Itineraries for Your Trip to Tuscany
3 Days in Tuscany for First Timers
One of the first things that struck me on my initial visit to Tuscany was its massive size. Tuscany spreads across a vast swath of central Italy, stretching from the balmy Tyrrenhian coastline to the forested peaks of the Apennine mountains.
The secret to a successful Tuscan trip is to divide the region into smaller areas and devote a day to exploring each. With three days, you’ll be able to savor the landscapes of the Val d’Orcia, the hill towns and wineries of Chianti, and the art and architecture in Lucca and Pisa. With scant public transportation, you’ll need a car or private transportation to reach most smaller towns. Here’s how to make the most of three days in Tuscany.
Tuscany has four distinct seasons, with hot summers, cold winters, and unpredictable spring and fall temperatures.
If you only have time for one thing, make it a scenic drive through the iconic Tuscan countryside.
Begin by visiting one of the most beautifully intact historic towns in Tuscany: Siena. Start the day at the city’s Gothic cathedral to admire works by Donatello, Michelangelo, and Bernini. Then, take a deep dive into the city’s medieval center to admire the Piazza del Campo, home to the Palazzo Pubblico and Torre del Mangia, and the Basilica di San Domenico.
In the afternoon, strike out through the surrounding countryside to savor some of the most unforgettable vistas in Tuscany—the rolling landscape of Crete Senesi and the woodlands of Val d’Orcia—and pop into picturesque towns like Pienza, Montepulciano, and Montalcino.
This morning, meander through the sleepy hill towns that bear the area’s name—Greve in Chianti, Panzano in Chianti, Radda in Chianti, and Castellina in Chianti. Stroll through their medieval centers to admire historic churches, picture-perfect piazzas, and sweeping views over the surrounding hills.
In the afternoon, sample some of Tuscany’s top wines at local cellars and join a hands-on cooking class to learn to prepare classic Tuscan dishes.
From Chianti, travel to San Gimignano to see highlights like the city’s 14 historic towers, the Collegiate Church of Santa Maria Assunta, and Piazza Duomo, before tucking into a Tuscan dinner.
On your final day, travel to one of Tuscany’s headliners: the Leaning Tower of Pisa. Begin your day by delving into Pisa’s historic center. Once the morning tower crowds have thinned, join an afternoon tour that includes skip-the-line tickets to take in the spectacular Piazza dei Miracoli, a UNESCO World Heritage Site that includes the Gothic Duomo and Leaning Tower, among other sights.
End your day in the much less crowded town of Lucca. Take a walking or biking tour of the highlights in the historic center before capping off the day with an evening stroll (passeggiata) along Via Fillungo.
