Tuscany Wine Tour Through the Back Door

Hi all, Any idea how to tour Tuscan wineries through the back door? A group of four of us are going to Tuscany in May and we'd like to see lots of wineries around Orvieto, Montalcino, and Montepulciano. We plan to enjoy the wine and we recognize that the wineries are scattered about and largely not within walking distance of the towns so traveling by car will be necessary. However, we do not want to tour a local jail so we'd like someone else to drive us. We've spent some time looking and it's obvious you can spend lots of money for a sanitized tour that would probably be about as informative as a pub crawl. We're looking for a wine experience that is great for us and isn't offensive to the proprietors. We also recognize that the best experiences often happen at the whim of a local rather than pre-planning based on visiting websites and doing Google searches. Thanks for any tips, insight, or connections!

Posted by Kelley
Buffalo, NY, USA
7 posts

Where (what town) will you be staying at the time you wish to do the winery tours? I will be there in June and will be staying in Siena. I have never booked a tour (I usually like to do my own thing and avoid being a member of a herd of tourist cattle) but have this time for the same reason you mentioned (jail avoidance). I went with Tours by Roberto. The company is highly recommended on this site as well as others, I am a research freak and have not come across any negative comments about them. I received an extremely prompt response (within minutes - no joke). Tours are never more than 8 people in a mini van, take from Siena or Florence, and apparently if you are the first to reserve with them for a particular date, you have a lot to say about what the itinerary of the day will be. www.toursbyroberto.com good luck!

Posted by Simon
19 posts

The idea of driving yourself round the wineries is appealing, however as you have realized it may not be such a good one in practice. There a several companies that provide this exact service: we went with Slow Days wine tours from Florence and had a great day. I think they may also do tours from Siena but you'll have to email beforehand to be sure. Enjoy!

Posted by Zoe
Toledo, Ohio, US
6053 posts

I've never taken a tour but when I stayed in Siena I met several people who were touring with Roberto and they were thrilled with it. I met Roberto briefly as he was collecting his tour group and he was warm, enthusiastic and gave lots of information and encouragement.

Posted by Justin
Albuquerque, NM, United States
8 posts

Thanks Kelley, Simon, and Zoe! I'll contact Roberto and Slow Days. I appreciate your recommendations. Justin