• Mike DiCarlo

Siena - The Puzzle Unwound

Updated: Jul 10, 2019

Siena is arguably Italy’s most beautifully preserved medieval city. It is built on three hills and you should expect steep walks down ancient vicoli surrounded by massive buildings. It’s one of the first things we noticed when we arrived. All of Siena’s structures are bigger than any others that we have encountered in a city its size in Italy. It seems all of Siena’s buildings are imposing whether it’s the local tourist office, the buildings in the piazza del Campo (the heartbeat of Siena and its main square), or the Gothic beauty, The Duomo. We were told that that the original plan was for a much larger Cathedral and while hard to imagine, all one needs to do is turn a corner to see the original nave which is also enormous!



All of this is puzzling as Siena is considered to be a small city with a population of 54,000. But in medieval times Siena was a noble city and the most powerful banking city on the Continent. This little piece of information will give you context to unravel the Siena puzzle when you visit the city.


We missed by a week the ancient horse race, the Palio, that is run three times around its main square, Piazza del Campo. The race is run once in July and once in August. Preparations were underway and the pride of the Sienese was palpable. Every neighborhood, the contradas (there are 17 of them), sponsors a horse and rider. The competition is fierce with all types of machinations happening behind the scenes. It’s amusing to walk down the street and see the banners on both sides clearly demarcating contrada loyalties.

We stayed at the Residenza d’Epocha Palazzo Borghesi. The name suggests elegance and it truly delivers with old world charm. While small in size, it is only 4 Italianate rooms, the location is superb. You are a 3 minute walk to the Duomo and countless places to eat and drink. As an aside, our room showcased the most beautiful city view we had ever experienced in a hotel.


We are 16 days into our 25 day tour of Northern Italy and we had our very best meal, hands down, in Siena. The Taverna di San Giuseppe has it all. Wonderfully simple but well executed food, friendly and attentive service, and an outstanding ambiance. The wine and cheese cellar dates from approximately 200 B.C. and the main dining room is a 14th century stunner. We highly recommend this restaurant. If you’re in Siena, put San Giuseppe on your list.

Two days were hardly enough for us to see all that Siena has to offer but it was enough time to begin to understand that tradition is very important to this city. The contradas may compete twice annually in their Palio but they do so only in the name of tradition. Competition and bragging rights play a much smaller role. If you plan to visit the Florence area, Siena is a wonderful stop along the way and if you make it in July & August, you’ll have a horse race to watch!


Post script: After visiting Florence, I know a lot more about Siena and their bitter rivalry. Ultimately, Siena lost its preeminence to Florence. The Sienese were partly to blame because of the infighting within the contradas but Florence's noble families and their unprecedented wealth and influence made them a formidable adversary.

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