The Palio di Siena

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The focal point of this small group tour – which we offer only in the first week of July – is the unique experience of attending the incredible and exciting horse race called the Palio di Siena. Along with the trip to Siena for the race, we have made a delightful selection of excursions in Tuscany and Umbria to medieval hill towns like Pienza and Gubbio, a visit to Monte Oliveto Maggiore abbey and of course time to spend in medieval Cortona. Good food an wine and fun compliments the itinerary as we build up the tension and excitement for this oldest and most famous horse race in the world…

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  • Vacation Style Holiday Type
    Food & Wine, Walking & Hiking
  • Activity Level Fairly Easy
  • Group Size Small Group
All about the The Palio di Siena.


Held twice a year on 2nd July and 16th August in the historical Piazza del Campo square in Siena in honour of the Virgin Mary, Lady and Patroness of the City is the Palio di Siena. The focal point of our small group tour is the unique experience of attending this crazy and exciting, 90 second bareback horse race.

It has been held almost uninterrupted for 500 years, since the days of the medieval Republic of Siena. Preceded by a colourful procession of historic pageantry with traditional costumes, drummers and flag throwers, experiencing the Palio is like watching ritualised warfare, in which the jockeys are the mercenaries!

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. The 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!

As part of the build-up we pick a Contrada to support,  attend the celebration dinner the night before and watch the trial races. Then it is time for the race and we take our seats in the stalls.

Enjoy this wonderful summer trip to central Italy which you can combine with your travels to other parts of Europe.

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.

Your wallet? You won’t need it! Except for postcards and souvenirs we’ll take care of everything

  • 2 experienced guides 24/7
  • All breakfasts, lunches and dinners as per itinerary
  • Wine, water & coffee with meals
  • All accommodations
  • Walking sticks
  • All gratuities for baggage, porters and hotel service
  • Minibus transport from start to finish
  • Entrance fees to museums, events and parks as listed on itinerary
  • Local specialist guiding fees
Whats not included in this tour.Items that are not included in the cost of tour price.
  • Flights
  • Transfer to the meeting point
  • Travel insurance and other emergencies
  • Visa fees and entry clearing fees
  • Single room accommodations
  • 1 lunch & 1 dinner
  • Minibar
  1. Day 1 Terontola-Cortona

    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.

  2. 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)

  3. Day 3 Gubbio

    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)

  4. 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!

  5. 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.

  6. 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)

  7. 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)

  8. 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.

Live a unique experience during this timeless and charming horse racing

Discover the beauty of Tuscany

Accommodation Standard

Accommodations are an important point of your overall holiday experience. One of our first thought is to find and choose the best hotel and b&b solutions, ensuring that each night of your itinerary finds you comfortably settled in a space that is welcoming and full of authentic local charm.

When considering a hotel, we look at more than just the rooms and wherever possible, we arrange for stays close to the places you most dream of seeing like historically iconic, coveted high-design or supremely located at the edge of a wilderness.

Take a closer look at some of the properties we have chosen for your next Caspin Journeys holiday!

Siena il PalioYour dream accommodation you will find on this tour
Molino di Bordone
Cooking Class Kitchen
One of the accommodations

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