Two weeks will give you enough time to see Tuscany's top destinations with some additional time to sample the treasures of Umbria and the pleasures of the Val d'Orcia.
Days 1-2: Florence
The sights most easily tackled together are the Cathedral, the Baptistery, Giotto's bell tower, Orsanmichele, and Santa Maria Novella. Except on Sundays, these are open until early evening, making them suitable opening-day attractions. Then, unwind with some comfort food at the casual Il Santo Bevitore, a glass of wine in the Oltrarno, and top it off with a frozen treat at the Gelateria dei Neri.
After waking up early with a frothy cappuccino, the second day is best suited for more stimulating sights. Not to be missed are the monastery-museum of San Marco and nearby, the Accademia, to view David; the refined landscapes of the Boboli Garden; and at least a brief tour of the Uffizi.
Be sure to check the opening hours of all museums before planning your itinerary and make reservations for the Uffizi and Accademia. Some museums are closed on Monday, and a few churches are closed during the lunch break. Because the rest of the itinerary requires a car, you should book one well ahead of time since reservations fill up quickly (especially in summer).
Day 3: Prato & Pistoia; Lucca & the Garfagnana
Art and architecture buffs would be remiss to skip Pistoia and Prato. Continue on to Lucca and plan to overnight here. Stroll along its walls and savor a romantic dinner of tortelli lucchesi in its alleyways. The next day, you have a choice of getting some more exercise in the Garfagnana, one of Tuscany's most pleasant natural preserves, or more sightseeing in some of the region's lesser-known cities. The road to the caves and hiking trails of the Garfagnana is short and very scenic, but the excursion realistically will take most of the day -- especially if you break your journey with a meal of typical local food at the Antica Locanda di Sesto.
Day 4: Pisa
Consider getting up for a morning bicycle ride along Lucca's medieval walls before making the short drive to Pisa. Climb the Leaning Tower, snap the de rigueur photo, visit the rest of the Campo dei Miracoli, then drink and dine in the "real" center of town.
Day 5: Volterra & San Gimignano
Visit the Alabaster City of Volterra, a medieval remnant and former center of the Etruscan world. After lunch, head for San Gimignano. The best time to approach San Gimignano is in the late afternoon, when the hilltop city is bathed in the setting sun. Get to the Collegiata before it closes.
Day 6: Siena
Unless you're there during the Palio, the top sights in Siena can feasibly be visited in about 1 full day. The cathedral is one of Italy's most interesting, especially if its elaborate intarsia pavement is uncovered. The Museo Civico inside the town hall houses the most important secular frescoes in Tuscany. Be sure to indulge in a feast in Siena, as its food is one of its greatest draws.
Day 7: Chianti
Spend the day on state road SS222, which takes you through the big-name towns in Chianti, and all the way back to Florence. The three most worthy stops are Greve, Panzano, and Castellina in Chianti, all sitting at the heart of important winemaking areas. Although there are a number of great restaurants along the way, those on a tight budget might want instead to pick up picnic supplies in Panzano, and pay a visit to the "poet butcher," Dario Cecchini, who can recite Dante's Inferno in its entirety while chopping away at a rack of ribs. Be aware that many vineyards are family-run and require prebooking to tour.
Day 8: Cortona & Arezzo
Aside from the marvels of Piero della Francesca in Arezzo and the gorgeous, hilly streets of Cortona, the adopted home of Under the Tuscan Sun author Frances Mayes, one of the nicest parts of this day will be the ride between the two. The SS71 is studded with castles, vineyards, and sunflower fields. In fact, finding a nice bed-and-breakfast outside one of the towns will make for one of the trip's most memorable nights.
Day 9: Perugia
The city's National Gallery is a must-see on any visit to Umbria, but just hanging around the cafes of this animated medieval city makes it worth the trip. Central Italy can be rather short on nightlife for young people, but Perugia's university scene makes the city a welcome exception. Don't forget to sample those Perugina Baci chocs.
Day 10: Assisi
This is the most revered shrine in all of Italy, with the Basilica di San Francesco second in importance only to St. Peter's. It will take the entire day to explore all the city's art, from Giotto's paintings to the recently restored Rocca Maggiore fortress. Make time for the tranquil Eremo delle Carceri and lunch at La Stalla.
Day 11: Montefalco, Todi & Spoleto
Wine lovers should spend most of the day in and around the capital of Sagrantino, Montefalco, visiting family-owned vineyards. Otherwise Todi, one of the quaintest towns in all of Central Italy, is worth a quick visit. End the day in Spoleto, home of the country's most famous outdoor festival of the performing arts. Check your calendar to see if you will be there during that time.
Day 12: Orvieto
Make a detour on the road to Orvieto to reach Chiusi, a bonanza of Etruscan urns, tombs, and other impressive remains. Approaching Orvieto in the evening offers you a gorgeous view of the city illuminated by sunset, or spotlights at night, and is an ideal stop for dinner and some of its "liquid gold."
Day 13: Montepulciano & Montalcino
Make your way into the Val d'Orcia via Montepulciano and from there to Montalcino. These two wine-producing giants are worthy stops in their own right, especially the former for its handsome, palazzo-lined Corso. Between the two is the model Renaissance city, Pienza, surrounded by the kind of captivating Tuscan landscape you see in promotional photos.
Day 14: Depart Florence
Reserve this day for last-minute leather shopping in the Scuola del Cuoio and choosing Renaissance scents from Santa Maria Novella, then to catch whatever sights you missed on the first 2 days.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.