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The Palio di Siena

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Attend a Medieval Horserace!

We can host your group for this unique experience of attending the Palio di Siena horse race as the focus. Use our itinerary below or we can help you build a personalised one.
The Palio di Siena horse race is celebrated twice a year in the Campo (Siena’s historical square), on 2nd July and 16th August in honour of the religious feast days of the Visitation and Assumption of the Virgin Mary, Lady and Patron Protector of the City. It has been held almost uninterrupted since the days of the medieval Republic of Siena. Preceded by a colourful procession of historic pageantry with traditional orders, costumes, drummers and flag throwers represented, to experience the Palio is like watching ritualised warfare, in which the jockeys are the mercenaries.

Arrive a few days beforehand to breathe-in the Palio atmosphere – remember that it is not a festival for tourists but an important moment in the life of the Sienese where spectators are welcome. Ask as many questions as you want but try not to express opinions. Palio di Siena preparations begin in the Campo of Siena. All conversation among members of the ten competing districts or Contradas is concentrated on two topics: which horse will we draw – who will ride it?

The Horses are selected and allocated by lot just three days before the race, must run bareback and there are only six trials beforehand. The responsibility for choosing and paying a jockey lies with the individual Contrada. The line-up is drawn by ballot and the race starts when the horses are lined up correctly and the Starter drops a rope. Victory is granted to the Contrada whose horse having completed three turns of the course, arrives first past the finishing flag, even if the jockey has fallen off!

Country:  Italy

Region:  Tuscany

Capital:  Florence

Area:  23,000 km/sq

Population:  3, 750,000

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Day 1


We meet between 14.00 and 16.00 at the Terontola train station, easily reached from Rome, Milan or Florence. Relax and settle in for the week. Enjoy a welcome cocktail party and dinner and watch an introductory video of Il Palio.

Day 2

Etruscan Cortona

We climb through olive groves to arrive at Hannibal’s Point with stunning views of Lake Trasimeno and Cortona. Then continue along Hannibal’s trail to reach the exquisite romanesque church of Sepoltagli. After a picnic lunch under the shade of umbrella pines we descend to the sleepy village of Ossaia (derived from bones) so named after the 217b.c. Battle of Trasimeno between the Carthaginians and Roman legions. Then time to relax, unwind and dip in the pool. The afternoon brings a guided tour of Cortona’s Etruscan museum with time before dinner to enjoy Cortona’s cafes and boutiques. (4hrs/12km)

Day 3


Gubbio is a medieval gem built of warm pink stone, dating back at least as far as the Umbrians who preceded the Etruscans. We travel through the Umbrian countryside and along the Tiber valley to Gubbio where a walk with stunning views beckons us. After a picnic lunch a visit to the church of St. Ubaldo, perched on the edge of the hillside and inside the relic of the saint himself. We descend by cable car to explore the medieval town, admire the local ceramics, visit the Roman amphitheatre and see the Egubine tablets in the Palazzo dei Consoli. Afterwards relax and observe the locals with a refreshing drink in the magnificent Piazza Grande. (4hrs/12km)

Day 4

Monte Oliveto Maggiore & Siena street party dinner

A spectacular drive through the eroding landscape known as the crete senese takes us to the 14C Abbey of Monte Oliveto Maggiore. Here in its cloister some of the finest renaissance frescoes by Sodoma & Signorelli tell the life story of St Benedict. After lunch continue on to Siena to meet our local Sienese guide for a walking tour oriented specifically to the Palio horse race. Time now to stroll at leisure taking in the buzzing pre-race atmosphere and then join a participating Contrada (district) for a pre-Palio street party dinner – which the contrada horse also attends!

Day 5

A Tuscan Experience: Vino Nobile and The Race

Enjoy a leisurely morning before visiting the Avignonesi winery, which produces one of the finest Vino Nobile di Montepulciano. The guided tour of the winery is a fascinating insight into the making, ageing and bottling of wine and the ongoing experiments undertaken by the De Salvo family so as to remain at the forefront of high quality wine production. Lunch at the winery is a four course meal with four different wines carefully selected to enhance the tasting experience. What could be a more enjoyable way to prepare for Il Palio? So, let us take our seats around the Campo, watch the pageantry and enjoy the Race.

Day 6

Pienza – Montichiello – Montepulciano

Today we explore the renaissance town of Pienza enjoying the delicious smells of Pecorino cheese and admiring the Duomo and Palazzi in its idyllic piazza. Then walk along country lanes to the walled hamlet of Monticchiello and through the vineyards to Montepulciano, where an avenue of Tuscan cypresses lead us to the renaissance Tempio di San Biagio. We enter the town through a medieval gate and arrive in the main square via the 14C vaulted cellars of the Cantina del Redi, where you can taste the local Vino Nobile di Montepulciano. (4hrs/12km)

Day 7

Medieval Cortona

The spiritual and tranquil setting of Le Celle, a 12C Franciscan hermitage is the start of our walk and takes us to Cortona. Entering through one of the ancient city gates, we explore its myriad of medieval streets and monuments. Time to collect any last minute souvenirs or another gelato, but don’t spoil your appetite before a tasty picnic in the shady tree-lined park. We return to relax and pack before our farewell dinner party. (3hrs/8km)

Day 8

Depart from Terontola

Scheduled departure at 9.00 for Terontola-Cortona station (20mins). If you wish, can help you to extend your stay or make other independent departure arrangements.

Cortona: 7 nights

Some useful links for you to use while getting ready for your tour.

Other tour ideas:

Special interest tours – view all


Gourmet Cookery Classes and Wine Tasting in Tuscany

Our gourmet cooking classes take place at Molino di Bordone, among the Tuscan and Umbrian hills, only minutes from the beautiful Etruscan walled town of Cortona.


Amalfi Coast Walking & Hiking

Sensational coastal scenery of limestone cliffs, serpentine roads and terraced lemon groves with famous towns like Amalfi, Positano and Ravello. Villages and remote monasteries here have long been connected by a series of ancient footpaths perfect for walking and hiking.

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