Chianti: a food and wine itinerary

Judy Witts takes us on a tour to discover Chianti's flavours

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Judy Witts

Judy Witts
HomeAway travel expert

Chianti Food and Wine Itinerary by Judy WittsThe Chianti wine road, the 222, is the original road from Florence to Siena; and, back in medieval times, the cities were rivals and governed separately. It’s said that during their feud to settle the borders, the cities set off riders when their respective cocks crowed, and where the riders would meet would become the new border. Legend has it, however, that because the Florentines starved their rooster and he woke up early from hunger, the border between Florence and Siena is now closer to Siena.

The 70 kilometre drive takes you through some of Tuscany’s most beautiful scenery, home to Chianti, Chianti Classico and some super Tuscan wines. Wineries abound, but to tour, reservations are a must. Taking time to get lost is what makes this area so incredible, and it's a wonderful homebase for a stay.

Hill towns, hamlets and castles abound, and every village has something special to offer.

 Besides the vineyards, of course, you will pass olive groves and woods, home to wild boar and deer, so don’t be afraid to go off the paved roads: they're perhaps less travelled, but they will always ensure great views. Allow time for a long lunch, and remember: most shops close for an afternoon siesta.


Sample Chianti's gorgeous gastronomy


Greve Greve

Considered to be the region's capital, Greve has one of the loveliest piazzas in Chianti. Under the loggias surrounding its piazza are many wonderful shops and bars where you can simply stop and enjoy people watching. There is also a wonderful wine tasting experience to be had in the old cantinas, located near the large grocery store on the main road. The Falorni butcher shop is also unmissable (it's the perfect place to stop and get supplies for a picnic), as is the tiny hamlet of Montefioralle, located up the hill. One of the most photographed in Chianti, it has remained untouched for decades.

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Lamole Lamole

Lamole is worth the detour. The main road leading from Greve to Panzano has a turn-off to this tiny village, home to just a few dwellings with a small piazza and church. But it's the microclimate people travel for, which guarantees fabulous wines. They have their wine festival the last weekend in May usually, but it's worth the visit year-round. As you drive up the hill, you may want to stop at the Villa Vignamaggio, once home to the Mona Lisa; the painting's not there now, of course, but the winery is! Their tour is simply lovely, as it allows you to soak up the Renaissance gardens as well.

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Panzano Panzano

Most people visiting Chianti in the past simply drove by Panzano, heading to other towns; until the butcher at the Macelleria Cecchini, Dario Cecchini, made himself famous. Stop here for a quick burger or a longer and luxurious tasting menu: both are worth the visit! They also serve lunch on Sunday and dinner during the week, and even with a fixed menu, it's a great experience. If you are staying in a rental property, Dario has many items to go, so you can also enjoy eating at home. Bear in mind that the village also attracts many artists, so don’t miss the art studios in town, which include works by painters, sculptors and ceramicists. Beyond the piazza is the original upper town, complete with castle. Drive through town and out the back to get a great view of the castle from the nearby hill.

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Castellina Castellina

The centre of Castellina is blocked off to traffic, which makes it a fun town to walk around. It was once a fortress, and today, you can still walk down around the town through the tunnel which was used to protect the village. Now it boasts a restaurant, winery and a few other shops, but like most towns, there are plenty of other tiny alleys which should be explored. Going up by the city hall, there is a great trattoria, La Torre, and in the main part of town, the tunnel will lead you to some of the best gelato in Chianti. The large store is just outside the town on the main road, which also leads to some interesting Etruscan tombs.

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Radda Radda

Radda is another lovely village with a view. Parking can be had around the outside of the walled-in town, which is simply brimming with shops selling local specialties, and wineries; some of which have tasting rooms. There is also an incredible design shop located at the end of the town near the outside wall, where they make and sell ceramics, small affrescos, iron work and clothing all designed and made by a lovely husband and wife. The view from the outside wall, looking towards La Volpaia, has got to be one of my favourites in Chianti.

View holiday apartments in Radda in Chianti


Photo Montefioralle © lo.tangelini

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