Tuscany is densely populated with tourist attractions, perhaps more so than any other region in Europe. It could take months to experience all of its art, architecture, food, and wine. Admirers of Michelangelo and Piero della Francesca could spend 2 weeks in Florence and Arezzo. Wine buffs could sip and sniff their way through 2 weeks in Chianti and Montalcino. Romantics could dream away that time in Lucca alone. I've designed the 1-week and 2-week itineraries for first-time tourists to discover the best of Tuscany and Umbria. Then there is a tour for families, and one for food-and-wine enthusiasts as well.
A car will be indispensable in every case, because public transport leaves a lot to be desired. And the soul of Central Italy is found in its countryside, through its sunflower fields and sloping vineyards, spotted with storied castles.
It is not a large place -- you could drive from the top of Tuscany to the bottom on the highway in about 3 hours -- but the roads of the hinterland are windy, narrow, and slow. Don't be daunted by the idea of spending much of your time in the car. Getting there, in this case, is half the fun.
The following itineraries all start in Florence -- the lion's share of travelers from North America arrive there via train, from airports in Milan or Rome. You might, however, consider flying into Pisa, a destination for many low-cost airlines, and begin your itinerary there.
As is the case on any vacation, timing is everything. Avoid peak season if at all possible. So many foreigners, especially Americans, descend on Florence in July and early August that they are literally corralled through the streets. Iron railings on the most populated sidewalks keep the herds from spilling into traffic. Spring and early fall are the ideal times to visit. Families should keep an eye on festival schedules to give children a chance to smash walnuts with mallets in Cortona, for example, or to watch "knights" joust in Arezzo. Enotourists will get the most out of a vineyard visit just before harvest, when the grapes are still on the vine.