Contrary to popular belief, all roads do not lead to Rome. However, many roads DO lead to Siena. Now, we are familiar enough with Italy to know that we’ve seen some exceptional piazzas, those huge main market squares that anchor a town and provide numerous opportunities for people watching to weary tourists.

Some of our favorites include Marostica, where they have a huge chessboard in marble right in the middle of the square and once a year players on horseback actually get together to play a rousing game of chess;

and St Mark’s Square in Venice where an empty space was instantly swarmed with pigeons when we brought out a speck of food that practically lifted Lauren up into the skies.

And don’t forget St Peter’s Square in Rome where Lilly exlaimed, “This is not a square. It’s really more like a squashed circle.

You can imagine our lackluster enthusiasm for walking from the car to the main square of Siena. We were expecting another ho-hum space filled with hungry tourists and sky-high sandwich prices. And, parking our car on the very outer edges of the city to avoid paying for parking only meant it was going to be a long walk for dinner which prompted very hungry children to say, can’t we just stop NOW and eat? But I persisted in following the signs to the “Dom” and we were rewarded with one of the most spectacular evening views we’ve ever had in Italy.

I simply looked at Lindsey and said, “This is pretty good.” Actually, I was awestruck at the immensity of the square and it’s perfect proportion to the buildings around it. Best known for the annual Palio, a horse race held inside the square where the seventeen town neighborhoods (known as the contrade) vie for the “palio” a big drape of precious fabric painted by a talented local artist, Siena is an Italian dream. Set on a hill, the colors of the buildings as well as the brickwork have that subtle burnt umber glow that a Tuscan sun warms to a nice glow. The main cathedral reminded me of the one in Florence with a great black and white facade and rich geometric patterns throughout the interior. There are numerous twisty side alleys that are chock full of souvenirs including pottery featuring the symbols of the different neighborhoods. One of my favorite symbols was for the Tower neighborhood (Torre) with an elephant carrying a tower on his back. It is the only neighborhood to have two enemy neighborhoods. I can only imagine the years of story development that the Sienese have engaged in to keep the rivalry alive.
In the end, we visited Siena 4 times during our holiday. Not only was it rich in history, every road did indeed seem to lead to Siena.