Palio di Siena
Siena, Italy
The Palio di Siena
Inaugurated in 1633 and raced twice a year ever since.
Imagine a thrilling horse race in the heart of Siena, where 10 bareback riders and their horses charge through the Piazza del Campo in a fierce competition where anything goes…
Come and experience this extraordinary event through the eyes of your incredible host. Over the course of a few days, you’ll immerse yourself in the excitement, gaining exclusive behind-the-scenes access that only she can provide.
Nestled in the heart of Tuscany, you'll stay at the breathtaking Calcione Estate run by the same family since its construction in 1483.. This magnificent retreat offers the perfect base for this incredible and unforgettable experience.
Whether it’s just the two of you or a private group of 30, the entire estate can be exclusively yours and the experience tailored made to you.
Meet the Host: Selvaggia
Passionate about horses and making history as the only woman training to compete in the prestigious Palio di Siena, Selvaggia leads the Scuderia at Calcione, where she breeds and trains her own racehorses for this legendary event.
Now, she invites you to join her on her unforgettable adventure—offering a rare, insider’s perspective on the Palio.
Having lived this experience multiple times, we can say with confidence—this is a bucket list event you won’t want to miss!
The Experience
The Palio Experience : 3 Nights
The Full Palio Immersion: 4 Nights
Stay in an incredible Estate in the heart of Tuscany
Whether it’s just the two of you or a private group of 20, the castle can be exclusively yours and the experience tailored made to your group.
Cost for 3 days: £1,050 per person based on shared accomodation.
Dates:
1st to the 4th of July
14th to 17th August
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Two Options:
The Palio Experience (Day 1, 3, 4 & 5)
The Full Immersion (Day 1, 2, 3, 4 & 5)
Day 1: Arrivals and Dinner
Welcome to the Calcione Estate! After settling into your charming house adjacent to the castle, refresh yourself with a dip in the freshwater lakes or relax for an afternoon of Far Niente by the pool… As night falls, get ready for aperitivo and unwind with a delightful dinner at the castle.
For The Palio Experience (3 days), guests will arrive on the day of the Contrada dinner.
Day 2: The Tratta and The Assegnazione (extra day for the “Full Immersion”)
Early wake up call for a full day immersion of the Pre Palio guided by Selvaggia. You will witness two main events:
The Tratta (9 AM) : The thrilling selection process of the 10 horses that will race on the Piazza.
The Assegnazione (Midday) : Witness the assignment of the horses to each Contrada, arguably the most emotional moment of the Palio.. Follow a Contrada as they escort their horse to their neighborhood stable, immersing yourself in the excitement and tradition up close.
Coming back to the Calcione, embark on an evening ride through the estate, weaving through ancient olive groves at sunset..
For dinner, a table will be reserved for you at a charming local restaurant where you will be get a taste for all the incredible “Primi” and Secondi” as well as the most delicious red wines (10 minutes drive away).
Day 3: Contrada Dinner
The night before the Palio is one of the most exhilarating celebrations leading up to the legendary race.
With 25,000 Sienese gathering, the streets glow with torches and lanterns as massive communal tables fill the main squares, each belonging to a Contrada. Thanks to her connections, you’ll have a coveted seat among the locals, sharing in the excitement!
The atmosphere is electric—flags wave, voices chant, and anticipation fills the air. As Siena prepares for the epic race, you’ll experience the true spirit of the Palio firsthand..
Day 4: Race Day
Head to Siena in the morning to witness the horses being christened in church before the race, and soak in the city’s vibrant energy as the streets come alive. After a local lunch, watch all 17 Contrade parade through the city, proudly waving their flags and beating their drums, dressed just as they were in the Middle Ages.
By 4 PM, make your way to a private apartment, where a window has been specially reserved for you to enjoy the spectacle in comfort and with the best view imaginable!
With an aperitivo in hand, you’ll meet Trecciolino, the legendary 13-time Palio winner, who will share insider knowledge on the race’s history, strategies, and secrets—just before you witness the breathtaking event together!
After the race, head to the streets to feel the electricity of the winners parading their winning Jockey and horse until the early hours and have dinner in town sharing all the incredible excitment!
Day 5: Farewells and departures
After breakfast, relax a last time by the pool or take a dip in the lake before heading back to the aiport..
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For the full immersion, horse riding can be swapped with any of the below:
Horse riding
Bike trails
Wine tasting
Olive Oil tasting
Truffle Hunting
Canoeing
Available anytime at the Estate:
Wild swimming in the Lakes
Hikes
Tennis
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The Calcione Estate is located in the heart of Tuscany, 40mn car ride from Siena.
How to get there:
Flight to Florence. Car ride from the airport to the Estate about 1h20mn.
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Accomodation: £1,100 per room Includes:
Accomodation for 3 nights (10 double bedrooms available, average price as some nicer than others)
Daily breakfast
VAT & Service charges
The Palio Experience: £ 500 per person * Includes:
Thursday Dinner and Friday lunch at the castle (including wine).
A private window with aperitivo to watch the race the day of La Prova from an apartment with Trecciolino, the legendary 13-time Palio winner guiding you through the race.
*Number/ cost of windows varies depending on number of guests.
The pre race dinner with the Contrada (including wine).
VAT & Service charges
The Full Palio Immersion - 4 Nights:
Accomodation: £1,400 per room for 4 nights including breakfast
Palio Experience: £1,300 per person: Includes in addition to the above, an extra day for The Tratta and The Assegnazione with Selvaggia as a guide, Horseback riding at the Estate and an additional dinner at the estate.
* The window costing about £1,000 per person on race day, we have some cheaper alternative such as:
Window on Prova day (the day before) - included above.
Places on the square on race day (around £500) or prova day ( a little cheaper).
Standing on the square (free and a must do!)
Not Included:
Flights
Lunch on the saturday (on the go in town)
Dinner on the saturday (you might want to stay in Siena or go to the After Race Party if happening - we can also organize an additional dinner at the estate)
Transfer (recommended to rent a car, transfers can be organized daily to and from Siena and to and from the aiportt).
The Palio Race Explained
Origins:
In the mediaval times, the town's central piazza was the site of public games, such as bullfights. Horse races organized by the contrade were run across the whole city and called palio alla lunga.
When the Grand Duke of Tuscany outlawed bullfighting in 1590, the contrade started to organize races in the Piazza del Campo with the first ones on buffalo-back and then on donkey-back. The first modern Palio on horse-back (called palio alla tonda) took place in 1633.
What is the Palio:
The Palio di Siena is the culmination of ongoing rivalry and competition between the contrade through a bareback horse race that takes place in Siena's main square, Piazza del Campo .
When does it happens:
The Palio takes place twice a year, on July 2nd (Palio di Provenzano, in honor of the Madonna of Provenzano) and August 16th (Palio in honor of the Madonna dell'Assunta).
The Prize:
The winning contrada receives a silk banner (the Palio), which is a symbol of victory and pride.
The Contrade:
The event is deeply rooted in the identity of Siena's 17 districts (contrade), with each contrada having its own history, traditions, and fierce rivalries.
The Jockeys:
Jockeys, known as "ragatii," ride bareback, and the race is known for its intense competition and the possibility of a horse winning even without a jockey.
The Race:
Ten contrade participate in each race, with the horses chosen randomly by lottery. The race is run for three laps of the piazza, lasting only a few minutes.
Few things are forbidden to the jockeys during the race; for instance, they can pull or shove their fellows, hit the horses and each other, or try to hamper other horses at the start…
ACCOMMODATION
You will stay at Selvaggia’s family estate:
Il Castello del Calcione.
Surrounded by ancient woodlands, serene lakes, abundant wildlife, charming farmhouses & flourishing olive groves. This picturesque sanctuary lies in the heart of Tuscany, offering a tranquil escape off the beaten path.
Play some tennis, enjoy La “ Farniente” by the swimming pool or admire the stunning race horses, breed and trained by Selvaggia on the estate.
Whether it’s just the two of you or a private group of 20,
the castle can be exclusively yours and the experience tailored made to your group.
THE ITINERARY
The Palio Experience (Day 1, 3, 4 & 5)
The Full Immersion (Day 1, 2, 3, 4 & 5)
Day 1: Arrivals and Dinner
Welcome to the Calcione Estate!
After settling into your charming house adjacent to the castle, refresh yourself with a dip in the freshwater lakes or relax for an afternoon of Far Niente by the pool…
As night falls, get ready for aperitivo and unwind with a delightful dinner at the castle.
For The Palio Experience (3 days), guests will arrive on the day of the Contrada dinner.
Day 2: The Tratta and The Assegnazione
(extra day for the “Full Immersion”)
Early wake up call for a full day immersion of the Pre Palio guided by Selvaggia. You will witness two main events:
The Tratta (9 AM) : The thrilling selection process of the 10 horses that will race on the Piazza.
The Assegnazione (Midday) : Witness the assignment of the horses to each Contrada, arguably the most emotional moment of the Palio.. Follow a Contrada as they escort their horse to their neighborhood stable, immersing yourself in the excitement and tradition up close.
Coming back to the Calcione, embark on an evening ride through the estate, weaving through ancient olive groves at sunset..
For dinner, stay at the castle for another dinner under the star or venture to the charming local restaurant where you will be get a taste for all the incredible “Primi” and Secondi” as well as the most delicious red wines (10 minutes drive away).
Day 3: Prova & Contrada Dinner
The day before the Palio is one of the most exhilarating celebrations leading up to the legendary race and only trial for the jockeys and their horses.
With 25,000 Sienese gathering, the streets glow with torches and lanterns as massive communal tables fill the main squares, each belonging to a Contrada. Thanks to her connections, you’ll have a coveted seat among the locals, sharing in the excitement!
The atmosphere is electric—flags wave, voices chant, and anticipation fills the air. As Siena prepares for the epic race, you’ll experience the true spirit of the Palio firsthand..
Day 4: RACE DAY
Get ready for the most thrilling race of your life!
Head to Siena in the morning and maybe try to witness the horses being christened in church before the race, and soak in the city’s vibrant energy as the streets come alive. After a local lunch, watch all 17 Contrade parade through the city, proudly waving their flags and beating their drums, dressed just as they were in the Middle Ages.
By 4 PM, make your way to a private apartment, where a window has been specially reserved for you to enjoy the spectacle in comfort and with the best view imaginable!
With an aperitivo in hand, you’ll meet Trecciolino, the legendary 13-time Palio winner, who will share insider knowledge on the race’s history, strategies, and secrets—just before you witness the breathtaking event together!
After the race, head to the streets to feel the electricity of the winners parading their winning Jockey and horse until the early hours and have dinner in town sharing all the incredible excitment!
Day 5: Farewells and Departures
After breakfast, relax a last time by the pool or take a dip in the lake before heading back to the aiport..
