Here my personal suggestions for great wine tastings in Chianti:
Badia a Coltibuono: a ancient Abbey producing great wines. The location is beautiful and here you can even enjoy typical Tuscan food at their restaurant. Badia a Passignano:ancient monastery all surrounded by a scenic landscape. The cellars are very ancient and here is also a fantastic osteria.
Castle of Brolio: beautiful and famous castle in Chianti, great for wine tastings. You can also visit the castle and its museum.
In Val d’Orcia, located south of Siena, and famous for great wines like the Brunello of Montalcino and the Nobile of Montepucliano, I recommend:
Ciacci Piccolomini: Located in Montalcino near the wonderful Abbey of Sant’Antimo, this winery offers pretigious wine labels and has 3 beautiful wine cellars.
Biondi Santi: very famous name for the Brunello of Montalcino
Fattoria Poggio Grande: in this typically Tuscan farm you can taste great wines in a familiar atmosphere. While passing acrooss Tuscany and its enchanting countryside you’ll see a lot of signs for wineries and wine tastings, feel free to stop where you most like and just taste!
Contact me again for any other advice,
Have a great day, Elena
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