The Chianti for beginners

Chianti for first-time visitors

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Donald Strachan

Donald Strachan 
HomeAway travel expert

Chianti vineyard landscape in Tuscany The corrugated hills cloaked in pine, chestnut, and oak run for miles and miles. Fortified towns and rose- and terracotta-coloured farmhouses peek above a sea of vines and olive groves. The food is hearty; the red wine is pressed carefully from the native sangiovese grape.

The scenery and lifestyle of Tuscany’s Chianti hills is every bit a match for the clichés and kitchen calendars. But where to begin? And how to see the best of it on your first visit?



Donald Strachan’s verdict on the Chianti for first-time visitors



  • History: For centuries, the cities of Florence (to the north) and Siena (to the south) squabbled over the Chianti hills, and they are dotted with castles and fortified farmhouses as a result. Some of the earliest date to the period of the Lega del Chianti (or Chianti League), a defensive alliance formed between the towns of Castellina, Radda, and Gaiole in the 12th and 13th centuries. Indeed, the region is still divided, by modern provincial boundaries, into the “Florentine Chianti” and “Sienese Chianti”.
  • Wine: They have probably been making wine here in “the land of the black rooster” since the Etruscan period, centuries before the Romans arrived. Chianti wine has some of the oldest rules denoting where it can be grown and what can go into it—the earliest date to 1716. Look out for “Classico” on the label, which denotes the original and highest quality grape zone; “Riserva” means it has been aged for longer in oak barrels (at least two years). The classic drive takes wine lovers along the SS222, the Chiantigiana, or Chianti Wine Road, past rolling vines and countless marquee wineries. Anyone with a deeper interest in winemaking should book a cellar visit at Castello di Monsanto, well away from the main Chianti trails.
  • Food: A random roadside lunch can be a taste revelation: the powerful flavours of the Chianti’s food are the perfect foil to its robust wines. Traditional, rustic pasta sauces are made from game such as wild boar (cinghiale), hare (lepre), or rabbit (coniglio). Meat forms the backbone of most menus—a simple tagliata (sliced steak) is the classic secondo. Tomatoes are another staple, and the main ingredient on a bruschetta, in panzanella (a salad of tomatoes, olive oil, basil, and bread), and pappa al pomodoro (a viscous soup-stew). The region is also famous for its butchers—buy meat to prepare yourself at a villa—and extra virgin olive oil, strong, aromatic, and low in acidity.


Top places to visit in the Chianti


Castellina in Chianti Castellina in Chianti

Strategically sited on top of a knoll, Castellina wears the evidence of its history as a fortress town. Via delle Volte is an underground street that was used as a lookout and defensive position. The town’s former Rocca (castle) now houses a Museo Archeologico that focuses on finds relating to the winemaking traditions of the area (and you can climb its tower, too). Just outside town (signposted off the main road) lies Montecalvario, an intact Etruscan tomb complex that you are free to explore. It dates to the 7th century B.C. Nearby, indulge at L’Antica Delizia, the Chianti's best gelato stop.

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Greve in Chianti Greve in Chianti

The “capital” of the Florentine Chianti sits among some of Tuscany’s prettiest scenery. It is also home to the region’s liveliest wine festival, the annual Rassegna del Chianti Classico, which marks the wine harvest each September with a host of tastings. On Greve’s curious triangular piazza, Piazza Matteotti, you’ll also find Falorni, one the Chianti’s best butchers, and great for salami as well as fresh meat. Osteria Mangiando Mangiando serves up the Chianti’s traditional, carnivorous flavours.

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Radda in Chianti Radda in Chianti

This whole place reeks of the Middle Ages—Radda was one of the original members of the Chianti League and its formidable Palazzo del Podestà is covered in the coats of arms of powerful historic families. The hills around the town are made for wine touring: there’s tasting at the roadside shop of Badia a Coltibuono (their Riserva is especially good). Castello di Volpaia runs tours and tastings around in its cellar in a spectacular spot four miles north of town. During the olive harvest (November and December) you can also taste their freshly-pressed oil. Booking (by email or phone) is essential.

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Panzano Panzano

Food and drink bring you here—but also scenery, because the view across the vines of the Conca d’Oro (Golden Shell) south of town is among the Chianti’s most photogenic. Panzano is best known for its butcher, Dario Cecchini. As well as supplying first-rate meat for cooking back at your villa, Dario also runs a few restaurants. His version of fast food is served Monday through Saturday lunchtimes at Dario DOC: a breaded burger, “chips” with sage and garlic, and sides of pickles and onions for just €10 a head. For an insight into the Chianti’s wine traditions, as well as tasting, head uphill from Dario’s to the Accademia del Buon Gusto, the Chianti’s friendliest wine shop.

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Day trips Day trips

A fast and free, though slightly hairy, four-lane road runs alongside the Chianti. This “SI-FI raccordo” puts the Renaissance city of Florence within easy reach of most of the Chianti. There is also a regular bus service from Greve and Panzano. To the south, Siena is also easy to reach by car (and, unlike Florence, has well-signed car parks). To the west, the medieval town of San Gimignano is another for the shortlist. To see it at its best, arrive early or stay late—it is a magical place when the day-trip crowds have thinned out.

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Piazza in Greve, Chianti © Konrad Lawson
Radda in Chianti © Rick Cooper
Chianti, Tuscany © John Spooner


Villas in Chianti

Villa near Florence and golf club, private pool, A/C, ideal for family holidays

This villa, located 10 minutes drive from Florence, set on the hills, just outside the town, is a perfect holiday house, to visit Florence and surrounding areas. It includes 6 bedrooms, 5 bathrooms, fully equipped kitchen and washing machines, fre...

Villa / Farmhouse / Home in Barberino Val D'elsa with 2 bedrooms sleeps 4

Welcoming complex comprising 14 units situated on the Chianti hills on a large farming estate producing olive oil, wine and spirits. This property, offering beautiful panoramic views, is surrounded by cultivated fields and by 10 hectares of beauti...

Villa / Farmhouse / Home in Barberino Val D'elsa with 2 bedrooms sleeps 5

Welcoming complex comprising 14 units situated on the Chianti hills on a large farming estate producing olive oil, wine and spirits. This property, offering beautiful panoramic views, is surrounded by cultivated fields and by 10 hectares of beauti...

Villa / Farmhouse / Home in Montaione with 2 bedrooms sleeps 4

Nice hamlet comprising 5 farmhouses which have been completely restored and turned into 16 welcoming apartments, situated a short distance away from the town of Montaione, in the heart of Tuscan country-side. The property's central location is con...

Villa / Farmhouse / Home in Impruneta with 1 bedrooms sleeps 4

Located at Impruneta, a small town at the edge of Chianti, Villa Saladini is a typical old Tuscan Villa. Surrounded by the gentle Chianti hills, the 6 hectare estate, owned and managed by the Morici family for over 200 years, is located less than...
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