• Ciao Laurync — your timing is perfect, as I’m getting many requests right now for recommendations on wineries to visit on a self-guided tour in Chianti.
    A couple of questions before I give you some recommendations:

    How many days are you planning to do wine tasting in Chianti?  Do you have specific days in mind for your wine tasting? As a general rule, weekdays and sometimes Saturdays are best.  Sundays are tough and many wineries are closed.
    How many wineries would you like to visit in a day?  I usually recommend no more than 3 with a nice lunch or dinner in the mix.  Italian winery visits can easily last 60-90 minutes, as the producers love to show you around the cantina and the grounds.
    Do you prefer smaller, more family-run wineries, or larger, big name wineries?  As a general rule, the smaller wineries tend to be more informal, friendly, and no tasting fees and you usually meet the winemaker & family.  Big-name wineries have more formal tasting rooms, fancier facilities, sometimes have tasting fees, and you tend to visit with knowledgable staff.
    Do you want to drive, or would you prefer to have someone drive you?  I see that you have a car, but there are car services available that can pick you up, drive you around, and drop you off at the end of the day — a wonderful way to enjoy the wines and lunch without worrying about driving.

    Post your answers here and I’ll follow-up with some recommendations.

    • Hi Michael, thanks for your quick response. Here are my answers to your questions. Let me know if I don’t fully address anything:
      1. We will be in Chianti for 5 days. We would like to spend at least one day wine tasting in chianti… Unless you think we are doing ourselves a disservice by not doing more. We also plan to get down to Sienna and the surrounding areas to do wine tasting on another day. We do not have any agenda – so can be flexible to go during the week.

      2. I am with you, 3 is usually a good number for one day.

      3. I would prefer small family run wineries. We are originally from Northern California, so this isn’t our first rodeo. Haha. We have seen plenty of big wineries and are excited to feel a little more italian charm. Our biggest problem, however, is that none of us speak Italian. I don’t know if that is a problem with the smaller places. But again, we are flexible if you feel there are some bigger ones not to be missed.

      4. We are open to hiring a driver if the price is right. Please let me know if you have any recommendations.

      One last thing- depending on the wineries you suggest, I wonder if you have a recommendation for a great place to eat along the way? Maybe we could do one winery before lunch and two after…or something.

      Thanks again!