Help with add on days to trip to Tuscany

I recommend the Dolomites - we loved it in August a few years ago. The mountains are beautiful and pleasantly cool, the villages so quaint. We just drove around, following whatever road grabbed our fancy. Around mid afternoon, we began looking for guesthouses that had an available room sign advertised. We checked out the room before we agreed to stay and we just stopped overnight (you can handle almost anything for one night but most were basic and clean). We saw lots of different places and weren't tied to one spot. It might be a nice change since you plan to remain in one place in Chianti. What I recall best on that part of the trip was not the usual tourist "sites" per se (churches, overlooks etc) but the inexpensive 3 course lunch we didn't realize we ordered and were so full by the 2nd course we were too stuffed for dinner, the charming villages nestled into the valley, the scenery changes driving through the mountains, the lunch nook dedicated to bears...

Another idea, since you are coming into Milan, is to go to the Lake Como region, which we also visited. It's just beautiful there however, it is more expensive than just finding a village guesthouse in the dolomite area.

Personally, Milan leaves me cold, although I enjoyed looking at the high fashion areas. But I was more than happy to leave it, to see the Lakes region and the Dolomites. Of course, Venice is supposed to be amazing but from what I hear, I would leave that for another trip when you can go in the shoulder season. The atmosphere seems too crazy during the summer to be able to enjoy the city to it's fullest, IMHO.

If you're looking for something cooler, then the cities are not the place to go. If you want to spend several days/nights enjoying city life, then consider time in the cities. Yes, Venice will be busy in July, but I've found it easy enough to escape the tourist crowds by heading away from San Marco (though the last time I was in Venice in July was years ago).

We finally visited Milan several years ago, after passing it up on multiple trips, and I actually enjoyed it a lot. It has several very nice smaller museums, and contrary to my expectations, it wasn't filled with Italians dressed to the hilt. But for a 3-day break, if you want to visit a city, consider Florence or Venice. Florence, even though you said you'd do it as a day trip, is fun at night. In Piazza della Republicca, there's invariably an American singer entertaining passers-by (or maybe not American, but singing American songs). It was this way the last time we visited Florence, about 10 years, and the same last year, when we took our 10yo to Florence.

If you're looking for a cooler location, then I would think the Lakes Region would be easier to get to than the Dolomites. The Dolomites, I would think, would offer more active activities for your kids. Use google maps or viamichelin to get an idea of the driving times to each location.

You might want to reconsider a day trip into Florence, even. It seems airless and stifling on hot days, and with the overwhelming crowds you will not enjoy it much. I suspect your kids won't like it! Actually, it's better to be there in the evening. if you can manage that, taking the train to and from Florence, it would be better if you must go.

For kids the age of your kids, I think Lago di Como would be a snooze.

Lago di Garda has the attraction of Gardaland, the big italian amuseument park which by report most American loves, plus hydorofoil rides to towns where lemons are gown under glass, there is mountain biking, windsurfing, lots and lots of ice cream. With a car, you can also make a foray into Verona -- which will be hot and filled with opera goers -- but it has a great Roman arena (where the opera takes place), a Roman theater, and a terrific castle, plus a lot of toruisty Roman and Juliet kitsch. Were it me, I would give very strong consideration to actually going to the opera one night with the kids.

If Lago di Garda doesn't appeal, Lago Maggiore is also full of fun activities -- boat rides to islands with palazzos that have antique puppet theaters and peacocks, and calbe car rides way high into the mountains for hikes. WIth a car, you can slip over to Lago di Orta as well, or go to tiny hidden lakes on the shores of Maggiore, nice little towns, even Switzerland for an afternoon.

And it's easy to get to Malpensa from there.

Thanks for the great suggestions. I had thought seriously about Stresa as a base for the lakes. If anyone has thoughts about that I'd love to hear them.

Stresa gives you lots of kid-friendly options, and if you have a car, you can see more than one lake. If it rains, it's only an hour's train ride to Milan, where you should be able to find some kid-friendly things to do.

I don't know if your kids have developed any special interests (and maybe they change so often at that age, you can't plan too much in advance!) but don't forget that Italy specializes in perfecting all kinds of things. The race track of Monza isnt far from lago Maggiore. Milan has a science museum. There are cheesemakers and candy and cookie makers all over the place. People who make musical instruments (lago d'Orta is a center for the making of wood-instruments). And of course there are sports teams.

Must you fly into Milan? Have you looked for flights into Pisa? Or even Venice? The latter would make a good easy-going start to your trip. And both adults and kids like Venice.