I have found great rentals to stay in each of these towns, so I'm down to the final decision. We plan to stay a week in early May (husband and two teen boys). We will have a rental car which I assume we'll park outside the walls of either town. We are from a small town ourselves (4,000) so don't need a ton of attractions, just a historical hill town with some interesting sights, restaurants, shops, that we can enjoy when we're not daytripping elsewhere. Is Montepulciano so focused on wine that there's not much else to check out (regarding shops, etc.)? Any difference between access to the town if we're parking outside the walls and our apartment rental is within? (We don't really want a 1/2 hour hike every time we need our car.) Other differences or suggestions?