1

To be honest not somewhere that lights up for a 2 year old. Montepulciano has great wine tasting possibilities, check out Pienza for its incredible Peccorino, Siena is close, I suppose for an infant Lake Trasimeno would be quite nice.

2

Montepulciano it's a very nice town. For sure some good wine testings of the local "Vino Nobile": we were to a winery called "Contucci" up in the main square and we could visit its old cantina in a few thousand years old cave. There was a funny old guy there whose name is Abramo (he's the man) who gave us so many wine shots of the different wines they produce (at the end we were almost drunk)...we really liked it!
Our driver took us to a local trattoria called "Diva & Maceo" at the entrance of the old town and their food was terrific!! You will have fun in this nice medieval town!!

3

Thanks very much - very helpful indeed! :-)