Perfectly Pair Food And Wine At Tuscany's Best Vineyard Restaurants

Monday, September 14, 2026
Posted in: Chianti Food and Wine Localities Restaurants & Cafés Wineries & Breweries
Dining

Whenever we recommend basing yourself in one of the wine areas of Tuscany, we have certain images of these sorts of vacations that immediately come to mind: cycling between nearby vineyards in the Chianti area, wine-tasting in a historic cellar or a beautiful room overlooking the famous rolling green hills of Tuscany, picnicking among the vines, or dining in a more formal and excellent restaurant with the vineyards as a backdrop. If you are interested in the latter, in particular, then you might be interested in the list of the best vineyard-restaurants around the world that was recently put together by renowned viniculture publication Wine Enthusiast magazine


Of the 57 spots listed all around the globe, four are located in Tuscany alone. So, if you want to plan a perfect pairing of food and wine during a stay in one of our villas in Tuscany, then read on and discover these wineries that serve both in beautiful spaces...

Osteria di Brolio, Chianti


With a cosy dining room surrounded by leafy greenery, elegant plating, and gorgeous wines, this osteria in the heart of the Chianti region is open for both lunch and dinner. Of their dining philosophy they say: “Osteria di Brolio is the place where flavors, scents, stunning landscapes, and inebriating wines of Tuscany come together. In the plate, in the glass, in the soul. Our greatest aspiration has always been to let our land's ingredients tell their stories: oils with character, tasty meats, fish from the nearby sea, vegetables from our gardens, cheeses from local master cheesemakers. With this spirit - respectful of the territory and its extraordinary history - Osteria interprets the seasons: its roots anchored in tradition and a bold look to the future.” Book a vacation rental in Chianti and come sample the incredible dishes and delicious wines on offer while taking in the surrounding scenery...


Madonna a Brolio, 53013, Gaiole in Chianti

+39 0577 730290


Il Ristoro di Castello di Ama, Chianti


This restaurant offers intimate dining spaces located on the main floor inside the 18th-century Villa Pianigiani. Emphasising conviviality, they pair the “drinkable” Great Wines of winemaker Marco Pallanti with incredible seasonal set menus of the day. For foodies looking for an exclusive wine tasting and tour experience paired with a meal or just a meal and glasses or bottles as you wish, this stunning location is an ideal setting for an unforgettable experience.


Località Ama in Chianti, 53013, Gaiole in Chianti

+39 0577 746031


Ristorante Campo del Drago, Montalcino 


Boasting truly stunning and sweeping views over vineyards, hills, and mountains, this gem has gained two Michelin stars for its contemporary Tuscan cuisine. Chef Matteo Temperini gives a highly personal and creative spin to regional dishes and makes use of produce grown in their own garden. With both three different tasting menu and the option of choosing à la carte and a wine list of over 700 labels (including by-the-glass selections), you can devise your own perfect dining experience in the elegant and contemporary dining room of this slick and well-oiled winery while staying in one of our villas in Montalcino.


Località Castiglion del Bosco, Montalcino, 53024

+39 0577 191 3135


Indigeno, Montepulciano


Last, but not least, there is this slightly more relaxed but no less impressive option. Listed in the Michelin Guide, it is set within the Salcheto Organic Winery and its charming 13th century farmhouse among the rolling green hills around Montepulciano. Serving simple and traditional Tuscan fare that savours heritage and rich flavours, they make use of ingredients produced right on the farm on the estate or from local small-scale suppliers. With shared tables are located indoors or outdoor tables set within the grounds, this is a welcoming place to enjoy classics done really really well while staying in a holiday rental in Montepulciano.


Via Villa Bianca, 15, 53045 Montepulciano

+39 0578 799031


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