10 Stunning Photos That Will Make You Want to Visit Siena, Italy

It’s no secret that perhaps my favorite trip ever was a road trip through Italy that I did with my sister. Italy is one of those countries that seemed to have a bit of it all: quiet and quaint coastal towns, villages that transport you back hundreds of years, majestic castles literally popping out of the landscape around every turn, epic hikes, and beautiful cities. 

And what better way to see the countryside in Italy than by renting a tiny little Fiat for 10 days? And then driving said car down a path through the middle of a hayfield that Google maps tells you is a road. I had my doubts, but we made it! My favorite part of the whole trip though was our spontaneous trip to Siena. Why this place wasn’t higher on our list, I will never understand! Make sure you don’t make the same mistake and plan for plenty of time in this little Italian gem!

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Siena is the most gorgeous town that fell straight out of a medieval storybook. And don’t just take my word for it, UNESCO named Siena the ‘ideal embodiment of a medieval city’. Plenty of parking is available outside the city walls, which is where I would recommend leaving your vehicle. Enter through the Porta Ovile entrance and just wandered around until we came to the Piazza del Campo. There is a saying in Siena that all roads lead to the Piazza del Campo, so it isn’t so easy to get lost if you orientate yourself to the Piazza, despite the winding city streets.

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We also just so happened to be visiting Siena during the Palio de Siena, Siena’s famous horse race held twice a year on July 2 and August 16. During each race 10 of the 17 contradas race horses bareback around the Piazza three times, with the whole race lasting less than 90 seconds. Huge crowds gather under the hot sun for this event and there is a lot of fanfare leading up to it, including a parade with each contrada dressed in medieval costumes and their own colors. Despite the size of the crowds that gather for this event, the Piazza has plenty of room!

If you happen to be visiting Siena during the Palio I suggest buying your favorite contrada’s flag (either based on which contrada you like or, if you’re like me, based on which flag design you like best). It’s fun to be able to wave the flag in the air and cheer for a particular horse, it makes you feel like part of the festivities. Vendors sell these all over the city during race day so it’s quite easy to grab one and then you have a souvenir to take home as well!

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The Piazza was designed to be large enough to hold the entire population of Siena (which, before the black plague, was the same size as Paris) for activities, games, and political events. Today the Piazza holds horse races, events for Carnival, and special nighttime events held under the stars. The Piazza is also a great spot to hang out eating your gelato after walking through the romantic streets and strolling through the plethora of museums the city offers.

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Another stop on your tour of Siena should be the Piazza del Duomo. The Duomo (or the Cathedral of Saint Mary of the Assumption) of Siena dominates this square. The gorgeous cathedral was begun in 1230, but received a transformation in the 1300’s and artists worked on the cathedral throughout the 1400’s. The cathedral also features the Libreria Piccolomini which was built to store the collection of books belonging to pope Pio II Piccolomini.

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The Piazza del Duomo is also famous for the tall column with a statue of a she-wolf suckling Romulus and Remus. The legends state that Siena was founded by the sons of Remus, Senius and Aschius, when they fled Rome after Romulus killed Remus, fearing for their lives. The sons stole a statue of the she-wolf from Apollo’s Temple during their flight and the she-wolf became a symbol of their new city, as well as a reminder of their origins. Aside from the column in cathedral square you will see statues and references to the she-wolf throughout the city.

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While I only got to be in Siena for one day I know I will be back to visit this city and explore more of its winding streets very soon. Have you visited this city before? Let me know your thoughts!