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Fly into: Pisa Fly out of: Pisa
Total Duration: 9 days

Cypress trees, vineyards, and rolling hills characterize this gorgeous region of central Italy. Wine and olive oil have been produced here for centuries, and they help make meals something special. On this road trip, you'll see lots of important art in Pisa and Florence, then wind your way through the scenic countryside of Chianti, ending up in Siena.

    This Trip's Top Experiences:

  • Natural Beauty
  • Food and Wine
  • Art and Culture
  • Architecture
Days 1-2
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1 Pisa & Lucca

Towers and Ramparts

  • Pisa's Leaning Tower has been marveled at for centuries, but it's only one of the city's allures
  • Lucca's exquisite Duomo has an ornate façade strewn with colonettes and contains a haunting, beautifully sculpted tomb by Jacopo della Quercia
  • Make like the locals and stroll atop the ramparts that encircle Lucca's city center
  • Art and Culture
  • Architecture
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Days 3-4
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Minerva_Bloom/Fodors.com member

2 Florence

Heart of the Renaissance

  • Make reservations in advance to visit the Uffizi, the world's greatest collection of Renaissance art
  • Visit the Duomo, admire Brunelleschi's groundbreaking cupola, and climb to the top if you have the stamina
  • Visit the Accademia and marvel at Michelangelo's David, his Slaves, and his St. Matthew
  • Experience convent life while contemplating the tranquil paintings by Fra Angelico housed in Museo di San Marco
  • Art and Culture
  • Museums
  • Shopping
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Days 5-6
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3 Greve in Chianti

Chianti Country

  • Sample the region's wine at any of the terrific enoteche lining Greve's oddly shaped Piazza Matteotti
  • Drive the Strada Chiantigiana, the beautiful roadway winding through the heart of the region
  • Stop in at Castello di Brolio, a centuries-old castle and vineyard
  • Food and Wine
  • Natural Beauty
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Day 7
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4 Montepulciano

Wine and Art

  • Stroll the cobblestone streets of this classic hill town, ascending to the magnificent Piazza Grande (the main square)
  • Sample area's signature wine, the lusciously rich Vino Nobile di Montepulciano
  • For a dose of culture, visit the church of San Biagio, a fulfillment of Rennaisance architectural ideals
  • Food and Wine
  • Art and Culture
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Days 8-9
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5 Siena

Crypts and Museums

  • Bask in the sun in Piazza del Campo, arguably Italy's most beautiful square
  • Inside the Palazzo Pubblico, check out incredible frescoes by Simone Martini and Ambrogio Lorenzetti
  • Visit the monumental Duomo, with its fantastic marble floor, vibrant frescoes in the Biblioteca Piccolomini, and more great frescoes in the crypt
  • Art and Culture
  • Architecture
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