In Tuscany, the horizons are studded with centuries-old villas and stately cypress trees; roads wind through vineyards and olive orchards. In this slice of earthly bliss, the sun seems to shine brighter, the people seem friendlier, and the food—ah, the golden polenta topped with wild boar ragu—it all tastes better in Tuscany. This 9,000-square-mile region in central Italy, with Florence at its heart, is the birthplace of Leonardo da Vinci, Michelangelo and Botticelli; of Renaissance architecture and Chianti wines. Every village is crammed with ancient stone buildings and shops selling prosciutto, pecorino and fresh ravioli. A week-long visit—especially in spring and fall, when temperatures are mild and roads unclogged—is the perfect way to indulge in Tuscany's glorious scenery and ambrosial food and wines.
Day 1: Lucca 45 miles west of Florence.
Start with a morning stroll along Via Fillungo, Lucca’s busiest street. Church bells ring (Lucca is known as the city of 100 churches) and bicycles whiz past shop windows displaying everything from Benetton to biscotti. A gray-haired woman in church clothes unlocks the tall Torre delle Ore, a 14th-century tower where a 208-step climb leads to an awe-inspiring view. Another good way to see Lucca is from the high city walls, which have been turned into a 3-mile, tree-lined promenade. Puccini pilgrims flock to the apartment where the great composer once lived, preserved much as he left it (Corte San Lorenzo 9). Before you leave, stock up on provisions and Lucca’s famed olive oil at a store called Lucca in Tavola (Via San Paolino 130/132); for wine, visit Enoteca Vanni (Piazza del Salvatore 7; enotecavanni.com).
Day 2: Pisa 65 miles west of Florence.
Most travelers visit this ancient town for the famous Leaning Tower, which you can view from the grassy Campo dei Miracoli or climb ($22 entrance fee; book in advance at opapisa.it). Just a few feet away are Pisa’s cathedral and baptistery, whose ornate Romanesque design reflects a time when the town’s maritime power rivaled that of Genoa and Venice. Stroll south to the Piazza dei Cavalieri, the grand main square in the center of the medieval quarter, where former palaces are now university buildings. Residents and students gravitate to the square’s outdoor cafés, to sit and chat over pizza and big bowls of ribollita, a hearty soup of beans, kale and chunks of bread rubbed with garlic.
Day 3: San Gimignano 40 miles southwest of Florence.
This walled town high on a hill is often called the Medieval Manhattan, because its 14 stone towers, built by warring families during the Middle Ages, resemble miniature skyscrapers. Enter via the main gate, the Porta San Giovanni, and stroll along a cobblestone street towards the beautiful Piazza della Cisterna, the town’s main square. Inside the 13th-century Palazzo del Popolo—located on the adjoining square, the Piazza del Duomo—check out the Museo Civico’s fresco-bedecked rooms and an intimate gallery of Gothic and Renaissance paintings (Piazza del Duomo; $6). Climb to the top of the attached Torre Grossa (large tower) for superb views of the town and countryside. Then stop at Gelateria di Piazza (Piazza della Cisterna 4) for the Crema di Santa Fina—a saffron ice cream that’s surprisingly delicious.
Day 4: Siena 45 miles south of Florence.
The deep red hue of Siena’s buildings was Crayola’s® inspiration for the name of its reddish-brown crayon. Narrow lanes leading into the main square are lined with shops selling handcrafted shoes, freshly pressed olive oil, striking ceramics (some of the best are at Ceramiche Artistiche Santa Caterina, Via di Citta 51, 74 and 76) and more. This beautiful town is famous for the Palio, a colorful, chaotic horse race held twice a year on July 2 and August 16, as well as its black-and-white-striped cathedral, one of the most notable Gothic churches in Italy. Step inside to see the marble-inlaid floor, the Donatello sculpture of St. John the Baptist and a 13th-century pulpit carved by Nicola Pisano. Leave time to visit the richly frescoed rooms at the Palazzo Pubblico (Piazza del Campo; $9), and the Pinacoteca Nazionale (Via San Pietro 29; $6), which documents the city’s historical and artistic heritage with art from the 14th to 17th centuries.
Day 5: Montalcino 75 miles southeast of Florence.
Tiny Montalcino may lack the excitement of Siena’s Palio, but it has its own claim to fame—this is where they make the luscious Brunello di Montalcino, justifiably one of Italy’s best-known wines. Along the steep, winding streets are more than a dozen enoteche, or wine shops, where you can pick up a bottle of Brunello for anywhere from $20 to $1,000. Sample a few glasses at busy Caffé Fiaschetteria (Piazza del Popolo 6). With all the quaffing going on, the town’s handful of Romanesque churches are usually tourist free. The diminutive Museo Civico e Diocesano d’Arte Sacra is a good place to see Renaissance paintings (Via Ricasoli 31; $6). For the best views, climb the 14th-century Fortezza (Piazzale Fortezza; $4), and then retire to the in-house enoteca for another glass of vino.
Day 6: Pitigliano 120 miles southeast of Florence.
The first sight of Pitigliano is startling: The town sits high on a tall crag of volcanic rock called tufo, and the houses, made from the same stone, look as if they have sprouted from the mountain. Here you’ll find superb Tuscan restaurants and shops, as in the larger towns—but at a much more tranquil pace and with far fewer tourists. A thriving Jewish community existed here until World War II (Pitigliano is still known as “Little Jerusalem”); the 16th-century synagogue (Vicolo Manin 30; $4) still remains. The town’s other main attraction is the Palazzo Orsini (Piazza Garibaldi; $4), a medieval palace displaying works by the 18th-century painter Francesco Zuccarelli. Stroll through elaborately decorated rooms that once belonged to the powerful Orsini family—medieval decadence at its best.
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