Tuscany trip planner

A vacation guide to help you plan the perfect trip to Italy's Tuscany region

Tuscany

Top destinations in Tuscany
• Florence
• Siena
• Pisa
• San Gimignano
• Lucca
• Chianti
• Montepulciano
• Pienza

Tuscany is one of the richest and most rewarding regions in Italy. It is home to the art of Florence, the Leaning Tower of Pisa, and the wines of the Chianti.

Tuscany is the birthplace of both the Renaissance and the modern Italian language. Tuscany is a region where the restaurants serve marathon dinners and the churches in even a small city are stuffed with the kind of Renaissance art that would take pride of place in any major world museum.

The vine-striped valleys and ancient hill towns of Tuscany comprise a Italian fairytale landscape right out of a painting—perhaps one by local boy Leonardo da Vinci. Even the short list of Tuscan luminaries reads like a who's-who of cultural giants: Da Vinci, Michelangelo, Galileo, Botticelli, Dante, Giotto, Petrarch, Boccaccio, Puccini...

If you have to pick one region outside the major cities to explore, make it Tuscany.

Top destinations in Tuscany

The Duomo of FlorenceFlorence - Birthplace of the Renaissance, hometown to Michelangelo, Leonardo da Vinci, Botticelli, Donatello, Giotto, and dozens other of Old Masters—and repository of Michelangelo's David, Botticelli's Birth of Venus, Ghiberti's Gates of Paradise, Brunelleschi's dome, and 1,001 other seminal works of art and architecture. To break up the Art History 101 nature of it you can peruse the artisan workshops of the Oltrarno, bargain in the San Lorenzo leather market, dig into a hearty meal of bistecca fiorentina steak with Chianti wine, and find a hotel for your own, perfect Room with a View moment... More

The Leaning Tower of PisaPisa - Pisa's "Field of Miracles" is a grassy lawn sprinkled with some of the most gorgeous Romanesque architecture in Italy, from the Duomo (in which local luminary Galileo discovered his law of pendulum motion by watching the swinging chandeliers) to the statue-studded Baptistery (home of an intricately carved pulpit and near-perfect acoustics) to the famous church bell tower that just can't seem to stand up straight, giving pizza restaurants the world over something to print on their delivery boxes... More

Top experiences in Tuscany
• Surveying Renaissance art at the Uffizi in Florence.
• Touring the castles and vineyards of the Chianti.
• Climbing the Leaning Tower of Pisa above the Field of Miracles.
• Indulging in a 3-hour Tuscan dinner at Il Latini in Florence.
• Biking around Lucca atop its 16th century walls.
• Tasting wines in the Etruscan cellars of hilltown Montepulciano.
• Getting your Gothic art fix in Siena then strolling its shopping streets.
• Ascending the medieval stone skyscrapers of San Gimignano.
• Sampling Italy's best goat cheeses in Pienza, the perfect Renaissance village.
• Clambering up inside Brunelleschi's famous cathedral dome for a 369-view of Florence.

The Campo in SienaSiena - This Gothic antidote to Renaissance Florence is an overgrown hilltown of fine food, brick palaces, and a laid-back lifestyle. It's civic buildings and the mighty zebra-striped Duomo are filled with some of the greatest examples of late Gothic painting in Europe, and its streets are crowded with strolling locals, not blattering automobiles... More

San GimignanoSan Gimignano - The "Medieval Manhattan" is unique in Italy for being the only town to preserve more than a dozen of its medieval stone towers, holdovers from the bad old days of the Middle Ages bristling the skyline above vineyards producing one of Italy's finest white wines... More

Piazza Anfiteatro Romano in LuccaLucca - Elegant city girdled by mighty 16th century brick bastions (the tops of which have now become a tree-shaded park encircling the city) where everyone gets around by bicycle. Fantastic Romanesque churches, Renaissance frescoes, fine opera, a piazza that takes its form from an ancient Roman amphitheater, and one-tenth the crowds of nearby Pisa... More

Cantina de Redi in MontepulcianoMontepulciano - A postcard Tuscan hilltown of Renaissance palazzi lining the steeply sloping main drag and warrens of Etruscan-era tunnels burrowed through the rock underneath the palaces that now house some of the finest wine cellars in the world—and, more importantly, where the wine tastings are free... More

PienzaPienza - In the middle of the Crete Senesi—the picture postcard Tuscan landscape south of Siena of rolling grasslands, grazing sheep, and marching lines of cypress—rises the tiny town of Pienza, famed for its sublime pecorino (sheep's milk cheese) and delightful Renaissance architecture. Pienza is miniscule—just nine blocks long and still encircled by medieval walls—but has a major draw in the form of its central piazza. Thanks to the quirky ambition and deep pockets of a homegrown pope, the main square of Pienza was completely overhauled by architect Bernardo Rossellino as an homage to all those paintings of "the perfect Renaissance city"... Full story

The ChiantiThe Chianti - The hills of the Chianti stretching between Florence and Siena comprise one of the world's most famous wine-producing regions. The steep slopes are cloaked in terraced rows of vines and peppered with medieval castles and cypress-shrouded abbeys. The narrow valleys are laced with tiny rivers along which are sprinkled small market towns. The Chianti is the perfect place for a countryside getaway—and a great base for exploring Tuscany for the comfort of a rental villa or country hotel. At the very least, take the slow road—the SS 222, a.k.a. the Chiantigiana—on a day-long tour of the Chianti's wineries, winding your way leisurely though these misty, wine-sodden hills between Florence and Siena... Full story

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This material was last updated February 2011. All information was accurate at the time.

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