Tuscany is just really lovely. No one has ever said anything bad about it ever. I overuse words like "enchanting" when I'm here quite a bit.
Last time I was in Tuscany, I was a youngish backpacker seeing Europe on the rails, which meant mostly big cities with occasional forays into the countryside. While I highly recommend taking public transportation pretty much anywhere, sometimes it's just easier to rent a car and really see the countryside.
We stayed at a lovely agritourismo called La Lucciolala, just outside the ancient hilltop village of San Gimignano. It was so quiet and at the end of a rather rutted dirt drive, but a good jumping-off point to explore some small towns and villages in the region.
Not only do they have lovely views tucked into the hills, they make their own wines.
Chianti wines aren't necessarily my favorite, but, while in the Chianti region, it's time to drink Chianti. Most of them weren't half-bad, with some having an overpowering astringency that I dislike.
But, eh, part of the charms of traveling with family is keeping a steady buzz to be able to deal with each other with manners and grace, and that was the plan we all stuck to.
My favorite thing about this trip was the farmhouse-style dinners. The hillsides are practically slathered with rustic little farmhouses willing to feed you. You don't get a choice of the menu, but you get served with a big group, family-style. The food was always fantastic, and I found the local white wine, while not so popular, was pretty drinkable. My favorite discovery was a blood-red tomato and bread soup. Totally rustic peasant food, but I couldn't stop eating it.