Villas in the Chianti

The Chianti

Read our guide to the Chianti

The pleasure of roaming the Chianti is discovering a great winery or crenellated castle all on your own, but you might be interested in some tips: the following towns are all considered Chianti D.O.C. You will encounter them on a meandering circuit that heads northwest out of Siena on the Chiantigiana (SS222). Many of these villages merit a stop and almost everywhere you will find a good place to sample the wine or have a bite to go with it.

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italy > tuscany > florence


Sleeps: 12
€ 2851 - € 5067 per week.

italy > tuscany > siena


Sleeps: 10
€ 3835 - € 6450 per week.

italy > tuscany > siena


Sleeps: 9
€ 2835 - € 4305 per week.

italy > tuscany > siena


Sleeps: 14
€ 2560 - € 3990 per week.

italy > tuscany > siena


Sleeps: 8
€ 3178 - € 4540 per week.

italy > tuscany > arezzo


Sleeps: 18
€ 8000 - € 10105 per week.

italy > tuscany > siena


Sleeps: 6
€ 1038 - € 1851 per week.

Our guide to the Chianti

The Chianti
Historical Notes
Local Events
Things to Do
Towns and Sites
Food and Wine
Market Days

The Chianti

Vendemmia Chianti is an area of about 300 square kilometres of pure Tuscany, right in the centre between Siena and Florence. Entirely hilly, it varies in aspect from the severe and harsh to the sweet and soft, covered in serried rows of vines, green forests or stony meadowland with olive groves and sparse oak trees. The light is really astounding – no view ever seems to be the same from one hour to the next. On clear days you can seemingly see forever; on misty days the light filters the colours and the objects as though through a smoky silk veil, and one seems to be living in a Renaissance landscape.

Chianti Interspersed with the countryside are castles: some are still occupied by the noble families whose ancestors built them in the feudal middle ages; others – ruined, perhaps in battle centuries ago, and abandoned – still dominate their hilltops with proud arrogance. There are numerous hill towns and hamlets, villas and farmhouses, guarded by sentinel cypresses, by people who may make their living tending the vineyards, or have already made more than a living and have retired to beautiful old houses. Jealously protected by the Fine Arts Commission, Chianti is unspoilt and will remain so, but it has such an active agricultural and viticultural life that there is no danger of its sinking into a museum-like tourist attraction.

Historical Notes

Events in the Chianti

Radda 1527 in Radda in Chianti - early July

Radda 1527

Fiera del Cocomero in Castellina in Chianti - 24 August

Fiera del Cocomero

Festa del Giaggiolo in San Polo in Chianti - 1st week of May

Festa del Giaggiolo

Ecomarathon from Castelnuovo Berardenga - mid October


Infiorata del Corpus Domini in San Donato in Poggio - 1st Sunday of June


Festa della Stagion Bona in Panzano in Chianti - 25 April

Stagion Bona

Chianti Classico Expo in Greve in Chianti - early September

Expo in Greve

Sagra delle Fritelle in Montefioralle near Greve in Chianti - 19 March

Sagra delle Fritelle

Chianti Festival in many Chianti villages - 1st & 2nd weekends in July

Chianti Festival

Calici di Stelle in Greve in Chianti, San Casciano & Tavarnelle - 10 August

Calici di Stelle

Vino al Vino in Panzano in Chianti - 17-20 September

Vino al Vino

Festa dell'Uva in Impruneta - last Sunday in September

Festa dell'Uva Impruneta’s autumnal grape celebration of the bounty of its vineyards fills its streets with allegorical wagons and the piazza with merriment. Events begin early in September: the four districts (rioni) of the town, represented throughout the year by flags prominently displayed, compete in a culinary contest to determine which neighborhood makes the best peposo, Impruneta’s signature peppery beef stew, known as its signature dish. The stew was traditionally prepared by brickmakers in a terracotta pot, put into a kiln to slowly cook all morning. The events continue over the weekend, with concerts, carnival floats and more food and of course, plenty of wine.

Eroica Bike Race in Gaiole in Chianti - 4 October 2020


Things to do in the Chianti

Ballooning over Chianti Fly over the Chianti landscape in a balloon You will fly over the legendary Chianti landscape with its hilltop towns, castles, valleys, famous vineyards, and mixed woodlands. A powerful landscape, one of the most civilised rural scenes on earth, cultivated tranquility of olives, vines, and corn. The olives’ silver and the many variegated shades of green appear as a veil over elemental majesty and silence. After landing the balloon is loaded back onto the retrieving vehicles trailer which follows the balloon throughout the flight. Once the balloon is packed away guests are treated to a breakfast with local produce.

Monte Calvario Listen to the ancient stones talk in Castellina in Chianti Castellina in Chianti is located on the Chiantigiana (SS 222) and its Etruscan origins and aristocratic medieval history can be read in what lies below and above the ground. Just outside Castellina, under a tumulus on Monte Calvario, is a four-chambered Etruscan tomb dating from the 6th Cent., discovered a millennium later and excavated in 1915. A fascinating introduction to a pre-Roman civilization.

Sketching Montefioralle Bring a sketch book or camera to Montefioralle o There are many medieval towns perched atop hills in the Chianti, but perhaps for its small-is-beautiful proportion, the ancient circular walls and stunning position, Montefioralle is a treat to visit. Park your car where indicated and walk in to enjoy a virtually car-free hamlet, a friendly restaurant and endless panoramas. And, if you spot a doorway with a wasp (Vespa) sculpted into the top of the arch, you are standing at the ancestral home of Amerigo Vespucci, the famous explorer/cartographer who proved that Brazil was, in fact, not part of Asia and whose name, transformed, became ‘America’. Before you go, read a bit of history of Montefioralle to learn something about this gem of a village.

Biking in Chianti Bike the hills of the Chianti The gently rolling hills of the Chianti region are a biker’s paradise. A land which has remained intact for centuries, it is blessed with extraordinary natural beauty and bathed with mutable light. One cycles through oak and chestnut woods, past carefully tended vineyards and olive groves and spots the hilltop villages, Romanesque churches and scattered villas approached by stalwart cypresses and your know you are in Tuscany. Your Invitation to Tuscany agent can help you rent a bike, have it delivered to your villa and even suggest routes you might take.

Chianti Sculpture Park Take the children to discover sculpture It’s never too early to foster art appreciation and what better way than coming across a surprising work of art while exploring a bit of Chianti woodlands. The Chianti Sculpture Park, open daily from 10 a.m. to sunset, features an eclectic collection of sculptures from 26 international artists. Colorful, curious, and sometimes interactive, the works vary in material and provenance, but are always a delight to discover. An adjacent gallery and summer concerts every Tuesday make this a charming stop for the whole family.

Go wine-tasting and discover a new Chianti favourite

Wine tasting

Towns & Sites

Radda in Chianti

Radda Radda in Chianti Radda is a village of vineyards and the unofficial capital of the Chianti. Its wealth is seen in its many 15th & 16th century palaces which rise amid the medieval buildings. From the Piazza Ferrucci, in which are located the Palazzo Pretorio and Romanesque church of San Niccolò, to the circuit of its fortified walls and the cultivated landscape beyond, it is obvious that Radda knew its livelihood was wed to agriculture. This area appreciates its artists, be they the ancient ones whose gold smithing and stained glass can be admired in the Romanesque church of Santa Maria Novella, dating back to the year 1000, or the fanciful modern sculptures peeking out of the woods in the Parco Sculture del Chianti in nearby Pievasciata.

Castellina in Chianti

Castellina Leaning on a hillside that is a watershed of the three rivers that greatly influenced the history of this area, the Arbia, the Pesa and the Elsa, Castellina has Etruscan origins and an aristocratic medieval history, still seen in the patrician homes and ancient Rocca fortress commissioned by Lorenzo de Medici to protect the city. Via delle Volte, a tunnel running beneath Renaissance dwellings, affords breathtaking views of the Chianti out of tiny openings in the tunnel walls, which originally served the purpose of defence rather than tourism.

Gaiole in Chianti

Gaiole Unlike the other important Chianti centres founded for defence, Gaiole in Chianti has always been a centre of commerce. Markets have been here for centuries, from the early ones that served the nearby castles, to modern local ones that are still held every week like clockwork. Currently Gaiole is famous for its production of cold meats from the Cinta Senese pig, but there are numerous other precious foodstuffs to tempt the visitor.

Greve in Chianti


Panzano in Chianti


Castelnuovo Berardenga

Castelnuovo Berardenga Castelvuovo Berardenga sits at the edge of Chianti Classico territory, but it is still well within the bounds of the Sienese Chianti. At nearby Montaperti Siena enjoyed its moment of glory in 1260 when it drubbed the Florentines; the victors planned to strengthen its outpost with new fortification (hence the name), but finances found their way to other projects and Castelnuovo continued its development into the peaceful prosperous town it is today. Of note is the elegant Villa Chigi Saracini, with its harmonious garden all’Italiana, commissioned by the Count who founded Siena’s Accademia Chigiana di Siena, one of Italy’s foremost musical institutions.

Badia a Passignano

Badia a Passignano

Barberino Val d'Elsa


San Casciano in Val di Pesa

San Casciano



Food and Wine

Finocchiona Antipasti in the Chianti are generous and frequently feature the cured meats and seasoned cheeses produced locally. Expect platters of Affettati, cold cuts that could include prosciutto, salami from Sienese Cinta pig or wild boar, Finocchiona, flavoured with fennel seeds, Soppressata, made of pork trimmings, Bresaola, a cured beef fillet and Lardo di Colonnata, cured and herbed lard, to name a few. Local cheeses tend to be Marzolino and Pecorino (sheep), in various stages of aging and accompanied by honey, marmalade or mostarda, a cooked fruit marinated in spicy, mustard oil-flavored syrup

Schiacciata d'Uva The past traditions and economy of the sharecroppers who tended this land still influence its diet. The bread, once baked in a wood-burning oven and still often unsalted to accompany the flavorful Tuscan sauces is never thrown away. Any leftovers find their way into salads and soups such as Panzanella, Ribollita, and Pappa col pomodoro.

Pappardelle Pasta courses utilize the delicious ingredients found in this part of Tuscany, including the vegetarian-friendly Tartufi, truffles, Zafferano saffron, Carciofi artichokes or Porcini mushrooms. For meat-eaters options are endless and a speciality of this area are the Pappardelle whose wide noodles pick up the hearty sauces accompanying wild boar, hare or poultry.

Stracotto The wine for which the region is known also finds its way into the Chianti cuisine, enhancing sauces and contributing to the tender taste of Stracotto typical Chianti braised beef. The menu is vast and varied: beef and veal, pork from the Cinta Senese and wild boar, chicken, pheasant, duck and goose, rabbit, doves and pigeons, with lamb always at Easter.

Fritelle Dessert may often include Crostata, a fruit tart, or a Pinolata, pine-nut and cream cake, and very often VinSanto in which to dip your Cantucci biscuits.


Market days

MONDAYS –San Casciano Val di Pesa, Gaiole in Chianti (2th of month), Radda (4th)

TUESDAYS – Strada in Chianti

WEDNESDAYS – Impruneta, Barberino Val d’Elsa, Siena

THURSDAYS –Tavarnelle Val di Pesa, San Polo in Chianti, Castellina in Chianti, Castelnuovo Berardenga

FRIDAYS – San Donato in Poggio

SATURDAYS – Greve in Chianti, Castellina in Chianti, Barberino Val d’Elsa, Impruneta

SUNDAYS – Panzano in Chianti


Badia a Coltibuona, - near Gaiole in Chianti, Tel +39 0577 74481
La Bottega del Moro - Greve in Chianti, Tel +39 055 853753
Antica Trattoria La Torre - Castellina in Chianti, Tel +39 0577 740236
Sotto Le Volte - Castellina in Chianti, Tel +39 0577 741299
Solociccia - Panzano in Chianti, Tel +39 055 852727
Bottega di Volpaia – Volpaia, Tel +39 0577 738001
Perla del Palazzo - Radda in Chianti, Tel +39 0577 735640
La Sosta del Papa– near Barberino Val d’Elsa, Tel +39 055-8075626
Le Forchette del Chianti – Radda in Chianti, Tel +39 0577 738923
Da Antonio – Castelnuovo Berardenga, Tel +39 0577 388321
La Castellana – Montefioralle, Tel +39 055 853134
Cantinetta del Nonno – San Casciano in Val di Pesa, Tel +39 055 820570
Osteria Bottega di Lornano – Lornano, Tel +39 0577 309146
Locanda di Pietracupa – near San Donato in Poggio, Tel +39 055 8072400
Ristoro di Lamole – Lamole, Tel +39 055 8547050