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.

The Best Places to Stay in Radda in Chianti

For the Views

• La Locanda is a small, hilltop hotel, with wonderful traditional Tuscan charm, and incredible vineyard and valley views. Inside this converted villa are seven beautiful rooms and suites, which feature original details like terracotta floors, beamed ceilings and exposed stone floors, plus a collection of elegant but homely antiques. Each room is different, but our favourites have private terraces. There’s also a delightful library, a bar and lounge. Outside is a shaded terrace and a divine infinity-pool-with-a-view.

For a Rural Escape

• Relais Vignale is an 18th century country house, carefully and sympathetically restored to its traditional elegance, and transformed into a 42 room country hotel. Rooms have terracotta-tiled floors, whitewashed walls, and exposed beams on the ceilings, plus a collection of simple, locally made antiques. Outside there are gardens, a lovely outdoor pool, and a Tuscan terrace restaurant with vineyard and olive grove views. 
• Il Borgo di Vescine is a collection of 13th century stone buildings in a hamlet, now turned charming hotel. There’s plenty of privacy, space and peace, but also the opportunity to enjoy the company of fellow guests in the restaurant or on the terrace, where local cuisine is served, paired with local wines. You’re just 20 minutes from Siena, but there’s plenty to do onsite, including wine tastings, cooking classes, horse riding, using the gym and pool, or exploring the grounds. Explore further afield on the hotel’s bikes.

For Great Value

• The Palazzo Leopoldo is a traditional Tuscan hilltop hotel with just 14 rooms and suites, and a beautiful restaurant with incredible valley views and a welcoming terrace. The decor is perfectly Tuscan, with terracotta-tiled floors, exposed beams on high ceilings, and a collection of antiques. There are hot tubs on the terrace, and an indoor pool in the cellars, along with a luxurious spa.

Prefer a Private Apartment or Villa?

• If you'd prefer the privacy of a self-catering option then browse through the wide variety available online with our partner, Booking.com.

Travel Information

• The closest international airport to Radda in Chianti is Florence Airport, Amerigo Vespucci, which is about an hour away by car, taxi or transfer, or about two hours away by rail. Pisa Airport is Tuscany’s largest, so it’s also worth considering, at about an hour and a half away by car or taxi, or about two and a half hours away by rail.
• If you want to hire a car we recommend you visit our online partner, Rentalcars.
• Chianti is busiest — and hottest — during July and August. If you’re interested in doing some wine tastings plan for July rather than August, because it’s cooler in the hills of Chianti, and you’ll be able to test the white and rose wines while watching the workers cutting the leaves back on the red vines. Some of the cellar doors close during August — the workers there go on holidays too! September and October are the harvest months, and this is when the vine leaves are at their most colourful. It’s a great time for foodies, or anyone planning to do any walking. Spring, or April and May are lovely for walkers too, and Easter is a huge colourful celebration in Tuscany. Winter is cooler and darker, but there’s plenty to recommend Chianti around Christmas as well.

Still not sure where to stay?

• You could expand your search to include all the best places to stay in Tuscany
• Refine by the type of hotel you’re looking for: the best wine hotels in Chianti for example, the best hotels in rural Tuscany or the best family hotels in Tuscany
• Or you could contact one of our friendly Gurus for personalised advice.