Regarding specific winery suggestions, we have an endless list all depending on the type of wine drinker you are. Are they enthusiastic about wine but not obsessed? Are you just looking more for a great tasting experience? Are you wine collectors that really want to make important purchased for shipping home and are specifically looking for high end wines?

Regarding wine tastings you can choose between Montalcino and Montepulciano (both in the Val d’Orcia region that are 45-50 minutes driving from the Castello) or the Chianti area (as close as 20 minutes, extending all the way to Florence). There are two approaches to the tasting experience: an open tasting with no appointments necessary or an intimate experience by appointment. 

Here’s a quick list of wineries where you can show up without appointment and do tastings:

Poggio Antico in Montalcino -big, commercial producer with a restaurant inside if you want to stay for lunch https://www.poggioantico.com/en/
Fattoria dei Barbi  in Montalcino– similar to Poggio Antico, also has restaurant inside https://www.fattoriadeibarbi.it/en/
Tenuta Fanti in Montalcino – easy drop in location but suggested to make an appointment. Additionally has option for eating but must be done with more than one day advance notice (website for information https://www.tenutafanti.it/en/visit)
Felsina in Chianti– the closest of Chianti wineries. This can easily be visited on the way to or from Siena as it is conveniently located nearby the highway.  https://www.felsina.it/en/
Villa Sesta in Chianti– easy stop on the way into the heart of Chianti https://www.villasesta.com/en/

Castello Brolio in Chianti- visit the incredible structure and gardens on location for €5 and receive a free wine tasting at the cantina below https://www.ricasoli.com/en/cellars/ 

Otherwise, if you prefer to arrange a schedule, here are our top picks for wineries that offer tastings by appointment: 

NostraVita in Montalcino – This is by far the most unique experience. It equates to going to your best friend’s house that happens also to make Brunello. Don’t expect stellar wine critic ratings as this is too small and not focused on glitzy image for that. This is their home and there is nothing like it anywhere. www.nostravita.it 

Podere Le Ripi in Montalcino – Owned by the Illy coffee family and is home to the Banzai Brunello vines. Cult following, very sophisticated but young and energetic. Some of the best views in all of Tuscany.  https://www.podereleripi.com

Tolaini in the heart of Chianti Classico region, this winery makes Chianti, but the real focus has been Super Tuscan blend wines that are born to compete with all the big names in France and California. Very personal and informative tour and tasting. Starting as of 2019, it is also possible to do a full day at the winery, including lunch and painting lesson. www.tolaini.it/en/

De Ricci in Montepulciano – most beautiful ancient wine cellars, perhaps in all of Tuscany, very convenient and superb hospitality. https://www.cantinadericci.it/en/

Poliziano in Montepulciano – in my opinion the best producer of Vino Nobile with a very impressive facility https://carlettipoliziano.com/en/