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.

The Plaza de San Pablo is among the most important historical sights of Valladolid. Felipe II was born in the Palacio de Pimentel on the Plaza de San Pablo in 1527, and as testimony, a fabulous tiled mural relates the life of the king and the history of sixteenth-century Valladolid. In the square is also the magnificent Iglesia de San Pablo located.

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.

Darat Al Funun unites contemporary Arab art with layered history. Housed in a gracefully restored 1920s complex, its rotating exhibitions unfold alongside Byzantine ruins, including a 6th-century church at the entrance. The hillside gardens frame panoramic views of Amman, making this as much an architectural pilgrimage as an art destination.