Sienna

Located roughly an hour outside of Florence, Siena is one of my favorite places in Italy. When you think gothic architecture and medieval town, you think of Siena. Built as a fortified city behind large, thick walls on a small mountain, Siena oozes history. Cars are barred from much of the city, so you can meander down ancient brick alleyways below towering wall-to-wall residences.

In Siena, you’ll find a relaxed way of life, two music schools and just a general feel of what Italy must have been like in the past. Head to the Piazza del Campo in the heart of the city and grab a seat in a café. As you gaze across the city, you can view the Duomo Cathedral that towers over the city. Unlike other cities, the cathedral does not contrast with the buildings around it. All of Siena retains the gothic medieval architectural style and you’ll be hard pressed to find a better gothic example in Europe.

The best way to experience Siena is to simply stay there. Like wine, Siena improves the longer you stay. Daily explorations lead to surprising little shops, incredibly friendly people and a general feeling of peace.

Il Palio

If you prefer a little action on your trip, Siena has an event that rivals any in Europe. The Il Palio bareback horse race around the Piazza del Campo is a sight to be seen. The fun starts well before the race when various neighborhoods challenge each other. The challenge comes in the form of bands walking through “enemy" neighborhoods in the middle of the night and making an unholy racket. Eventually, each neighborhood produces a horse and rider for the day of the race. Bareback, the riders race for neighborhood pride among an absolutely screaming crowd of people. The running of the bulls has nothing on this event.

If you visit Florence while in Italy, take the time to spend a couple days in Siena. In fact, blow past Florence and go immediately to Siena.