Beyond the Bit

Il Palio di Siena: the Oldest (and Rowdiest) Horse Race in the World

04.15.16 | Preferred Properties, World Events

Il Palio di Siena is a horse race with a long pedigree — it dates back to the Renaissance. Predating the existence of the Thoroughbred as a recognized breed, this raucous and rowdy free-for-all is possibly the most exciting horse race in the world!

il palio di siena

Il Palio di Siena: an Exhilarating Equestrian Experience

Taking place every July 2 and August 16, and resembling roller derby more than the Kentucky Derby, this unique race encourages the bareback riders to upend their competitors (using their whips if necessary!) and win by any means necessary. Of course, unseating your opponents won’t guarantee you a win. The horses are considered the real stars of the race and they don’t need a jockey to win — they just need to complete the three laps and be first across the finish line.

Each horse represents a contrada, one of the medieval city’s 17 districts. The fierce competition between the rival contrade continues even after the race. Parties celebrating the crushing defeats of other contrade continue for a month after the last horse crosses the finish line! As guests of the Rosewood Castiglion del Bosco, one of Journeys’ preferred properties, you’ll enjoy a private tour of Siena — including some of the best parties.

There’s no need to stand crammed shoulder to shoulder in the middle of the course while horses attempt to negotiate the 90 degree turns on the makeshift track in the Piazza del Campo. Instead, you’ll enjoy private seating above the piazza for the pre-race Corteo Storico costume parade with its percussion performances, swirling flags, and traditionally costumed contrade. Enjoy delicious catering and fine Italian wine during and after the exhilarating race.

As participants in the Castiglion del Bosco Palio Package, you’ll also have access to the training runs and qualifying races before the big day and enjoy a gourmet dinner in the piazza to celebrate the event.

Get the Best of Tuscany at Castiglion del Bosco

il palio di siena castiglion del bosco
Villa Sant’Anna, one of Castiglion del Bosco’s stunning accommodations.

The Rosewood Castiglion del Bosco is a wonderful place from which to experience the beautiful surroundings and authentic Italian culture of this World Heritage Site. Located on an 800-year-old estate, the resort features 5,000 acres complete with castle ruins, a medieval church, and a charming, historic village. More modern amenities include a spa, carefully selected excursions and activities, and Italy’s only private golf club.

A culinary destination in its own right, the resort features a prominent winery, two restaurants, its own organic vegetable garden, and a cooking school where you can learn how to cook some delicious Tuscan cuisine.

Located within the village, the 23 suites offer antique charm coupled with the latest in modern comfort and technology. There are also ten luxury villas housed within restored farmhouses dating back to the 17th and 18th centuries. These three to six bedroom villas also offer heated pools. Some even feature a home theater or private tennis court.

Contact us for more information on how you can enjoy this wild ride amidst the beautiful Tuscan surroundings.


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