In Two Weeks

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 countryside.

Days 1-2: Florence

The best-known and most easily viewed sights to tackle early are the Cathedral, the Baptistery, Giotto's bell tower, and Santa Maria Novella. Except on Sundays, these are open until early evening, making them suitable opening-day attractions. Make sure you have made reservations at some of the top visited sights, such as the Accademia, to avoid the long lines. Then, unwind with some comfort food at the casual Il Latini, and top it off with a treat at the Festival del Gelato.

After waking up early with a frothy cappuccino, the second day is best suited for the more stimulating and rewarding sights. Not to be missed are the monastery of San Marco; Michelangelo's remains in Santa Croce; the Boboli Gardens; the Accademia, to view David; and at least a brief tour of the Uffizi.

Be sure to check the opening hours of all museums before planning your itinerary and, when possible, make reservations. Many museums are closed on Monday and most 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), and pick it up at the airport.

Day 3: Fiesole, Prato & Pistoia; Lucca & the Garfagnana

Art and architecture buffs would be remiss to skip Pistoia, Prato, and Fiesole. Continue on to Lucca and plan to overnight here. Stroll along its walls and savor a romantic dinner of tortelli lucchesi in its alleyways, most notably at La Buca di Sant'Antonio. 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.

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, then visit the rest of the Campo dei Miracoli.

Day 5: Volterra & San Gimignano

Visit the Alabaster City of Volterra, an excellent example of Etruscan culture and one of the lesser-known gems in Tuscany. After lunch, head for San Gimignano; make a very brief stop in Monteriggioni to tour the fortress. The best time to approach San Gimignano is in the late afternoon, when the hilltop city is bathed in the setting sun.

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 with its recently discovered new room, the so-called "crypt" underneath, containing a cycle of 13th-century frescoes. 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 222, which takes you through the big-name towns in Chianti, and all the way back to Florence. The three most worthy stops are Greve, Radda, and Castellina in Chianti, all important winemaking areas topped by medieval villages. 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 therefore close on Sundays.

Day 8: Cortona & Arezzo

Aside from the marvels of Piero della Francesca in Arezzo and the bucolic setting around 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 village 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.

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.

Day 11: Todi & Spoleto

Prospective real-estate buyers will be tempted along the vineyard-lined road to Todi, where myriad Americans and Britons have made a second home. The town is one of the most quaint in all of Central Italy, and is worth a quick visit. End the day in Spoleto, home of the country's most famous outdoor festival of the performing arts. By all means, check your calendar to see if you will be there during that time.

Day 12: Orvieto

Two great stops on the road to Orvieto: Chianciano Terme, where you can do like the Roman soldiers and take the "cure" at its thermal springs, and 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 south along the ancient Via Cassia to Montalcino, and then to nearby Montepulciano. These two wine-producing giants are worthy stops in their own right, even for those uninterested in wine. Nearby 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 San Lorenzo market and to catch whatever sights you missed on the first 2 days.