Nestled in the heart of one of the most well-known regions of Italy—Tuscany—sits Siena, the capital of the eponymous province it is a part of. With a historic center that has been deemed a World Heritage Site and a history dating back over the centuries, this is one of the most Italian cities you could ever hope to visit while in the country. An independent city-state during the Middle Ages, Siena has its very own distinct culture and flair that is both like and unlike what the average person thinks an Italian city should have. For sheer authenticity, there is no better city.
The overall architectural feel in Siena is decidedly Gothic, and the city has a fierce rivalry with Florence, a characteristic that has been part of the people’s provincial pride ever since the city suffered defeat at the hands of the Florentines in 1555. This is one of the few places in Italy where you can see physical remnants of the old ways, especially in such events as the Palio, which is a horse race held twice every year in July and August. More than just a simple race, the event is the lifeblood of Siena. The days leading up to the race are filled with passionate trash-talking between contestants, with neighborhood rivalries often turning violent. The race itself takes place in the beautiful and majestic Piazza Del Campo, and visitors also have access to such sights as the Cathedral, the Church of San Domenico, and the Piazza Salimbeni.
Siena also has a unique social structure in the city, with it being divided into districts, each with their own flags and mottos and each with their own stories and personalities as well (apparently the Goose district has some arrogant people). These little communities are so endearing, I suggest you choose the one best suited for you and get the flag of that district to take home with you. Along with the districts comes the horse races. If you get the chance in June, you should come to experience them. No holds bar horse racing around the square...all for the pride of the district. There are colors, flags and traditional garb everywhere.
While it’s true that it’s not as flashy or fancy as Rome or Florence or any of the other major attractions, part of Siena’s charm is in the fact that it’s not a major destination, but a reserved city in the heart of Italy, waiting to be discovered.