Chianti holiday guide

Written by Donald Strachan, Italy specialist and Travel Writer for The Guardian.

Art & architecture

The Chianti has been fought over for centuries, most famously between rivals Siena and Florence at the Battle of Montaperti in 1260—the battle site lies between Castelnuovo Berardenga and Siena. In the 12th century the three principal Chianti towns (Castellina, Gaiole, and Radda) formed a defensive alliance, the Chianti League, and took the Black Rooster (the Gallo Nero) as its symbol.

The legacy of that turbulent history remains, in the still-fortified towns Castellina in Chianti and Radda in Chianti, and in a rural landscape dotted with castles.

The Castello di Brolio owes its distinctive, hybrid appearance to centuries spent on the front line: between Florence and Siena, between Tuscany and the Spanish, and between the Allies and retreating German forces during World War II.

Parts of the original structure date to at least the 1000s, and embellishments continued until 19th-century, with additions in the neo-Gothic style. Parts of the castle and its historic Ricasoli wine cellars—where 'modern' Chianti wine was first blended—are open to public view, as part of a guided tour and tasting.

If you just want to taste Castello di Brolio's wine, visit its up-market roadside Enoteca. It stocks the entire range. Tasting usually costs €5 for three wines, which is reimbursed if you buy a bottle or two.

The Chianti's remoteness also attracted monastic orders. Many founded abbeys and retreats hidden away from nearby cities Florence and Siena, as well as from the region's squabbling towns.

The Vallombrosan order founded the Abbazia di San Michele Arcangelo a Passignano in the 11th century on a knoll amid some of the Chianti's prettiest scenery—the order's founder Giovanno Gualberto died here in 1073 and is buried in the abbey. Much altered over the centuries, the abbey refectory has a Last Supper frescoed by the Ghirlandaio brothers. Unfortunately, the interior is usually closed to visitors.

On a smaller scale, the countryside is dotted with hamlets huddled around their pieve, or parish church. Many date from the Romanesque period. The building is often a simple place, time-worn and spiritual. It feels especially atmospheric at San Leolino, which has stood just south of Panzano since at least the 10th century—though the building and interior panel paintings date mostly from between the 12th and the 15th centuries.

The Chianti's painting and sculpture highlights are understated—its small towns and tiny churches were off the radar for first-rate painters from Florence or Siena. In Greve, tiny Santa Croce has a Madonna and Child triptych attributed to Bicci di Lorenzo. The churches handsome façade was designed in neo-Renaissance style in the 1830s, complete with grey pietra serena stone used in Brunelleschi's Florentine buildings.

The exhibits at the Parco Sculture del Chianti are of a more recent vintage. The outdoor sculpture park was set up in seventeen acres of mixed woodland in 2004. Contemporary sculptures were commissioned from all over the world specifically for the site, where visitors can follow a marked footpath.

  • Don't miss

    Wine tasting in fine Chianti cellars

    Enjoying the rustic flavours of Tuscany served on the panoramic terrace at L'Antica Scuderia

    Walking along the street, but underground, on the Via delle Volte at Castellina in Chianti

    Castello di Brolio, just outside San Regolo, tel. 0577/730280, www.ricasoli.it; closed between December and February

    Abbazia di San Michele Arcangelo, Badia a Passignano

    Santa Croce, Piazzetta Santa Croce, Greve in Chianti

    Pieve di San Leolino, Panzano in Chianti

    Parco Sculture del Chianti, Pievasciata, tel. 0577/357151, www.chiantisculpturepark.it; between November and March, call ahead to check the site is open

Eating and drinking

Bring an appetite to the Chianti… because you are going to need it. The produce here is justly famous; this is the spiritual home of la cucina toscana, a 'peasant' cuisine where the ingredients are king. Classic starters include panzanella, a salad of tomatoes, basil, and yesterday's bread soaked in olive oil, and pappa al pomodoro, a thick tomato soup-stew. For the carnivorous, tonno del Chianti (literally, 'Chianti tuna') is seasoned pork cooked and preserved in oil and white wine.

The best pasta is always made fresh and in-house; wide, flat pappardelle come coated in a Tuscan ragù made with wild boar (cinghiale), hare (lepre), or more delicate rabbit (coniglio).

Mains are usually all about the meat, whether a spicy peposo (beef stew with paprika) or a bistecca alla fiorentina (T-bone-like meat on the bone, usually served quite rare, de-boned, and sliced).

Out on the covered sundeck, among the citrus trees and climbing roses, at L'Antica Scuderia: this is one of the Chianti's refined, relaxed dining spots, and you won't feel unwelcome if you arrive in a polo shirt and shorts. The menu mixes rustic Tuscan classics with the likes of risotto with zucchini e zafferano (courgettes and saffron) and carpaccio del Chianti (sliced raw beef with porcini mushrooms and black truffle shavings). There are child-friendly treats, too, including bocconcini dai dai—home-made 'sweets', chocolate-coated ice-cream balls served in individual wrappers.

In Greve, Mangiando Mangiando has a touch of modernity running through its menu. Traditional flavours feature, too, including coniglio ripieno (stuffed rabbit) and pasta with a ragù of Cinta Senese pork. There's also fresh fish daily (brought in from Orbetello, in the coastal Maremma) and main-course salads in summer, including the Caterina de' Medici, with rocket, anchovies, pecorino cheese, and walnuts, which makes a filling lunch for under €10.

The terrace at the Ristoro di Lamole is a memorable spot for a dinner. And there's more than just a pretty view on offer: pastas such as ravioli di pere e pecorino senese (ravioli with pear and sheep's milk cheese) are made in house. The wine list is stuffed with local labels.

Things are a little more informal at Dario DOC—a 'Tuscan fast food' place still often known as MacDario. You can see where it got its nickname: it's all about the meat here, as you might expect from a venture operated by local celebrity butcher Dario Cecchini. Choose between a breaded 'burger', a small medallion of beef, or a tasting plate of carnivorous treats, all with sides. Set menus range €10 to €20 a head, and everything is served at communal benches. They don't accept reservations.

Look out for the bikes propped against the wall to spot the Chianti's best ice-cream parlour, L'Antica Delizia, right by the main Chiantigiana road at Castellina. It's a favourite refueling stop for cyclists.

  • Don't miss

    L'Antica Scuderia, Via di Passignano 17, Badia a Passignano, tel. 055/8071623, www.ristorolanticascuderia.it

    Mangiando Mangiando, Piazza Matteotti 80, Greve in Chianti, tel. 055/8546372, www.mangiandomangiando.it

    Ristoro di Lamole, Lamole, tel. 055/8547050, www.ristorodilamole.it; closed Wednesdays in winter

    Dario DOC, Via XX Luglio 11, Panzano in Chianti, tel. 055/852176, www.dariocecchini.com; open lunchtimes only, closed Sundays

    L'Antica Delizia, Via Fiorentina 4, Castellina in Chianti, tel. 0577/741337, www.anticadelizia.it; closed Tuesdays, and completely between Christmas and early March

Wine tasting

Chianti is one of Italy's great red wines, and has been a favourite of the English (in particular) since the 1600s.

Chianti's main ingredient is the carefully squeezed juice of the Sangiovese grape. However, it is a blended wine, and may also contain up to 20 percent of other red grape varieties, including local varietals Canaiolo and Colorino, as well Merlot or Cabernet Sauvignon. It is this flexibility in the recipe, along with differing rules for 'regular' and aged, riserva wines (24 months minimum in oak), that gives Chianti its surprising diversity.

Remember to look out for Chianti Classico on the label, which guarantees that grapes came from the original and best Chianti growing zone, enshrined in law in 1932. Most Classico growers use the Black Rooster, the Gallo Nero, as a symbol to denote the authenticity and quality of the wine.

Several top Chianti vineyards lay on tour, tasting, and (sometimes) food packages at affordable prices. It is essential, however, to book these ahead of arrival. Around a week in peak season should be fine—and remember not every cellar runs every type of tour every day.

Castello di Verrazzano is a traditional Chianti wine-maker and the birthplace in 1485 of explorer Giovanni da Verrazzano. All tours include tales of Giovanni's adventures, of course, as well as the manor's Renaissance gardens, historic cellars, and a tasting of reds including the estate Chianti, extra-virgin olive oil, and balsamic vinegar. The basic tour costs €10, and there are several options if you want to upgrade it to add lunch, dinner, or various gastronomic tastings.

If you just want to taste and buy at the estate's counter, there is a sales point beside the SS222, just north of Greve.

Nearby Castello Vicchiomaggio is another historic Chianti estate that runs tours and tastings. The €12 classic tour takes in an informative whisk around the cellars, followed by a three-wine tasting on the panoramic terrace of the estate-owned Cantinetta San Jacopo.

The roadside Bottega di Coltibuono is also open for informal tastings of the Badia a Coltibuono estate wines. The concentrated Chianti Classico riserva is an excellent partner for a hearty Tuscan stew.

For a top-end tasting, stop in at the Osteria di Passignano. A three-glass tasting of Antinori wines ranges from €20 to €35; the range includes reds from the Chianti, Bolgheri (by the coast), and their flagship Tignanello Super-Tuscan.

As well as the vineyard cantinas, it is also worth visiting a first-rate enoteca (wine shop) to get a sense of the variety across Chianti's many producers. Small, niche labels are well represented at the Acccademia del Buon Gusto, in Panzano. Owner Stefano Salvadori always has a handful of bottles on his tasting table, and is one of Tuscany's most knowledgeable and welcoming wine sellers. Sample a few and you'll really begin to appreciate the difference in tastes across various Chianti blends.

In Greve, the walls of the Enoteca del Chianto Classico Gallo Nero are lined, floor to ceiling, with bottle-stacked shelves. Reds are especially well represented, of course; you can pick up something in just about any price bracket, from a few euros to hundreds.

  • Don't miss

    Consorzio Vino Chianti Classico, www.chianticlassico.com

    Castello di Verrazzano, Via Citille 32A, Greti, tel. 055/854243, www.verrazzano.com; cheaper tours only run Monday to Friday (Saturday tours include lunch, and no tours run on Sundays)

    Castello Vicchiomaggio, Via Vicchiomaggio 4, Greve in Chianti, tel. 055/854079, www.vicchiomaggio.it; no basic tours on Mondays

    Bottega di Coltibuono, junction of SS408 and SS429, north of Gaiole in Chianti, tel. 0577/749479, www.coltibuono.com; closed Mondays in November and December, and altogether in January and February

    Accademia del Buon Gusto, Via Ricasoli 11, Panzano in Chianti, tel. 055/8560159, www.accademiadelbuongusto.com

    Osteria di Passignano, Via Passignano 33, Badia a Passignano, tel. 055/8071278, www.osteriadipassignano.com; closed Sundays

    Enoteca del Chianti Classico Gallo Nero, Piazzetta Santa Croce 8, Greve in Chianti, tel. 055/853297, www.chianticlassico.it

Local towns and villages

Greve in Chianti has long been thought of as the Chianti's 'capital'. A market town on a rare flat patch of land, it is also home to the region's major festival: the Rassegna del Chianti Classico marks the grape harvest each September with tastings, gastronomy, and other wine-related festivities.

Greve's regular market runs each Saturday.

The town's major claim to fame is invested in one of its native sons. Explorer and navigator Giovanni da Verrazzano was the first European to sail into what is now New York. A statue in Greve's triangular main square, Piazza Matteotti, marks his achievement.

Just uphill from Greve, Montefioralle is a tiny, fortified village with a famous adventurer of its own. Amerigo Vespucci—the Medici agent and navigator who travelled to the Americas and left the 'new' continent his name—was supposedly born there in 1454.

Capital of the 'Sienese Chianti', Castellina in Chianti is another fortified town, and an original member of the Lega del Chianti (Chianti League) defensive alliance. The Via delle Volte still reeks of the Middle Ages: this intact underground street was used for defence and as a lookout. The town's 15th-century Rocca (fortress) is still standing, and now houses the Sienese Chianti's archaeological museum.

At Radda in Chianti, another founder member of the Chianti League, the focus of the town is its Palazzo del Podestà. Its façade is decorated with over fifty coats of arms of local noble families, dating back to the 1400s.

The Chianti is also well placed for day-trips to some of Tuscany's highlights: Florence, Siena, Colle di Val d'Elsa, and the Valdarno. San Gimignano is around forty-five minutes by car from Castellina.

The outdoors

Much of what is best about the Chianti you will discover on a seemingly endless carousel of panoramas. So many of its roads are scenic—at times drivers have to fight to keep their eyes on the road ahead. The main wine road, the 'Chiantigiana' or SS222, has views right along its length, from Florence's southern suburbs all the way to Siena.

Pause just south of Panzano to take in the Conca d'Oro (Golden Shell), where rows of vines cover what looks like a giant 'scoop' dug from the hillside.

Other scenic roads—pack your camera and use the regular lay-bys and informal parking stops—include the SS429, especially between Poggibonsi and Castellina and between Radda and Badia a Coltibuono. The unpaved strada bianca (literally 'white road') between Greve and the main Siena–Florence road, past the lonely abbey at Badia a Passignano, is unforgettable.

The Chianti is also a good base for cyclists; road and hybrid bike hire is available, by the single day or week, in Greve at Ramuzzi and in Castellina at Chianti 500.

  • Don't miss

    Ramuzzi, Via Italo Stecchi 23, Greve in Chianti, tel. 055/853037, www.ramuzzi.com

    Noleggio Chianti 500, Via IV Novembre 35, Castellina in Chianti, tel. 0577/1481001, www.noleggiochianti500.it

Shopping

As well as wine, Chianti is known for the quality of its olive oil—over 400,000 silver-green olive trees grow across the region. Olives squeezed each November produce a pale but pungent oil that is prized for its extremely low acidity. Like the region's wine, its oil is marked with a DOP quality assurance.

At vineyard Fontodi, by the road just south of Panzano, the organic juice of the frantoio (olive press) is as prized as the estate wine. Use it as close to bottling as possible to get a concentrated taste of the Chianti.

The region is famous for its butchers, too, who sell both raw cuts such as the bistecca fiorentina ('Florentine', bone-in steak) and cured meats. Look out for salami made from Cinta Senese, the local breed of pig prized for its sweet meat. Wild boar salami (salami di cinghiale) is another speciality.

Dario Cecchini is probably the most famous Chianti butcher—for his counter-side recitals of Dante and his 'good meat motto'. The four things an animal must have? A good life, a good death, a good butcher, and a good cook. He provides number three, and careful sourcing ensures one and two are taken care of. Number four is up to you.

As well as meat, he sells a range of condiments that make good gifts, including Profumo del Chianti, a blend of dried herbs and salts for seasoning meat.

In Greve, Falorni sells the best local meat from a shop on the main square. In summer, there are also tables ranged out front, where you can tuck into panini or a plate of cold cuts. Porciatti has been the best butcher and deli in Radda since the 1960s.

It doesn't look like it from the outside, but a roadside workshop between Radda and Gaiole is home to one of Tuscany's most celebrated ceramics producers. At Rampini everything sold by the family business is modeled, fired, glazed, and hand-painted on the premises. Designs are typically Tuscan, with bold colours and motifs from the Tuscan countryside. They can arrange shipping if you can't safely get it home. The quality is first rate.

Just beyond the Chianti's north-eastern fringe, there is designer shopping at The Mall , where you'll find top-end labels like Gucci and Prada at big discounts.

  • Don't miss

    Consorzio Olio DOP Chianti Classico, www.oliodopchianticlassico.com

    Fontodi, Via San Leolino 89, Panzano in Chianti, tel. 055/852005, www.fontodi.com

    Dario Cecchini, Via XX Luglio 11, Panzano in Chianti, tel. 055/852020, www.dariocecchini.com

    Falorni, Piazza Matteotti 71, tel. 055/853029, www.falorni.it; fresh meat counter is closed on Sundays

    Porciatti, Piazza IV Novembre 1, Radda in Chianti, tel. 0577/738055, www.casaporciatti.it; closed Sunday afternoons, and also Wednesday afternoons in winter

    Rampini Ceramics, Casa Beretone di Vistarenni, near Radda in Chianti, tel. 0577/738043, www.rampiniceramics.com; closed weekends between November and March

Museums

With so much emphasis on landscape and flavours, the Chianti is a little under-supplied with great museums. At Castellina, the Museo Archeologico del Chianti Senese focuses on finds relating to the ancient wine-making heritage of the area, which dates at least to the Etruscan era. Visitors can also scale the Medieval tower, for views over the Chianti hills, as far as the Val d'Elsa, Val di Pesa, and Siena on a clear day.

Just outside the town, signposted from the SS222, is the Etruscan burial site of Monte Calvario. Its mound sheltered by pine trees, and tended by the museum, has four tombs that date back to the 7th century BC. Visitors are free to roam in and around the site.

For real museum lovers, Florence and Siena are both easy day-trips from anywhere in the Chianti.

  • Don't miss

    Museo Archeologico del Chianti Senese, Piazza del Comune, Castellina in Chianti, tel. 0577/742090, www.museoarcheologicochianti.it; closed weekdays between November and March

Chianti Chianti Chianti Chianti Chianti

Key contacts

All of the Chianti's major towns have tourist offices. Most are open daily in summer, but service can be patchy in the off-season—it is worth emailing ahead with any need-to-know questions.

At Greve, the office is at Piazza Matteotti 10, tel. 055/8546299, e. info@turismo.greveinchianti.eu. In Castellina, the tourist office is at Via Ferruccio 40, tel. 0577/741392, e. ufficioturistico@comune.castellina.si.it. There are also tourist information offices at Radda (Piazza del Castello 1, tel. 0577/738494, e. proradda@chiantinet.it) and at Gaiole (Via Ricasoli 50, tel. 0577/749411, e. ufficioturistico@comune.gaiole.si.it).

Airports

Pisa (PSA - Galileo Galilei) is Tuscany´s international airport, located about 40 minutes´drive west of Florence. Florence (FRL - Peretola), north-west of the city, is a smaller airport receiving domestic and European flights.

If your villa is in southern or eastern Tuscany, one of Rome´s two airports may be a more practical option: Fiumicino (FCO) is the larger, for international flights; Ciampino (CIA) has a fewer facilities and caters to the discounters and smaller European airlines. Both are just off Rome´s ring road, the GRA, and convenient to all the motorways.

The little airport at Perugia (PEG - Sant´Egidio), in Umbria, is convenient fr eastern Tuscany and receives domestic italian flights and discout airlines from UK.

Insider tip

Allow more time than you think you'll need for journeys around the Chianti. Roads are twisty-turny—every hairpin seems to reveal another panorama—so it is usually slow going on pretty much any route except the 'Chiantigiana', the SS222. You should pack travel sickness remedies for any delicate back-seat passengers, as a precaution.

Best & Finds

  • For the palate. Le Cantine di Greve Greve-in-chianti
  • More for the palate. Castello di Monsanto, Barberino Val dElsa
  • For the appetite. Villa i Barronci, San casciano in Val di Pesa, or il Borgo Antico, Dimezzano/Lucolena
  • For the occasion. Chianti Wine Festival, Montespertoli in May
  • A different point of view. Ballooning in Tuscany