Get a wide-wheeled stroller. Cobblestone streets are tough on the small wheels of most travel strollers. If your small child gets tired easily, you'll need a stroller that can handle rough road. The stroller can also come in handy if there's a transit strike (which happens frequently). Transport your luggage in the stroller and you won't be dependent on buses, cabs and vaporettos (Venice's water buses).
Sign up for a family tour. Backroads (see Resources) runs specially designed family tours in Italy, with biking, hiking and an itinerary suited to children. Small groups ensure individual attention, and the guides can entertain children to give adults some alone time.
Live like the Italians and rent an apartment or house. Explore the area for a few days, then move on to another region and another rental. You can save money over hotel rooms, have more room, cook a couple of meals and even do laundry. Rentals are plentiful in Tuscany, Rome and Venice.
Pack your kids' favorite snacks. In Italy, you are never far from a gelato shop or an espresso bar where a kid can have steamed milk. But a box of a favorite cereal from home, bags of nuts and dried fruit, and a jar of peanut butter can keep kids fueled between meals.
