Tuscany (Florence, Siena, Chianti)

Tuscany is often the idealized image of Italy, and it works wonderfully for families if you balance art with activity. Florence (Firenze) is the cradle of the Renaissance. While museums like the Uffizi can be tiring for kids, many offer family tours or scavenger hunts. A great alternative is the Leonardo da Vinci Interactive Museum, where kids can touch and operate machines based on his designs. Climbing the 463 steps of Brunelleschi’s Dome is a physical challenge with a rewarding view.

Outside the capital, Pisa is an essential stop. The Leaning Tower is smaller than many expect but incredibly fun to photograph and climb (age restrictions apply). Nearby Lucca is perhaps the most family-friendly town in Tuscany; its broad, tree-lined renaissance walls are completely closed to traffic, creating a 4km loop perfect for renting bikes and cycling with children.

The countryside is best experienced by staying at an agriturismo (farm stay). In the Chianti or Val d'Orcia regions, these stone farmhouses usually have swimming pools and offer plenty of outdoor space for kids to run free while parents enjoy the local wine. San Gimignano, known as the "Medieval Manhattan" for its stone towers, captures the imagination, and is famous for having some of the world's best gelato at Gelateria Dondoli in the main square.

For a gothic twist, the Abbey of San Galgano is a roofless church with a real "sword in the stone" nearby at the Rotonda di Montesiepi—a direct link to Arthurian-style legends. Tuscany is hilly, so expect plenty of walking. The food—steaks, bean soups, and pasta with wild boar—is hearty and generally well-received by children.