How to See the Best of Tuscany—Beyond Florence—in One Week
Pisa is one of the easiest Tuscan cities to explore both because it’s flat and because nearly all the major attractions center on Piazza del Duomo (also known as the Campo dei Miracoli— “Field of Miracles”). Your half hour at the Leaning Tower, or Torre Pendente, is a memorable, though expensive, experience. You certainly shouldn’t miss the Duomo (cathedral) or Battistero (baptistery), and the Camposanto (burial ground) provides a more contemplative contrast. The Museo dell’Opera del Duomo (cathedral museum) and Museo Nazionale di San Matteo are must-sees for anyone with a keen interest in painting and sculpture.
For dining and nightlife, head into the heart of “real” Pisa, closer to the river, where the city’s produce market still thrives and trattorias abound.
Like Pisa, San Gimignano makes for a doable day trip because its major attractions are tightly packed. Once you've parked, you can easily get around the town, with its ancient streets and medieval towers, in a day. The centro storico centers round the magnificent twin squares of Piazza del Duomo and Piazza della Cisterna. Undoubtedly, the art highlight is the frescoed interior of the Collegiata, no longer a proper cathedral because it doesn’t have a bishop’s seat. Sant’Agostino and the Museo Civico, as well as the ascent of the Torre Grossa, are all within a few minutes' walk.
Seeing Siena in a day is the biggest challenge of your trip. Begin at the functional and spiritual heart of town, scallop-shaped Piazza del Campo. The Lorenzetti and Martini frescoes at the Museo Civico (inside the Palazzo Pubblico) should be your first stop. Serious Sienese art fans should then detour to the Pinacoteca Nazionale, Siena’s picture gallery, for a more in-depth crash-course in Sienese art. After lunch, head for the cathedral complex centered round Piazza del Duomo. You can easily spend three hours seeing the Duomo, the Museo dell’Opera Metropolitana (home of Duccio’s Maestà), and the Battistero. The former hospital of Santa Maria della Scala, opposite the Duomo, is a great spot to end your day. (If you have little ones in tow, it’s here you’ll also find Bambimus, the children’s art museum.) If time remains, squeeze in some shopping and cafe time. Siena is renowned for both craftsmanship and bakery products.
Travel Tip: This itinerary does not leave you much time to relax at your stops. If you prefer to move more slowly, consider sacrificing one of the stops to spend an extra day in Siena.
At one time, Lucca was the unofficial capital of Tuscany, and a Roman colony known to Caesar and Pompey. Today, it’s celebrated for the most complete Renaissance ramparts in Europe. We recommend you start by circumnavigating them on a bicycle. After your ride, you can see the highlights of Lucca from closer up. Although it is light on truly first class museums, the town shelters some of Tuscany’s loveliest churches. Try to visit the Cattedrale di San Martino, San Frediano, and San Michele in Foro, if only to check out their Pisan-Romanesque facades. Leave yourselves time for one of Lucca’s great pleasures: wandering the main pedestrian shopping street, Via Fillungo.
You can see all of Pienza’s major attractions in about three hours, before heading out for your next stopover. The highlights of this model Renaissance town are all in Piazza Pio II (pictured above), chiefly the Duomo, Museo Diocesano, and Palazzo Piccolomini. Wine collectors shouldn’t depart without at least looking in at the Enoteca di Ghino. Grab a porchetta sandwich from Nannetti e Bernardini and make for your next stop, Montepulciano. Plan to arrive right after lunch, so you can see Montepulciano’s attractions before nightfall. The unmissable sights here are the Cattedrale, the Tempio di San Biagio (just outside the gates), and the Palazzo Nobili-Tarugi. Leave time for tasting some Vino Nobile: Gattavecchi is my favorite cellar in town. End your day with one of the best steaks you’re ever going to eat, at Acquacheta.
For your final look at Tuscany, Arezzo won’t disappoint; it’s the major reason to visit the northeastern part of the region. Its steep medieval streets were made for walking (in sensible shoes), but the chief attraction is painted inside the Basilica di San Francesco: Piero della Francesca’s Legend of the True Cross. Book your timed entrance slot as soon as you hit town. If you’re rushed, you can skip the Duomo, but don’t miss the Pieve di Santa Maria, crazy-sloping Piazza Grande, or a trip to the Casa di Vasari, native-son Giorgio’s old digs. The city goes very quiet during the afternoon riposo (Italian siesta), so I try to make lunch at Gastronomia Il Cervo stretch through the middle part of the day. If you’re not due back in Florence until the following day, Arezzo has a couple of stylish, central boutique accommodations at very fair prices.