Festivals & Unique Events

Il Palio di Siena is one of the most colorful and unique horse races in the world.  Held every summer on July 2 and August 16, the race is run by bareback riders around the beautiful main piazza – the Campo – of Siena.  The Palio has for centuries been the focal point of the intense rivalries among the 17 contrade (wards) of Siena, with 10 of them chosen to compete in each race.  Although the race itself lasts only 90 seconds or so, the pageantry and festivities leading up to the race last for days, with parades through the streets, practices by the drummers and flag throwers of each contrade, practice runs the day before the race, and the magical contrade dinners the night before the race that take place on huge long tables set up in the streets.

Also worth visiting are the contrade museums, which display the banners – the “palios”, for which the race is named – won over the centuries.  So even if you don’t attend the race itself, being in Siena in the weeks leading up to the race is one of the most special moments you’ll have in Italy.

L’Eroica (translated as “the Heroes”) takes place in Gaiole the first weekend of October each year.  It is not a bike race, but rather a non-competitive biking event that celebrates three key things: the return to the authentic roots of cycling by allowing only pre-1987 bikes to be ridden; the social aspect of cycling; and the protection and preservation of the historic white (gravel) roads of Tuscany known as le strade bianche. At least 50% of each of the five routes – which range from 46km to 209km – are on the Tuscan white roads. The two longest routes are ridden on Saturday with the riders starting pre-dawn. (Pre-1930 bikes start at 4:30am!) The remaining three routes are ridden on Sunday. Depending on the route, riders can be “in the saddle” over 13 hours. The event’s slogan: “The beauty of fatigue and the thrill of conquest” is very fitting! On both Saturday and Sunday nights the main square of Gaiole is closed for a huge party as the riders cross the finish line and celebrate their achievement with fellow riders, family and friends.

In 1997, in reaction to the scandals rocking professional cycling, Giancarlo Brocci, a resident of Gaiole, decided to organize a cycling event for his friends that emphasized classic (i.e., pre-1987) bikes and riding on “le strade bianche”.  That event has evolved into L’Eroica which is the most important classic biking event in the world and has spawned similar events in California, Japan, South Africa, Spain, Germany, the Netherlands and the UK, as well as other locations in Italy.  These other events are called just “Eroica”, not “L’Eroica”, as this title is reserved for the original Gaiole event. Every year, L’Eroica draws 9,000 riders and countless fans to our little town.

The atmosphere in Gaiole leading up to the event is fantastic. There is a huge marketplace of vendors selling every kind of cycling gear imaginable, pop-up food vendors and all the restaurants and cafes adding extra seating, even a specialist barber set up outdoors to make sure the riders look as stylishly antique as their bikes. Gaiole has two year-round L’Eroica shops: the original, an independent shop in the center of town (one of the best designed retail spaces we have seen) and the second, a big corporate-owned shop, with more riding gear and L’Eroica souvenirs. 

Not far from Gaiole, there is a year-round Eroica Cafe, across from Castello di Brolio’s wine shop. It is a perfect place to take a break and enjoy a coffee and pastry or panini lunch or late afternoon Aperol Spritz or glass of wine while watching touring bikers go by. On the day of L’Eroica, all the riders, no matter which course they are taking, traverse the winding road leading up to Castello di Brolio at the start of their journey. Approaching the historic castle in the early hours of the morning, when the road is lit only by lanterns, is one of the most extraordinary and memorable experiences of the ride. Even if you don’t bike, L’Eroica is truly an event not to be missed.  www.eroicagaiole.com

The stunning Tuscan hilltop town of Certaldo Alto – reached by a funicular railway – hosts the Mercantia in mid-July each year over five days. It is the most important international Italian street theatre festival in the world. With over 80 shows every day, the squares and streets of this medieval town overflow with 100s of artists – theater troupes, street artists, contemporary art, artisans, installations, and lots of people!  The festival runs from early in the day to very late in the evening – our favorite time to go is at night – and presents an astounding variety of performers and artists. Our most memorable performance was the dance troupe that performed on the castle’s walls suspended more than 30 feet in the air.  Apart from the official program, in the true spirit of street theatre, there are informal performances that pop up in every nook and cranny of the town.  The festival is very popular, but the crowds are all part of what is a really unique event. www.mercantiacertaldo.it.

This weekend-long wine festival featuring more than thirty Raddese wine producers. More than 80 wines are available for tasting. Buy your own glass (which you get to keep) complete with a goblet carrying strap, and sample as many of the wines as you would like while you talk to the vintners who make them.

On the first Sunday of every month of the year (and the proceeding Saturday), rain or shine, there is a remarkable antique market in the medieval town of Arrezo.  The variety of wares is astounding, the setting is magical, and if you are like us, you will enjoy the hunt to bring home the perfect one-of-a kind souvenir. Arezzo is one of twelve Estruscan cities conquered by the Romans and its street are filled with history, art and shops. Note: We sourced many of the antique furnishings for L’Aiaccia at this market.