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  • 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.

  • 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 outposts, all accessed through our Destinations listings, For starters, check out our guides to Greve, Panzano, Castellina, Radda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San Gusme, San Donato in Poggio and Vagliagli.

  • 1. 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.

    Address: Dievole, Località Dievole 6,
    Castelnuovo Berardenga
    Tel: 0577 322613 / 0577 322632

  • 2. 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
    Castellina in Chianti
    T: (+39) 347 679075 & 0577 742090

    Gelateria Castellina
    Via IV Novembre 47
    Castellina in Chianti
    T: 0577 741337

    L’Antica Trattoria alla Torre
    Piazza del Comune 15
    Castellina in Chianti
    Tel: 0577 740236

  • 3. 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.

    Address: Chianti Sculpture Park (Parco Sculture del Chianti)
    Localita la Fornace 48
    Tel: 0577 357151

  • 4. 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

    Address: L’Osteria di Fonterutoli
    Via Puccini 4
    Localita Fonterutoli
    Castellina in Chianti
    Tel: 0577 741125

  • 5. 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.

    Address: Rocca delle Macie
    Localita Le Macìe
    Castellina in Chianti
    Tel: 0577 7322367321 / 0577 737223

  • 6. Day trip to 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.

    Address: Siena Tourist Office
    Spedale di Santa Maria della Scala
    Piazza Duomo
    Tel: 0577 280551

  • Eating and Drinking

    In rural Chianti, food and wine are the real religion. Our recommended local wine estates with restaurants include Dievole, Castello di Ama, Casanuova di Ama, Rocca delle Macie, Fonterutoli and Castello di Selvole, all featured in this guide. For other estates, do see our individual Chianti guides.

    The local Chianti cuisine is as traditional as the castle-strewn countryside. Rustic ribollita soup, often made with black cabbage and beans, is on the menu. Not for nothing are Tuscans derided as `bean-eaters’ by grander culinary rivals. Typical dishes include ribbons of pappardelle pasta in a meaty wild boar sauce or a massive T-bone steak, bistecca alla fiorentina.

    This is just a taster to the Chianti. See our restaurant recommendations below and also see our other guides to top Chianti towns and villages, all accessed through our Destinations listings, In particular, see our guides to Lecchi in Chianti, Radda in Chianti and Castellina in Chianti, which are all nearby.

  • Taverna di Vagliagli

    Although not cheap, this friendly, traditional inn is far better value than comparable restaurants in neighbouring Siena. Locals consider it every bit as good, particularly for grilled meats and pasta. Chef Andrea concocts typical Tuscan dishes, such as hearty ribollita soup, fried courgettes, tagliatelle or ravioli with meaty ragù sauce, and his signature Florentine style T-bone steak. This mid-priced rustic-elegant restaurant opens onto a pleasant summer terrace. This is the spot from which to view the October L’Eroica vintage bike race,

    Address: Via del Sergente 4
    Castelnuovo Berardenga
    Tel: 0577 322532

  • Il Ristorante Malborghetto

    This much-loved, mid-priced inn is highly-rated by both the locals and visitors. Tuck into their vegetarian-friendly antipasti, including herbs and vegetables from the chef’s kitchen gardens. Typical dishes include Pecorino and pear tortellini, truffled gnocchi, stewed rabbit, wild boar stew, and panna cotta. Book ahead and request a table on the terrace in fine weather. If impressed by dinner do the cookery course with chef Simone Murici, including Chianti Classico wine-pairing. Learn how to make a complete meal, featuring such dishes as ravioli, steak, ragu sauce, truffle dishes and tiramisu. The morning course ends with you eating your feast. The cookery course costs around €135 per person. This village inn is set in Lecchi in Chianti about 5 km off the SS408 Gaiole-Siena road.

    Address: Via Monteluco 4
    Localita Lecchi in Chianti
    Gaiole in Chianti
    Tel: 0577 746201

  • La Taverna Squarcialupi

    Set in a vaulted palazzo in the heart of Castellina in Chianti, this big, bustling taverna (tavern) showcases pasta dishes along with the wines and olive oil from the local Fattoria la Castellina. Expect a mix of modern Tuscan and inventive Italian cooking with such tweaks as serving wild boar in a chocolate sauce. Try the duck in Chianti sauce, the pumpkin risotto or the chick-pea flour cannelloni with truffle sauce. Enjoy wine pairings if wished in this mid-priced inn. Sit on the sunny terrace built into the medieval town walls and drink it all in.

    Address: Via Ferruccio 26
    Castellina in Chianti
    Tel: 0577 741405

  • Shopping

    Shopping in Vagliagli is very limited so for more varied shopping options, head to neighbouring Castellina, Radda, Gaiole and, best of all, Siena. Castellina and Radda both have decent supermarkets and are awash with quirky Chianti Classico wine shops. As a change from wine lakes, Radda is also the place for browsing for Tuscan ceramics or cashmere.

  • Alimentari Rovai

    This small grocery shop in the centre of Vagliagli is stocked with all the basic items, including fruit and vegetables, plus a choice of local cheeses and cured meats. It’s a handy place to pick up drinks and panini for a snack or lunch on the run.

    For substantial grocery shopping head to the Coop Castellina supermarket (via Trento e Trieste 36, Castellina) or the Coop Radda supermarket (Via Primo Maggio 32, Radda). Both Chianti centres are around a 7 km-drive from Vagliagli. Castellina, in particular, has plenty of specialised food and wine shops.

    Day closed: Sunday

    Address: Piazza Vittorio Emanuele 10
    Castelnuovo Berardenga
    Tel: 0577 322622

  • Dievole

    This welcoming wine estate south of Lecchi is the place to stock up on good wine and olive oil.

    Address: Località Dievole 6
    Castelnuovo Berardenga
    Tel: 0577 322613 & 0577 322632

  • Il Castello di Selvole

    Call into the local wine estate, Castello di Selvole, to buy Chianti Classico wines, as well as Merlot and Cabernet Franc. Consider booking dinner at L’Osteria La Botte, the estate restaurant.

    Address: Localita Selvole
    Castelnuovo Beradenga
    Tel: 0577 322662 & 0577 1912577

  • L’Azienda Agricola Casanuova di Ama

    This small, family-run wine estate in the hamlet of Casanuova di Ama near Lecchi offers wine-tastings, along with sales of Chianti wines, Super Tuscans, Vin Santo, grappa and olive oil. Daniela, the owner, does brief tours, perhaps followed by a vegetarian-friendly lunch in the cosy estate inn for home-cooked Tuscan dishes, such as crostini slathered in tomatoes, home-made gnocchi, freshly-baked bread and cantuccini biscuits for dipping in Vin Santo.

    Address: Localita Casanuova di Ama
    Gaiole in Chianti
    Tel: 0577 746119

  • La Fornace

    This gallery is in Pievesciata, beside the Chianti Sculpture Park and is run by the founders and owners of the park, Piero and Rosalba Giadrossi. Set in an old terracotta factory, this gallery displays contemporary sculptures and paintings by Italian and international artists, including emerging artists.

    Address: Localita La Fornace 48/49
    Castelnuovo Berardenga
    Tel: 0577 357151

  • Luxury designer outlets

    For a complete change of scene, designer shopping fans could head to the luxury outlets in the Valdarno area. The Mall Firenze is a thirty-minute drive east of Florence, on the Pontassieve road. There’s also a direct shuttle bus there from Siena. After browsing the designer brands, end your shopping experience in the Mall’s Gucci café and restaurant.

    Address: The Mall,
    Via Europa 8, 5
    Leccio Reggello
    Tel: 055 8657775

  • Parking

    Parking in Vagliagli is rarely an issue. You can park along Strada Provinciale (SP) di Vagliagli/Via del Lago. If visiting Dievole wine estate (Localita Dievole 6,, park there.
    Note that most Tuscan towns operate a strict ZTL system, a Limited Traffic Zone. This means that the Centro Storico (historic centre) is essentially closed to traffic, particularly for non-residents. Cars will need to be left outside the walls. That said, the Chianti towns are small so present far less trouble than such cities as Florence and Siena. Parking tips: for advice on individual Chianti places, please see our individual Destination guides, including those on Greve, Panzano, Castellina, Radda, Gaiole and Castelnuovo Beradenga.

    Advice on ZTLs: You may see other cars crossing the ZTL boundary (Limited Traffic Zone) and assume you can proceed. Not so. The drivers crossing into the ZTL zone will probably be locals and have residents’ permits. Visitors do not so are liable to fines. Zones are monitored by cameras, so tickets are issued immediately and automatically, as soon as (and each time) the car crosses the ZTL boundary.

  • Getting Around

    Vagliagli lies 15 km north of Siena and 75 km south of Florence so is best situated for exploring the southern Chianti and, of course, Siena and towns south, including Rapolano.

    The Chianti can be delightful driving country. Its appeal lies in the rolling countryside, array of vineyards and olive groves, relatively quiet roads, and the mix of small medieval towns. Public transport in the Chianti is rather sporadic so car hire makes the most sense if you want to explore the area properly. Driving in the Chianti can be deeply enjoyable experience, especially with a detailed map or GPS navigator to hand. For a great day out, try a customised tour with Chianti Taxi.

    Greve, the main gateway from the north, lies on the SR222, commonly known as the Chiantigiana, about 30 km south of Florence and 40 km north of Siena. From Greve, the scenic Chiantigiana meanders through the Chianti, passing through most of the typical villages. This is a charming route to take by day. At night, however, you might encounter wild boars, porcupines or deer crossing the road.

    From Florence and the Chiantigiana head towards Greve, then further south to Radda and Gaiole.  Or pick up the Florence-Siena Raccordo Autostradale highway (known as the RA) and take the San Donato in Poggio exit before following the SP101, which becomes the SP76.

    From Siena, leave town on the fast Florence-Siena Raccordo Autostradale highway (known as the RA), taking the Badesse exit for the SP 119, which becomes the SR222, the Chiantigiana. Or take the quieter, slower route from Siena: take the SR2, which becomes the more tranquil SR222 until Castellina and then onto Radda and Gaiole.

    The Chianti by train
    This is not an easy place to reach by rail. The train service barely touches Chianti's attractions, which is part of the reason why the area is so peaceful. The main Chianti station is Castellina in Chianti, which is on the Siena-Florence line but you need to change trains at Empoli.

    The Chianti by bus:
    Buses connect Florence to Greve and Panzano but end there. These buses often provide a more useful service than the trains but the confusing 365 bus service (T: 800373760, freephone only & still means that bus schedules are not always convenient and also operate a limited service on Sunday. Buses also connect Siena and Castellina: a Tiemme bus service (T: 0577 204111 & operates around 7 services a day.  Buses also connect Castellina and Radda: a Tiemme bus service Buses also connect Siena and Gaiole.

    Tel: 0577 204111

    On your bike:
    The Chianti is a lovely place to explore by bike. The combination of romantic Tuscan scenery and challenging gravel roads is what makes it enjoyable. The cycling races in the region also attract big crowds. Whether as a spectator or a participant, L’Eroica is worth following. This renowned amateur event that allows cyclists from around the world to experience the region while riding classic bikes. The parking in Gaiole is outside the town centre on the Strada Provinciale 408 or in the car park on via Marconi. Note that most Tuscan towns operate a strict ZTL system, a Limited Traffic Zone. This means that the Centro Storico (historic centre) is essentially closed to traffic, particularly for non-residents. Cars will need to be left outside the walls. That said, the Chianti towns are small so present far less trouble than such cities as Florence and Siena. Parking tips: for advice on individual Chianti places, please see our individual Destination guides, including those on Greve, Panzano, Castellina, Radda and Castelnuovo Beradenga.

    By private tour:
    Chianti Taxi, a reliable Panzano-based transport service offers day-long private tours around the Chianti and beyond. These are customised tours that can take in everything from olive oil mills and wine estates to Pecorino farms and hand-painted ceramics. With his comfortable minivan, owner Daniele Mogni has the inside track on what you can do in the Chianti. It’s worth splashing out for a day so you can relax and drink your fill at the wine estates.

    Tel: (+39) 389 8160050

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