do the basic wine-tasting (of Chianti Classico or the Super Tuscans) or opt for the three-hour wine-tasting tour which includes dinner, ending with dessert and Vin Santo.

Alternatively, sample dinner at Ristorante Riserva di Fizzano, the estate’s restaurant, set in their neighbouring estate at Fizzano. If impressed, consider booking a cookery course with Aldo, the resident chef. Typical dishes to master include pici all’aglione, (stubby pasta in garlic sauce), pappa al pomodoro (thick bread and tomato soup) and typical cantuccini almond biscuits.

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Seductive Siena

Siena is a twenty-five minute (15 km) drive south from Vagliagli and makes a magical day trip. As a Gothic city built on a human scale, Siena is effortlessly civilised and at ease with itself. All roads lead to Il Campo, the beguiling, shell-like central square, shaped like an amphitheatre. Sit at a terraced café on the sloping side of the square and spot the division of the paved surface into nine segments, recording the wise Council of Nine who governed Siena from the mid-13th century to the early 14th. Consider climbing the slender Torre del Mangia, with sultry views over a pink piazza and Siena’s rooftops, even if the views from the Cathedral rooftops are even better.

After an early lunch, a leisurely stroll leads to the Duomo, Siena’s pinnacled Gothic cathedral. The facade is a riot of green, pink and white marble, like a glorious iced cake. Siena Cathedral and the Cathedral Museum should be seen as one entity as they share several spaces. The Museum displays Pisano’s original statues for the façade along with Siena’s best-loved work, Duccio’s Maestà, the Virgin Enthroned. For many visitors, equally impressive is the rooftop walk, known as the Panorama from the Unfinished Façade. These are arguably the finest views of Siena. Facing the cathedral is the Spedale di Santa Maria della Scala, the most extraordinary building in Siena. It began as a hospital a thousand years ago and continued as one until it was reborn as a magnificent museum in recent years. In medieval times, it was always far more than a hospital. The art-studded complex embraces a former pilgrims’ hostel, an orphanage, frescoed churches and granaries.

Don’t let Siena’s art-studded museums blind you to the beauty of the backstreets. Here, the city history unfurls like a medieval banner. Walkable Siena has well-preserved walls and inviting gateways. Wind through a tangle of medieval streets and stumble across secret courtyards, fountains and surprisingly rural views. Check our Siena guide to see what appeals most.

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