Best Festivals in Tuscany
Credit: Michael Freeman/Corbis

Tuscans’ love of food, wine, and good company culminates in that revered yearly event: the festival. The smallest town has one, mostly focused on a patron saint or a food, often both. In the smallest towns like Camigliano, population 32, the entire town gets together and cooks up a three-day storm centered around galletto (little rooster). Others, like San Giovanni D’Asso, hold feasts about truffles, wild boar, frogs, geese, or olive oil. In all of them are huge tables set with sumptuous Tuscan feasts. In larger towns and cities, the festivals are grander and each unique: Il Palio, the horse race in the vast town square of Siena, the international festival of arts—music, theater, dance—in Montepulciano, or the regatta and lights festival in Pisa. Tuscans take these festivals to heart. Most are accompanied by magnificent, centuries-old costumes and pageants. An entire town can slip two-thousand years back in time, like the Presepe Vivente, in the medieval town of Castel del Piano, when for a week around Christmas, only bonfires and candles light the ancient walls at night, and everyone is dressed à la Bethlehem. The streets and cellars are full of blacksmiths shoeing donkeys, bakers baking bread, and vintners boiling spiced wine under the stars, in the snow.

Il Palio (Siena)

Twice each summer, July 2nd and August 16th, Siena undergoes a miraculous transformation. The town is festooned in medieval splendor of the seventeen districts, each with its own color and design of costumes, crest of arms and flags. Its remarkable town square, Piazza Del Campo—actually a brilliantly designed and very beautiful thirteenth-century concave fan, paved with brick, constructed to gather rainwater for the town’s wells—is converted, thanks to countless truckloads of sand, into a crowd-packed horse racetrack. But the crowd is in the middle, and the horses race around the crowds, under the walls and balconies. Not to be missed for the medieval pageantry, excitement, and the sight of grown men crying because the horse (sometimes rider-less) from their district wins or loses the race. Don’t ask how it works—there are mystifying bets and switches and intrigue. Just go and enjoy.

Luminara and Regatta in Pisa

Since 1688, every 16th and 17th of June, Pisa stops and celebrates. The 16th is the eve of the city’s patron saint San Ranieri. Through the night, on both banks of the Arno River that traverses the city, more than 70,000 tiny oil or wax lamps are lit on the façades of buildings and towers. The magic is multiplied by their flames reflecting upon the gently moving waters. To heighten the romance, thousands of candles are lit and set afloat on the river. If that wasn’t enchanting enough, at 11 p.m., there are fireworks. The next day is the mile-long regatta: four long rowboats—one from each historical quarter—with eight oarsman in each, festooned in their own colors, race upstream. In typical Italian fashion, it is not the first arrival that wins, but which headman is first to clamber up thirty feet of rope to furl a banner.

Explosion of the Cart (Florence)

Okay, so this is no cerebral event but colorful and noisy and fun. Dating back centuries of Easter Sunday mornings, a street procession of flag throwers and drummers in historical costume lead a cart, three stories high, drawn by white oxen through the streets of Florence. They are followed by priests, bishops, and other celebs. The climax comes at the end when upon arriving in Piazza del Duomo, the structure atop the cart is set ablaze with fireworks. It’s a tradition that goes back to the Crusades, although fireworks were only added in the 14th century. This is no idle event since a successful execution is said to bring a good harvest.

Volterra A.D. 1398 Medieval Festival

Every third and fourth Sunday of August, Volterra in the province of Pisa, steps back eight centuries. The streets and piazzas throng day and night with war horses, armored knights, crossbowmen, jesters, musicians, dancers, falconers, flag wavers, monks, peasants and buxom ladies. Ancient craftsman’s stalls blend with tables set with of medieval foods. Meanwhile the nearby serene Parco Archeologico comes to boisterous animation with the recreation of classical country life. A village with its shepherds, friars, soldiers and flocks and herds of domestic animals, mill about fires cooking savory classic dishes. And of course there are special events for kids: learning archery, jousting and fencing. A must for kids of all ages.

Cantiere Internazionale d’Arte di Montepulcino

This is the best art festival in Tuscany. For the past thirty-eight years, the summer evenings and nights of Montepulciano have come alive with song, music, theater, and dance. The program is wide-ranging: from classical to avant-garde with many world debuts. The venues are performed in the most intriguing locations: churches, courtyards, squares, and buildings. Magical, in the balmy Tuscan nights when the theatrically lit surroundings of this dramatic hill town, greatly add to the effect of the performances.