32 Enchanting Medieval Towns That Feel Frozen in Time

30. Siena, Italy

Often overshadowed by Florence, Siena is a medieval masterpiece that rivals its Tuscan neighbor in beauty and history. Its iconic Piazza del Campo, the shell-shaped main public space, is where the thrilling Palio horse race still takes place twice a year, as it has since medieval times. The city is a labyrinth of narrow, winding streets, grand Gothic palaces, and the stunning Siena Cathedral. Its preservation and vibrant medieval traditions make it an immersive step back into a proud and powerful past.