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.
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
Dates:
Full Immersion: 29th June to the 4th of July
Palio Experience: 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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Cost per person sharing a double bedroom:
The Palio Experience - 3 Nights : £3,200
The Full Palio Immersion - 4 Nights: £4,200
Included:
Accommodation with breakfast at Villa Giuseppe.
A private window to watch the race from an apartment with Trecciolino, the legendary 13-time Palio winner guiding you through the race.
The pre race dinner with the Contrada.
Plus for the Full Immersion:
The Tratta and The Assegnazione with Selvaggia as a guide.
Horseback riding at the Estate.
Not Included:
Flights
Lunches and other dinners.
Transfer (recommended to rent a car).
The horse riding van be replaced by
Massages (1 hr)
E-bike tours
Truffle hunting and wine paring
Cooking classes
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
Nestled in the heart of the estate, you'll stay in the newly refurbished and ever-charming Villa San Giuseppe.
With just five bedrooms and your own private swimming pool, you can enjoy a tranquil retreat where breakfast is served each morning, with only the soothing sound of crickets in the background.
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, 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
Get ready for the most thrilling race of your life!
Head to Siena in the morning and 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..
