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The Tuscany region of Italy spans 8,900 square miles, from the vibrant urban centers of Florence, Siena and Pisa to quaint villages nestled in the countryside. This itinerary starts in Pisa, though you can also begin your journey from Florence.
Pisa (2 hours)
When in Rome … or Pisa … take funny perspective photos with the 700-year-old leaning tower, and admire the other Romanesque buildings carved from marble that occupy the Square of Miracles. The Cathedral of St. Ranieri is named after Pisa’s patron saint and has a fantastic ceiling of recessed square panels decorated with gilded embellishments. The Baptistery of St. John is the largest in Italy, recognizable by its ornately carved Gothic dome.
Florence (2 days, 1-2 nights)
Ninety kilometers east of Pisa is Florence, a romantic Tuscan city brimming with history. The Cattedrale di Santa Maria del Fiore’s striking façade of pink, white and green marble creates the magnificent focal point of the Piazza del Duomo. Trek up more than 400 steps to the cathedral dome, and look over the city’s red-tiled rooftops.
See Michelangelo’s 17-foot-tall marble achievement, David, and countless other priceless masterpieces at the Accademia Gallery. Watch the sunset and peek in showroom windows gleaming with gold jewelry along the much-photographed Ponte Vecchio, home to goldsmiths since the late 1500s. Compare prices of beautifully stitched leather accessories at various boutiques before choosing the right souvenir. Sample the local cuisine with tasting (assaggio) platters of pastas, steaks, cheeses and desserts at Acqua Al 2.
Greve in Chianti (2-3 nights)
Perhaps the best way to experience Tuscany is to sojourn at a restored villa or farmhouse tucked amid vineyards, rolling hills and forests. Cycle on winding roads, attend a cooking class, or lounge on your villa’s patio with a glass of Chianti Classico.
Castellina (3 hours)
From centrally located Greve in Chianti, you can easily day trip around the region. Castellina was razed and reconstructed repeatedly during the feud between Florence and Siena in the Middle Ages. Shop along the Via delle Volte, a tunnel once used by soldiers that is now a promenade of unique boutiques.
Monteriggioni (3 hours)
Discover old Italia in Monteriggioni, which is still enclosed by 30-foot-high stone fortifications that connect a network of 14 guard turrets. Plan your outing to coincide with the annual medieval festival. Each July, the town is transported to the time of knights, lords and ladies — you can even exchange euros for medieval currency to make purchases from local merchants.
Siena (1 day, 1 night)
Feel the excitement build as you ride up a series of escalators from new to old Siena, where tiny streets, family-owned shops, elegant ristorantes and dozens of gelaterias await you. Though smaller than the Florence Duomo, the Cathedral of Siena is astounding inside and out. Within the cathedral, the Piccolomini Library has 500-year-old frescoes that have retained their vibrant shades of blue, gold and red.
All roads lead to Piazza del Campo, Siena’s famous public square that looks today much as it did centuries ago. Each summer, the competitiveness and camaraderie of Siena’s neighborhoods culminate in the Palio, as the piazza becomes a horse race circuit and grandstand.
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