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Siena & Montepulciano

Writer: Sheri Graciano
Sheri Graciano
Jul 8, 2010
4 min read

Updated: Jun 25

After spending our first full day in Cortona lounging by the pool and making new friends we ventured out to Siena on our second day. GPS in hand – because I’m not sure we could ever find our way back here without one – we arrived in just over an hour.


Il Palio had taken place three days prior. A bit of history on the event for your reading pleasure:

“Piazza del Campo” is still used today for the well known Palio horse race which is one of the most famous popular Italian manifestations. It takes place every year on July 2 and August 16. The Palio is run to celebrate the miraculous apparition of the Virgin Mary near the old houses that belonged to Provenzano Salvani. The holy apparition was therefore called “Madonna di Provenzano” in whose honour the very first Palio was run on August 16, 1656. The Palio was run for the first time in 1701 in honour of the “Madonna dell’Assunta” the patroness and Advocate of Siena through all the tragic events since she protected the Sienese militia at the famous battle of Monteaperti on September 4, 1260, against the Florentines.


The Palio is a historical secular tradition strictly connected with the origin of the Contradas of Siena (districts into which the town is divided). The Contradas are spectacular agonistic institutions each having their own government, oratory, coat of arms, appellations, sometimes titles of nobility, emblems and colours, official representatives, festivities, patron Saints, with protectors, delimited territories and population which consist of all those people who were born or live within the limits of the district. For those of us exploring Siena, if we simply look up while walking we can easily tell when we've crossed into a different contrad simply by looking at the ornate street lamps as each contrada has its own design. At one time there were more than 50 contradas however now only 17, ten of which participate in il Palio.


The night before the big horse race around the piazza each Contrada lines the streets with tables and hosts a huge feast. Unfortunately we didn’t learn about this until we met Tania and Keith (who attended) else we would have made reservations and would have most certainly gone! We did think for a moment of attending Il Palio itself but the enormous crowds are just too much for trying to hang on to two small children. In the meantime, attending the feast the night before has certainly been added to my bucket list!


Our day in Siena was fabulous … good food, cold gelato, and the four boys climbed to the top of the civic tower while the girls shopped! I was enamored with the beautiful street lights which signified each Contrada and want to get back to Siena when the kids are a bit older so that I can take photos of all of them.

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On Tuesday Lance and Kris got up and out of the house early and ventured off for a day of wine tasting in Montepulciano while Hugh and I stayed behind with the kids. They came home in the early afternoon and we traded, with Hugh and I spending the afternoon and evening doing the same.


On the way there we happened upon the area of Gracciano, a small town within the Montepulciano area. Once arriving in the city of Montepulciano, we learned the main street is also called Via Gracciano! We felt like royalty!

There are many quaint shops in Montepulciano offering wine, cheese and olive oil tasting as well as self guided tours of their amazing, large, and very old underground cellars.


At our second or third stop we met Angelo at Vini di Toscana, who spoke fabulous English and treated us to a wealth of information about the local wines, none of which I retained. While stopping at the register to get information about shipping wine to the states I noticed he had a book with photos of Il Bravio delle Botti, otherwise known as barrel races. Evidently races of some sort between contradas is a very popular pass time in many Tuscan villages! Here in Montepulciano the eight contradas (one of which is Gracciano) compete by racing a large wine barrel full of water uphill. Though the race takes mere minutes to complete, the festivities building up to the race last days before. Angelo shared with us that his Contrada came in 2nd place two years ago and proudly pointed at a flag hanging from the ceiling while explaining that he’s from the Gracciano Contrada.

When we inquired where we might get such a Gracciano flag Angelo informed us that they aren’t for sale and that only the group that organizes the barrel raced have access to the flags. He offered to inquire about getting us one from that group, and when we walked back by his store a few hours later he informed us that he would likely have a flag for us tomorrow.Long story longer … he did, and we are now the proud owners of a Gracciano Contrada flag that actually flew during the barrel races last August. What we will do with it is anyone’s guess, but it provides us with a great memory so it really doesn’t matter!



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