Visiting Radda in Chianti – where to stay, eat and taste outstanding wine

If you think of visiting Tuscany for wine tourism, we (as Italian wine specialists) certainly recommend that you spend a couple of days in the medieval village of Radda in Chianti. Lost in the mountains of Chianti Classico, this area is cooler and drier than the rest of the province, and it’s home to Tuscany’s most elegant wines. Here’s our recommendations which are the best restaurants of the area, where to stay and where to enjoy wine tasting. We hope you find this guide useful.

Set on a hilltop amongst a sea of vines, the medieval town of Radda in Chianti is typically Tuscan. Small cobblestone lanes meander up past quaint buildings, which sit stacked atop each other. Around each corner you’ll find panoramic views allowing you to take in the surrounding scenery.

Grapes have been grown in the region for more than a thousand years, so it’s unsurprising that Radda is home to some of Chianti’s most elegant wines. It’s easy enough to reach by aeroplane, located just nine miles north of Siena and 22 miles southeast of Florence.

We spoke to Annalisa Chiavazza from the Castello di Radda winery about the best places to stay, eat and taste wine during a trip to Radda.

Cobbled street in the village of Radda in Chianti, Tuscany, Italy

Where to stay in Radda in Chianti

Borgo Vescine Loc. Vescine, 53017 Radda in Chianti, Italy | Tel: +39 0577 741144

Il Borgo di Vescine is a truly magical place to visit. Restored by Lucia Paladin, the property began as a Langobardic fortress. The small village is an exceptional place to stay with 28 unique rooms and suites showcasing its history and authenticity. The small central terrace, or piazzetta, is the place to be for sunset drinks. The views from the grounds are exceptional, as Borgo Vescine sits on a hilltop overlooking Radda in Chianti, with olive trees and vineyards perched on terraces hemmed in by dry stone walls. The on-site trattoria specialises in Tuscan fare, with a particular focus on grilled meat and local extra virgin olive oil.

Agriturismo Borgo Castelvecchi Loc. Castelvecchi, 53017 Radda in Chianti, Italy | Tel: +39 0577 738050

The Borgo Castelvecchi farmhouse is just ten minutes drive from Radda in Chianti, and is the perfect spot for a tranquil escape. The rustic manor is surrounded by stone buildings, which are host to the spacious rooms and apartments. Each one has been tastefully decorated in classic style, with visible wood beams on the ceiling and terracotta flooring. On-site amenities include an outdoor swimming pool with breathtaking views over the Chianti hills, and a restaurant offering typical local cuisine. The agroturismo is also home to historical wine cellars, which date back one thousand years.

Palazzo Leopoldo  Via Roma 33, 53017 Radda in Chianti, Italy | Tel:: +39 0577 735605

This elegant Palazzo Leopoldo hotel is set inside a medieval manor house hotel sits in the heart of Radda in Chianti, just a short meander from the Rectory of St Nicolas. The rooms focus on old world style, with rustic décor (as well as flat-screen televisions and free Wi-Fi). Some rooms have balconies with views over the village and the hills of Chianti, while some upgraded suits have fireplaces and dining areas. The hotel has an on-site restaurant serving up Tuscan cuisine and a spa which offers wine-themed treatments.

Hotel Palazzo San Niccolò Via Roma, 16, 53017 Radda in Chianti, Italy | Tel: +39 0577 735666

The Palazzo San Niccolò sits proudly in the main square of Radda in Chianti. The rooms are decorated in typical Tuscan style with frescoed ceilings and terracotta floors. There’s a sunny courtyard on the ground floor where guests can enjoy breakfast in the morning and wine in the evening. There is also a spa, featuring a jacuzzi on an outdoor terrace. The hotel provides cookery classes so you can try your hand at learning how to make hearty local fare.

Best restaurants to visit

La Bottega di Giovannino Via Roma, 6, 53017 Radda in Chianti, Italy | Tel: +39 0577 738599

Opened in 1965, this wine bar and shop specialises in sharing platters of Tuscan cured meats, cheese and bruschetta to accompany a wide selection of Chianti Classico. They also have a small and simple selection of pasta and salad.

Osteria Le Panzanelle, Lucarelli Località Lucarelli 29, Panzano in Chianti | Tel: +39 057 773 3511

Enjoy generous portions of regional cuisine including homemade pasta and roast meat at this rural trattoria. The fare is simple and has been awarded Bib Gourmand status by the Michelin Guide.

Il Girarrosto Via Roma 35, 53017 Radda in Chianti, Italy | Tel: +39 0577 735605

This restaurant belongs to the Palazzo Leopoldo hotel, however it is a fantastic place to eat even if you aren’t staying overnight. It specialises in typical Tuscan cuisine, crafted from high-quality ingredients.

Borgo Castelvecchi Loc. Castelvecchi, 53017 Radda in Chianti, Italy | Tel: +39 0577 738050

Part of the Agriturismo Borgo Castelvecchi, the excellent restaurant is currently open by reservation and serves delicious local food.

Bar Ucci 9 Piazza della Torre, 53017 Radda in Chianti SI, Italy | Tel: +39 0577 738042

This wine bar is set inside an old cattle-shed, and is run by ex-winery worker Paola Barucci. Her excellent wine list includes fantastic bottles from all over Tuscany, with a special focus on Chianti Classico. This is accompanied by rustic food and cakes.

Where to go wine tasting

Castello di Radda winery main building, Radda in Chianti, Chianti Classico, Toscana, Italy

The Azienda Agricola Castello di Radda ( sits on the hill east of the village of Radda in Chianti, underneath the castle of Volpaia. The vineyards face southeast to southwest, perfect for soaking up the sun, and are grown on pebbly clay and limestone soil. This is especially well suited to Sangiovese and Canaiolo grapes, which are used to make some of the wineries exceptional reds.

Wine tastings and tours are available on request. Either book by telephone on +39 0577738992 or via email on

How to experience Radda food and wine at home

While we wait for international travel to be possible again, you can recreate the feel of a Tuscan wine holiday at home in the UK. Start with a bottle of wine from Castello di Radda – we have a number of award-winning wines from them, including:

Exceptional Vigna Il Corno Chianti Classico Gran Selezione which boasts complex flavours like balsamic, coconut and eucalyptus.
Light and fruity Sangiovese rosé with elegant flavours of raspberries, jasmine and grapefruit.

Limited edition Guss Super Tuscan with deep flavours of dark cherry, chocolate, cinnamon and smoke.

Next, cook a Tuscan-inspired feast to accompany it. Chianti Classico wine goes particularly well with meat, making the perfect partner for red, white and game. Try whipping up rabbit alla cacciatore – a hearty stew rich in tomatoes, garlic and red pepper. Guinea fowl roasted with herbs, like rosemary, makes for an elevated take on the classic Sunday chicken. Tuscan beef stew – fortified with a splash of red wine – is a heartwarming option perfect for cool evenings dining al-fresco in the garden.

To learn more, read our Guide to finding the best Italian red wine for steak, pork, venison or lamb

Icon of grilled steak - Italian wines for steak, pork, venison and lamb