Things to do in  Tuscany

That iconic photo of Italy you’ve seen—the one of a cypress-lined country lane zigzagging its way toward a hilltop villa through vineyards, olive trees, and sunflower fields—was snapped in Tuscany. This region is known for its postcard-perfect landscapes sprinkled with medieval villages, storied wineries, and Renaissance estates.

Tuscany is a sprawling region, home to both Florence and Pisa. Spend at least three days to touch on the most famous towns and villages of Chianti and Val d’Orcia. To take in Florence’s Renaissance treasures and the Leaning Tower of Pisa, you’ll need at least two more days.

Vineyards cover much of Tuscany, and the region produces a number of Italy’s most prestigious wines. Headliners include Chianti Classico, Brunello di Montalcino, nobile di Montepulciano, and Vernaccia di San Gimignano produced in the hills of Chianti and the Val d’Orcia, as well as the coastal Bolgheri reds.

Not necessarily. Agriturismo (farm holiday) stays, casual trattoria meals, and tours of the smaller hill towns are ideal for budget travelers who are keeping their eye on the bottom line. Those looking to splurge can choose luxury wine estates, Michelin-starred restaurants, and the elegant city of Florence for sightseeing.

Tuscany has a collection of delightful hilltop towns to visit, all of which offer historic cityscapes and scenic views. Top options include San Gimignano, Montepulciano, Montalcino, Pienza, Pitigliano, Arezzo, and Cortona; the larger towns of Siena and Lucca are also known for their elegant historic centers.

Siena is the best option for a small town that offers A-list sights, dining, and shopping—plus convenient train connections. For a village atmosphere, Pienza is a great choice, though its lack of a train station makes getting around a challenge. City slickers should opt for Florence, Tuscany’s capital and transport hub.