We are finalizing plans for our trip to Italy this coming June (2017), and I have some questions. I've gotten great advice in the past from this forum, so wanted to ask here again. Our last trip to Italy, in 2015, we enjoyed 2 days in the Montepulciano area, roughly 15 minutes outside of Montepulciano itself, at an agriturismo. We will be driving. We enjoyed the Tuscan countryside so much we'd like to extend our time for this trip, slow down a little, take a cooking class or a wine tasting class, and really enjoy things. I envision some days perhaps driving off to another town in Tuscany, sightseeing, shopping, having a great lunch, coming back mid afternoon, maybe going for a swim (we have a 10 year old son, the swim is a big part of the day for him), then going out for an evening dinner somewhere close by, ideally walking to it.
But this time I'd really like stay right in the town/city we stay out, so we can do that walk to dinner. My initial thought was to plan for Montepulciano again, but I am realizing that there aren't many hotels/B&Bs close enough to walk (an even less with pools). There are fabulous restaurants in Montepulciano, but maybe even more in Siena. Siena has even more places to stay. I've heard Siena is magical in the evening. Siena also might be a little more central to places we want to go - we can easily get back down to Montalcino, but also Volterra and San Gimignano are nearer.
So my question is - what would folks recommend? Stay in Montepulciano or in Siena? Any specific hotels or agriturismo's folks would recommend? Again ideally we're at walking distance into whichever place we choose.
BTW - rest of the trip, we will be doing a day or two staying in Florence, so we will keep our time in tuscany for smaller more rural places. :)
Thanks!
S