Tuscany vacation planner

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

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

Florence - 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, Brunelleshci'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...

Pisa - 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 belltower that just can't seem to stand up straight, giving pizza restaurants the world over something to print on their delivery boxes...

Top experiences in Tuscany
• Surveying Renaissnce 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.
• Acending 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.

Siena - 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...

San Gimgnano - 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...

Lucca - 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...

Montepulciano - 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...

Pienza - In the middle of the Crete Senese—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 (sheeps' 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"...

The 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...

Tips

Planning your time: Tuscany is one of the richest and most rewarding regions in Italy. If you have to pick one region outside the major cities to explore, make it Tuscany. If you give Florence at least 2-3 days, give the hilltowns of Tuscany at least another day or two—preferably three days. I have prepared some perfect itineraries to help you plan a trip to Tuscany lasting anywhere from a single day to an entire week.
Rent a car: Although there are excellent rail connections to some towns (Florence, Pisa, Lucca), workable—if not ideal—train connections to some others (Siena, Montepulciano), and buses can get you to the others (San Gimgnano, Pienza), having a rental car will really pay off. This is especially true since the best bits of Tuscany lie down dirt roads and side roads: the smaller hilltowns, the vineyards, the hilltop castles. I wouldn't attempt the Chianti in anything but a car.

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