If you step back into the Renaissance as you visit Florence, then Siena takes you back into the Middle Ages. The city center sits on several hills so expect some climbing but it is quite small and the main sights are close: start in the Piazza del Campo, famous for its particular shell shape and for the Palio of Siena, a horse race between the various parts of town run twice every summer on July 2 and August 16. The Palazzo Comunale and Torre del Mangia tower over the Campo, offering an impressive view of the square and the city if you climb all the way to the top.
Head to the Duomo, standing majestically as a precious example of Italian Romanesque-Gothic style and admire the scenes across its pavement, a treasure waiting to be admired! Head back out to visit the Baptistery, crypt and Opera museum to see Duccio Buoninsegna’s marvelous Maestà alterpiece from the 14th century. .
Just outside of Siena, the charming walled castle of Monteriggioni offers another trip into medieval times. The small castle still stands with 15 towers along the walls (although some of them were cut short through the centuries). You can visit the small castle, but don’t forget to climb and walk along the massive walls from where you’ll admire great views over the Tuscan countryside.