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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.

    Explore our collection of villas near Castellina.

  • Top Ten Things To Do

    Even if Castellina itself is a key attraction on the Chiantigiana, the Chianti Way also leads to forays to neighbouring Chianti wine hamlets, as well as to San Gimignano, Siena and Florence. Castellina makes a great base for activities as varied as cycling and museum-visiting, wine-tasting and ice cream-slurping. Sample a cookery course or visit a sculpture park: Castellina has it covered.

    This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings.

  • 1. Eat experimental ice cream – Gelateria Castellina

    Experimentation with curious flavours is the way to foodies’ hearts in the region’s best ice-cream shop. Gelateria Castellina is run by Simone, a passionate foodie with a creative touch. For over twenty years Simone has been making ice-cream, pasteurising, churning and blast freezing, with interested onlookers watching him concoct the day’s ices in his show kitchen. The welcome by Simone and Chiara is the friendliest ever. The couple also make semifreddi cold desserts or semi-frozen ice cream cakes. As for the ice cream, flavours range from ricotta and fig to chilli and chocolate, raspberry and rosemary, lemon and kiwi fruit, or coffee and dark chocolate. If you prefer water ices, then choose sorbets concocted from lemon and sage or lime and basil. The strangest creation ever was probably the anchovy and spring onion sorbet, which wouldn’t be for all tastes. Simone’s favourite creation? “That would be cantuccini and Vin Santo: almond biscuits with sweet Tuscan wine.” There’s no escaping wine in the Chianti so just give in and eat up.

    After your ice cream, walk off the calories by exploring Castellina’s warren of backstreets. In particular, stroll down via delle Volte, an 800-metre-long stone-vaulted passageway built into the side of the hill. Apparently, this moody alley was created to permit horsemen to do the circuit of the fortress on horseback. Today the arched alley is home to small boutiques and cafes. From the window slits pierced in the outer you can admire the sheer drop and glimpse the Chianti countryside beyond.


    Address: Via IV Novembre 47
    53011
    Castellina in Chianti

    Tel: 0577 741337
    Web: https://www.gelateriadicastellina.com/

  • 2. Etruscan life at Castellina Archaeological Museum

    The former medieval castle is now a fortified town hall hiding this small, Etruscan-centred archaeological museum. Known as the Museo Archeologico del Chianti Senese, the museum focuses on finds unearthed in Sienese Chianti, including from Castellina, Gaiole, Radda and Castelnuovo Berardenga. In particular, the museum displays Etruscan finds from the 7th-century-BC Montecalvario tombs, Castellina’s aristocratic Etruscan burial mound. Admire the newly reconstructed Montecalvario chariot, with its bronze and iron decorated plates. Look at the talismanic treasures placed with the dead for their final journey — objects such as a gold earring or a bronze belt.

    These Etruscan tombs were built nearly 3,000 years ago but the creators can feel very much like ourselves. On view is an amphora decorated with a scene of revellers at a feast. As in the contemporary Chianti, wine plays a significant role. In Etruscan times, wine was a sign of status, and drunk at rituals and ceremonies. Generally, the wine was mixed with honey and spices but, more curiously, there was also a version featuring grated cheese.

    This castle setting is about far more than the Etruscans so you can also explore the fortress, a former stronghold of the Florentine Republic during its century-long war against Siena. End your explorations with the tower-top walkway and sweeping views from medieval Castellina to the Chianti mountains to the east, and San Gimignano and the Colle di Val d’Elsa valley to the west.


    Address: Museo Archeologico del Chianti 
    Piazza del Comune, 17, 53011 Castellina in Chianti SI


    Tel: 0577-742090
    Web: http://www.museoarcheologicochianti.it/

  • 3. Castellina cycling or wine-tasting tour

    Consider a cycle ride if you want more than the familiar wine-tasting experiences. Variants include picnicking in the vineyards or lingering in the Dievole wine estate for lunch or dinner. South of Castellina, around the hamlet of Vagliagli, is 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 Vagliagli, 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
    53019
    Vagliagli
    Castelnuovo Berardenga


    Tel: 0577 322632
    Web: www.dievole.it

  • 4. Castello di Fonterutoli - wine-tasting & fine dining

    Castello di Fonterutoli is 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


    Address: Via Puccini 4
    Localita Fonterutoli,
    53011
    Castellina in Chianti


    Tel: 0577 741125
    Web: www.mazzei.it

  • 5. Ballooning over the Chianti

    If weary of wine estates or in search of romantic memories, consider an amazing balloon ride over the Chianti. This works well for most people, from couples to families. Being on board a hot air balloon should provide a magical new perspective on Tuscany along with great photo opportunities.

    Very probably you will float above the hills of Castellina in Chianti and recognize the tower and the walled medieval fortress. That said, the precise route isn’t decided until the balloon launch as it all depends on the weather, especially the winds. You should be able to admire the highlights of southern Chianti. This might range from Tuscan castles and Renaissance villas to aerial views of San Gimignano and the prettiest Chianti hamlets and wine estates. Certainly, there will be memorable views of silvery olive groves, vineyards and rolling hills. On a clear day, if the balloon flies high enough, you may even glimpse the Mediterranean reflecting the morning sun.

    For more information, consult Chianti Ballooning, the operators.


    Tel: +39 3381462994
    Web: https://chiantiballooning.com/

  • 6. Castello di Ama for contemporary art

    This leading Chianti Classico producer lies east of Castellina as the crow flies, but not as the winding Chianti roads take you. This working wine estate just south of Radda is known for its superb, full-bodied reds. Castello di Ama is not even a castle but a hilltop estate and villa restaurant, doubling as a centre of contemporary art. At first sight it’s yet another traditional borgo, a stone-built hamlet nestling in the Chianti hills. Slowly, it becomes clear that wine, food and contemporary art are all part of the picture. This was the wine estate that entranced the Obamas on their post-presidential tour of Tuscany.

    The wine is master-minded by Tuscan Marco Pallanti, regularly crowned wine-maker of the year, with wines often in the world’s top ten lists. The estate’s San Lorenzo is a Chianti Classico gran selezione DOCG, a category considered the finest expression of its kind. The 80 hectares of vineyards cover different terroirs, from rocky schist to clay and gravel, with another 40 hectares given over to olive groves. The olives end up in the estate’s extra-virgin DOP Chianti Classico olive oil.

    The grounds are home to a world-class collection of contemporary art installations. This ambitious collection, Castello di Ama per l’Arte Contemporanea (Castello di Ama for Contemporary Art). The sculptures respond to the setting, much as the wines do, and are being added to each year. Castello di Ama repurposes original buildings, such as an on-site church and wine cellar, to showcase art installations in a striking way. The art is hard-core contemporary rather than soothingly pastoral.

    The site-specific contemporary art is commissioned from artists of the calibre of Anish Kapoor, Daniel Buren, Louise Bourgeois, Michelangelo Pistoletto, Hiroshi Sugimoto and Lee Ufan. The most engaging and accessible is the show-stopping mirrored installation by Daniel Buren that reflects the rolling hills. A Louise Bourgeois sculpture entitled Topiary is ingeniously hidden beneath a grate in the wine cellar floor and depicts a female form flowering into a male phallus.  Aima, a thought-provoking Anish Kapoor light installation, illuminates the estate’s tiny chapel.

    Book a wine tour and tasting, come for lunch, visit the sculpture park, or simply visit the estate’s Enoteca to sample and buy the wines, olive oil and nature-inspired home fragrances.


    Address: Castello di Ama
    Localita ama
    53013 - Gailoe in Chianti


    Tel: +39 0577 746069
    Web: https://www.castellodiama.com/en/

  • 7. San Gimignano – medieval Manhattan

    San Gimignano is only 31 km west of Castellina so makes a worthwhile trip to see one of the medieval wonders of Tuscany. Given its spectacular setting, San Gimignano is one of the most touristy towns in Tuscany but manages to rise above the masses. With its moody medieval towers and walls, San Gimignano is one of the symbols of Tuscany. Building a lofty tower-house represented one-upmanship, medieval-style. The tower-studded skyline is one of the most spectacular sights in Tuscany. In its heyday, the city had a total of 72 towers, only 14 of which remain. Tower-houses were castle-residences serving as both warehouses and fortresses. A plague in 1348 wiped out much of the local population and the town slumbered as a backwater for centuries. The result is a medieval time capsule, even if the town is far from slumbering today. Its over-popularity and sometimes inflated prices are the only downsides but shouldn’t deter you from joining the throng.

    See our full San Gimignano guide for more.

  • 8. Rocca delle Macie wine-tasting or cookery course

    Set around 6 km south of Castellina, this stellar wine estate was a tumbledown farmstead until being revitalised by spaghetti western film producer Italo Zingarelli in 1973. The Rocca delle Macie 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 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, come back for dinner at Ristorante Riserva di Fizzano, the estate’s restaurant. 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: Localita Le Macìe
    53011
    Castellina in Chianti


    Tel: 0577 7371
    Web: www.roccadellemacie.com

  • 9. Day trip to Siena

    Siena is a mere thirty-minute drive from Castellina so makes a magical day trip. Siena frames the southern end of the Chianti and so is far more convenient for Castellina. 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.

    Check our Siena guide to see what appeals most.

  • 10. Art-filled Florence

    Florence is only an hour’s drive from Castellina so still makes a perfect outing. Despite devouring the checklist of must-see sights, steer clear of suffocating under the weight of treasures. Allow time for aimless wandering. Beyond the selfie sticks and statuary awaits a funky foodie haunt with sleek cafes, superb cooking and seriously edible markets. Florence is not fusty. Nor has the greedy city lost its gutsy Tuscan soul: traditional inns still serve earthy peasant fare, including macho steaks. Beware of trying to do too much on a day trip. Balance visits to galleries with wanderings in search of the perfect trattoria or the perfect view.

    Check our Florence guide to see what appeals most.

    If visiting a number of museums, consider buying a Firenze Card online (www.firenzecard.it) and also book a time slot at the Uffizi Gallery.


    Web: www.firenzecard.it

  • Eating & Drinking

    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, depicted by famous artist Giorgio Vasari on the ceiling of the Salone dei Cinquecento at Palazzo Vecchio in Florence. Our recommended wine estates are featured in each of the individual Chianti guides.

    As a foodie hotspot, Castellina is peppered with outstanding restaurants, along with appealing food and wine shops. In particular, the ice cream in Gelateria di Castellina is considered the best in the area. Along with a highly traditional attitude to food, the area also offers distinctive delicacies and seasonal dishes, such as truffles and wild mushrooms.

    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.

  • La Taverna Squarcialupi

    Set in a vaulted palazzo in the heart of Castellina, 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
    53011 Castellina in Chianti (SI)
    Tel: +39 0577 741405
    Web: https://www.tavernasquarcialupi.it/

  • L’Antica Trattoria alla Torre

    Set on the main square in Castellina, this old-fashioned, family-style inn boasts a summery terrace. An extensive, mid-priced menu of classic Tuscan fare features the likes of Florentine T-bone steak, grilled meats, or stuffed rabbit, mostly washed down with Chianti Classico wines. Also on offer are pappa al pomodoro, thick tomato soup, mushroom risotto, along with pappardelle alla cacciagione, pasta with game, and a selection of Pecorino cheeses.


    Address: Piazza del Comune 15
    53011
    Castellina in Chianti
    Tel: 0577 740236
    Web: www.anticatrattorialatorre.com

  • L’Osteria di Fonterutoli

    Set in a stone-built farmhouse overlooking the Chianti hills, just south of Castellina, this is an upmarket gastro inn belonging to the Mazzei wine dynasty. The cooking is Tuscan with a contemporary touch, paired with Mazzei wines, especially those from the Castello di Fonterutoli estates. Chef Lorenzo Baldacci’s preference is game, including wild boar stew, along with more novel dishes, such as cheese flan or a pork and olive tapenade. A novel dessert includes the orange, vanilla and cocoa semifreddo.


    Address: Via Puccini 4
    Localita Fonterutoli
    53011
    Castellina in Chianti
    Tel: 0577 741125
    Web: www.mazzei.it

  • Ristorante Riserva di Fizzano

    Nestled among the vineyards just southwest of Castellina, this picturesque hilltop restaurant is decked out in rustic-elegant style. Chef Maurizio Bardotti favours contemporary reinterpretations of Tuscan cooking using seasonal produce. This mid-priced spot belongs to the wine-producing Zingarelli family so expect their estate wines, olive oil and vegetables. Dishes are authentic but sophisticated versions of classics such as Florentine tripe, pork in chestnut sauce, pappardelle pasta in wild boar sauce or tagliolini pasta with truffles.



    Address: Riserva di Fizzano
    Localita Fizzano
    53011
    Castellina in Chianti
    Tel: 0577 737223
    Web: https://www.riservadifizzano.com/

  • La Taverna di Vagliagli

    Just south of Castellina is the medieval hamlet of Vagliagli and a renowned local restaurant. 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 part of the Eroica vintage bike race in October.


    Address: Via del Sergente 4
    Vagliagli
    53019
    Castelnuovo Berardenga
    Tel: 0577 322532

  • Shopping

    Shopping in Castellina is essentially about good-quality Tuscan food and wine, including edible souvenirs. The ice cream in Gelateria di Castellina is considered the best in the area. Some foodstuffs are so delicious that they might never find their way back home. Stock up on Chianti Classico wines, artisanal honey, bottled sauces and dried pasta. For more shopping options, ranging from ceramics to cashmere at a goat farm, visit neighbouring Radda.

  • Enoteca Le Volte

    This wine shop sells wines from some of the most prestigious Tuscan estates, from Antinori and Castello di Ama to Banfi, Barone Ricasoli and Mazzei. Bizarrely, the wine shop also doubles as an ice cream parlour, probably the best in town.


    Address: Via Ferruccio 12
    53011
    Castellina in Chianti
    Tel: 0577 740308
    Web: www.enotecalevolte.com

  • Grocery shopping: Coop supermercato

    This is a small but reasonably well stocked supermarket. Although normally open from Monday to Saturday, it does open on on some Sundays in summer. Check online.


    Address: Via Trento e Trieste 25
    53011
    Castellina in Chianti

  • Enoteca Rocca delle Macìe

    Set within the main Rocca delle Macie Chianti estate, this is a good starting point for visiting the cellars and doing a tasting (Chianti Classico or Super Tuscan versions).


    Address: Localita Le Macìe
    53011
    Castellina in Chianti
    Tel: 0577 732236
    Web: www.roccadellemacie.com

  • Enoteca Castellina in Chianti

    This wine shop belongs to the best-selling Rocca delle Macie Chianti estates and is a showcase for their wines. Consider trying them in the neighbouring Tenuta Le Macie estate or at its on-site Enoteca.


    Address: Via IV Novembre 37
    53011
    Castellina in Chianti
    Tel: 0577 740631
    Web: www.roccadellemacie.com

  • 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 from 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
    50066
    Leccio Reggello
    Tel: 055 8657775
    Web: www.themall.it

  • Parking

    There is a car park off via IV Novembre, at the southern edge of Castellina. There is another car park on the northern edge of the village, from where you can quickly reach the centro storico, the historic centre, with views of Castellina along the ridge of the hill as you approach. Parking is harder to find on Saturday morning, during the weekly market.

    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.

    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

    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 Panzano until you reach Castellina. It is about 20 km from Greve. Or take the Florence-Siena Raccordo Autostradale highway (known as the RA) taking the San Donato in Poggio exit, and then follow the SP101, which becomes the SP76.

    From Siena, leave town on the Florence-Siena Raccordo Autostradale highway (known as the RA), taking the Badesse exit for the SP 119, which becomes the SR222, the Chiantigiana. Or leave Siena and take the SR2, which becomes the SR222 until Castellina in Chianti.

    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
    Web: www.chiantitaxi.com

    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 & www.acvbus.it) 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 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
    Web: www.tiemmespa.it

    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.

  • Tuscan Villas near Castellina in Chianti

    Discover unparalleled beauty from our villa collection near Castellina in Chianti, where Tuscany's allure comes to life. Embraced by the enchanting landscapes, these handpicked villas offer a haven of tranquillity and sophistication. Located in a region steeped in history and culinary excellence, you will not be short of new activities. From savouring the world-renowned Chianti wines to wandering through the cobblestone streets of this historic town, every moment is a celebration of Tuscan culture. Our carefully selected collection of villas, varying in size and amenities, ensures an authentic yet comfortable experience.

    Explore our Siena and Chianti villas to start planning your Tuscan holiday today.

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