Palio di Siena
2nd July 2026 | 16th August 2026
Experience the Palio di Siena: A Timeless Tradition of Passion, Pageantry, and Pure Adrenaline
We create bespoke travel packages that immerse you in every unforgettable moment — from exclusive vantage points and official hospitality to personalised itineraries and behind-the-scenes experiences.
Spaces on our experiences are limited and sell out every year, so get in touch and start creating your perfect trip today.
Frankie Dettori
RacingBreaks.com Founder & Ambassador
The Palio di Siena is an electrifying fusion of medieval tradition, fierce local rivalry, and breathtaking spectacle — where the thunder of hooves racing through Siena’s historic Piazza del Campo is matched only by the vibrant colours, centuries-old pageantry, and the palpable pride of each Contrada. This is not just a horse race; it’s a cultural phenomenon that captures the heart of a city and leaves a lasting impression on all who witness it.
Our Palio di Siena Experiences
Whether you’re looking to experience the thrill of the race from an exclusive grandstand seat, soak in the electric atmosphere from a private balcony, or fully immerse yourself in the traditions with access to Contrada celebrations and pre-race dinners, our expertly crafted packages offer something for every traveller.
Luxury Experience | Castel Monastero Resort ✰✰✰✰✰
from £3,195 per person
Trip Dates:
July Palio | 30th June - 3rd July 2026
August Palio | 14th August - 17th August 2026
Limited Spaces
Book with just a 10% deposit!
Castel Monastero offers a unique opportunity to experience the Palio di Siena while enjoying the serenity and sophistication of one of Tuscany’s finest countryside retreats. Set within a beautifully restored medieval village, it is the perfect choice for those seeking a blend of five-star luxury, peaceful surroundings, and effortless access to the excitement of race day.
What's Included?
- Private return airport transfers
- Three (or more) nights accommodation
- Breakfast each morning
- Tasting Menu Dinner in the Contrada Restaurant at Castel Monastero
- Wine tasting at Castel Monastero with the hotel's sommelier
- Dinner in one of the “Contrada” the night before the Palio
- Access to the “acqua benessere” indoor Spa.
- Access to an exclusive terrace in a historical palace overlooking the Piazza del Campo
- A light Tuscan buffet and open bar during the race
Palio di Siena Example Itinerary
Below is an example itinerary based on our three night experience based at the Castel Monastero Resort attending either the July or August Palio. Trip extensions are available should you wish to extend your time in Siena or visit another city such as Rome, Florence or Pisa.
Day 1: Tuesday 30th June 2026 | Friday 14th August 2026
- Upon arrival into either Florence or Pisa you will be collected by private vehicle and transferred directly to Castel Monastero.
- Upon arrival at the hotel you will have the remainder of the afternoon at leisure
- That evening you will enjoy dinner in the hotel's restaurant, La Contrada.
Day 2: Wednesday 1st July 2026 | Saturday 15th August 2026
- Enjoy breakfast at the hotel and then you'll have time to relax and can take advantage of access to the hotel's spa.
- That afternoon you'll enjoy Wine Tasting with the hotel's Sommelier.
- Later in the evening you will be transferred into Siena to experience a "Contrada Dinner". In previous year's we have been hosted by the Eagle Contrada and have dined at the feet of the Cathedral of Siena.
Day 3: Thursday 2nd July 2026 | Sunday 16th August 2026
- Enjoy breakfast at the hotel and you'll then have the rest of the morning at leisure.
- Later in the afternoon you will be transferred to Siena to take your place on an exclusive terrace from which you will view the Palio di Siena. You'll enjoy food & drink throughout the afternoon and evening as anticipation grows for the big race!
- Following the conclusion of the Palio you will be transferred back to the hotel.
Day 4: Friday 3rd July 2026 | Monday 17th August 2026
- Enjoy breakfast at the hotel .
- You will have your final day at leisure before being collected by private vehicle and transferred back to the airport to catch your flight home.
- Don't want your trip to end? Why not consider spending some time in Rome, Pisa or Florence before heading home?
About the Palio di Siena
This is a bi-annual race which takes place in the charming Piazza Del Campo; the centre square of Siena. The Palio is steeped with history and dates back to medieval times. A thrilling spectacle as jockeys race round the square bareback, using force to push past any opponent who stands in the way.
Packages include an insight into the culture and traditions of this Tuscan town and the race which brings each of the small contrades (city subdivisions) to battle for the ultimate title. Experience a banquet of Tuscan delicacies and listen to stories and tales of times gone by.
Enjoy the luxuries of the Castel Monastero hotel hidden amongst the rolling hills and vineyards of the Tuscan countryside. Relax and enjoy the spa, pool, restaurants, and elegant rooms at this stunning location and prepare for the energetic jamboree that is the Palio di Siena.
Flights to Italy
If required, our experiences can include flights to either Florence, Pisa or Rome.
Depending on your choice of departure airport you will fly to one of these cities before having the option to include airport transfers to your hotel.
Onward flights are possible for those looking to spend a few nights in another European city either before or after your time in Siena.
Flight upgrades are available to Premium Economy, Business & First Class subject to being an option on the flight booked.
Extend your trip
Why not use the opportunity of heading to Italy to visit some more of its stunning cities? Many of our guests spend a few nights in Rome, Pisa or Florence either at the beginning or end of their trips to make their most of their time away. But you could also travel further, with onward flights to other European cities also possible.
Reviews
"If you're thinking of going to see the Palio, please book it with Racing Breaks. The trip was well organised and professional. All going to plan. The hotel RB use is 1st class and would recommend The Castel Monastero as the rooms, restaurants, spa and staff would be difficult to improve. If you book RB give you the flexibility to extend the trip before or after so you can link it with seeing other parts of Italy. They are flexible with airport transfers too. Great bucket List experience thank you"