My wife and I (60/fairly active) are attending a wedding in Monticchiello in June. (Traveling from US) Other than that weekend, I have ten days open (before the wedding). I'd love some suggestions, keeping in mind that our three days/nights in Monticchiello will be mostly occupied by wedding activities and no sightseeing/hiking/etc. Because we have visited Rome, Venice, Florence, Cinque Terre, Dolomites (all of which I'm hoping to be lucky enough to visit again), we plan to explore within a few hours of the wedding destination: perhaps fly into Bologna and stay for the first few days and then make our way to Montichiello, visiting Siena, San Gimignano, Volterra (and possibly bypassing Florence, entirely, though that just seems silly: but maybe it's sillier to visit Florence for just a few hours while driving by).
We like food, but lean toward local rather than fancy. We like hiking and walking, but also like boats and trams and funiculars. We like trains but enjoy driving. We aren't big shoppers but we like local crafts and art. We don't usually sit by a pool for days, but a little down time is nice.
Also, when we visited Florence we did not get to venture out of the city. I've not seen this area, at all, and I do understand people will come and spend weeks! (months!)
We plan to rent a car in Bologna (as we depart Bologna?) and drive, because I assume that the wanderings between Bologna and Monticchiello are easier/better if we have our own car.
We are leaning toward an Agritourismo for accommodations, but maybe we will do a hotel here and there. Perhaps by the time we get to Monticchiello we will want a hotel (in Montepulciano?)
Would love to hear folks random ideas, but my wife and I are starting our independent research, as well. A travel video online about Bologna was intriguing.
Perhaps my most important question is, how many places would you stay between Bologna and Monticchiello? Would you simply stay near Siena at one establishment, or would you stay in two different locations?