Radda in Chianti is a typically Tuscan medieval town in the cooler mountains of the Chianti Classico region. The beauty of the setting matches seamlessly with the elegance of the wines produced here, which come from thousand year old crops, and it’s the wine-related name that draws many people to this picturesque spot. Our recommendations for the best places to stay in Radda in Chianti are also perfectly matched to the surroundings, and to the wines produced. They’re all traditional in style, some converted from hilltop farms, or wine estates, and many offer incredible views of the valley, and the Tuscan hills beyond.

There’s something about this region that suggested wine production to the Etruscans, who planted the first cultivated vines here around 2300 years ago, and even during the regular pattern of fighting and fortification that this region has experienced in those past couple of thousand years, wine has always been produced. This is worth mentioning, because these hills are littered with the remains of forts and ancient lookouts, some which have become part of the grounds of vineyards, or of the country estates on our list.

The best places to stay in Radda in Chianti are an obvious pick for foodies. The vineyards, with their cellar doors, winery tours, tastings, and opportunities to pick or watch traditional wine production methods, are a huge draw for anyone with an interest in food and wine. And the setting is magical. But it doesn’t stop with what’s in your glass, this region also produces olives, white beans, fennel, chard and kale; and is known for its wind boar salamis, guinea fowl, and for its pecorino. There are little restaurants, cafes and bars dotted all over Radda in Chianti, on little piazzas, in the narrow medieval walkways or ‘tunnels’, on the edges of town where there are terrace overlooking the valleys, and of course in the vineyards.