Tuscany

The Leaning Tower of Pisa is one of Italy’s (and the world’s) most recognisable landmarks—but the tilt that made it famous wasn’t part of the plan. Construction started in the 12th century, and the soft ground caused it to lean almost from the beginning. Up close, it’s oddly striking, almost like a lopsided wedding cake, and yes, you can still climb it.

Siena still runs on medieval time—in the best way. Its centre hasn’t changed much in centuries, and that’s part of the charm. The Piazza del Campo is the heart of it all—it’s where the Palio horse race happens twice a year. Climb the Torre del Mangia for wide views across the rooftops. The cathedral’s worth the time, especially its black-and-white striped interior, detailed floor mosaics (open seasonally), and the Piccolomini Library tucked inside. Don’t skip the crypt or the Museo dell’Opera del Duomo—they’re quieter and give you a different angle on the city.

Val d’Orcia conjures up everything you picture when you think of Tuscany—rolling hills, cypress-lined roads, and quiet hill towns. It’s a protected UNESCO site, partly because of the landscape, partly because of how little it’s changed over the centuries. Pienza is the standout—it was designed as the 'ideal city' during the Renaissance and still feels unusually well put together. The Abbey of Sant’Antimo is a peaceful stop, tucked into the countryside. And if you're into wine, this is Brunello country—some of the best reds in Italy. Even just driving through is half the experience.

Best known for Michelangelo’s David, this gallery is a must for anyone interested in Italian art, from Renaissance sculpture to paintings and even some old musical instruments. Besides David, you’ll find works by Botticelli, Ghirlandaio, Pontormo, and others.

This masterpiece of Italian Gothic architecture is most famous for what it’s missing—a roof. The abbey was built in the late 1100s and has been a dramatic-looking ruin for centuries. It’s open to the sky now, but still feels grand in a stripped-back kind of way. Just up the hill, the Rotonda di Montesiepi is worth a quick stop too—inside you’ll find a sword embedded in stone, tied to the story of Saint Galgano.

Tucked into the hillside just outside Cortona, Le Celle is a small Franciscan hermitage dating back to the 13th century. It’s peaceful, simple, and still run by monks today. Saint Francis stayed here briefly, and you can actually see his old cell. The hermitage is a sight in itself, but also benefits from beautiful surroundings.

Behind the Basilica di San Lorenzo, the Medici Chapels are a major stop for anyone interested in Florence’s history. Built to honour the Medici family—patrons, rulers, and power players—the chapels hold some of the most impressive tombs in the city. The Sagrestia Nuova (New Sacristy), designed by Michelangelo in the 16th century, is the standout, mixing sculpture, architecture, and a fair bit of Medici pride.

Florence wasn’t just the Medici’s playground—the Strozzi family had their own share of power, and this palace was built to prove it. Filippo Strozzi the Elder commissioned it to show up the Medici and make a statement about his family’s status. These days, the Renaissance palace hosts rotating international art exhibitions and cultural events, and it’s one of the city’s top spots for contemporary shows in a historic setting.