This route brings you to Italy's must-see destinations: Florence, Siena, Pisa, Lucca, and the Chianti.
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.
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.