Castles of Tuscany Tour
- Ride from 15th Century Castello del Calcione to Castello di San Fabiano, up to the charming town of Vescona
- Savor the best of Tuscan cuisine crafted by the Castello's Chef
- Learn about the famous Palio Horse Race discipline from a former professional Italian jockey
Optional : Additional night at the Castello, Truffle hunting, Massages, Canoë ride, E-Bike Tour, Cooking Class, etc...
Centrally located in Tuscany, Calcione is easily accessible from Rome or Florence.
On your departure day, our driver will collect you from the airport/your hotel in Rome/Florence and transport you to your accommodation for the first night.
The journey to Calcione typically takes 45mins from Siena, 1h30 from Florence, and 2h from Rome.
For our set departures, the Castles of Tuscany Tour is tailored to accommodate intermediate to experienced riders; comfortable riding at all 3 paces and cantering in open nature.
You will spend between 3 to 6 hours in the saddle each day in a group of 4 to 6 riders, with thoroughbred, Anglo Arab, Sella Italiana, who love to gallop (just like us!).
If you are seeking for a private and custom experience, we are happy to craft a flexible schedule tailored to your preferred riding time and desired activities.
Contact us to design your ideal Tuscan riding escape.
In addition to our set departures, we also offer private rides to Tuscany, allowing you to tailor your experience. You can customize various aspects of your journey, including the number of riding days, time spent in the saddle and accommodations along with other activities.
Tell us about it, and we will turn it into a reality : Contact us for a Tailor-Made journey.
When you reach out through our booking or contact form, our team will provide you with a comprehensive brochure of your chosen journey. This booklet includes the full itinerary, details about accommodations, rates, and available departure dates (along with many pictures to give you a glimpse of the ride!).
If the journey aligns with your wishes and you would like to join, we will send you a detailed form to complete. This helps us understand your riding level, background, and experience, ensuring you meet the required skill level for the ride. This step not only prioritizes safety but also guarantees an enjoyable experience for the entire riding group.
Once our team and riding guide confirm your suitability, you can secure your saddle by paying a 50% deposit.
For your convenience, this can be easily completed via our secure payment link or through a traditional bank transfer.
Just a short journey from the cradle of the Renaissance, Florence, lie hidden gems awaiting discovery: the 15th Century Castles of Tuscany.
This region, celebrated for its picturesque landscapes of rolling hills and verdant vineyards, rich millennia-old history, and culinary delights, stands as a major historic, cultural, and artistic center. From the pre-Roman era to the Medici and other influential Italian families, Tuscany’s long history is filled with fascinating chapters for you to discover.
Set out for an immersive luxury horse ride within this charming corner of Tuscany, where you will be warmly welcomed in 15th Century family-owned castles, discovering the prestigious Palio race, an event steeped in pride and tradition, and indulging in the finest Italian cuisine.
Under the cypress alleys, through ancient villages, and past olive groves, prepare for an off-the-beaten-path horse-riding holiday where serenity and authenticity come hand in hand. A magical experience within Tuscany’s one-of-a-kind natural, cultural, and historical heritage.
The schedule
FROM FLORENCE TO CALCIONE
☼ A.M – Upon arriving from your flight to Florence or Rome, our driver will take you to Castello del Calcione, an ancient family-owned estate, surrounded by untouched woods, lakes, wildlife, farmhouses, olive groves, and of course, horses.
☽ P.M – After settling in your room and visiting the castle – depending on your time of arrival – you will have the possibility to try out the horses and find your perfect companion for the adventure. Aperitivo and drinks will be followed by dinner in the castle’s main dining room.
☽ Night at Castello del Calcione
FROM CALCIONE TO SAN FABIANO
☼ A.M – After savoring a delicious homemade breakfast, begin your ride from the castle at 9:30 to set for the charming town of Rapolano. After a short coffee break, we will ride through the Senese rolling hills, and stop for lunch at the agriturismo “Il Poderino”.
☽ P.M – The ride will continue all the way to Monteroni d’Arbia before reaching the town of Siena – the prestigious town of Palio. Stroll through its charming streets, before having dinner next to Piazza del Campo, allowing us to delve deeper the Palio topic – a medieval festival annually in Siena featuring bareback horse races.
☽ Night at Castello di San Fabiano
San FABIANO TO VESCONA
☼ A.M – This morning, you will have plenty of time to savor breakfast in the enchanting grounds of the Castello di San Fabiano. Late morning, we will set for the Leonina Trail, which is the famous historical route used by the Palio jockeys to train their horses.We will stop for lunch at Castello di Leonina enjoying a beautiful view over the Tuscan countryside.
☽ P.M – In the afternoon, set for beautiful canters through the Crete and on the most famous race track that leads up to Vescona, which is the house of Bastiano, a famous jockey who won multiple times the Palio. Aperitivo and dinner will be served on “the top of the world”!
☽ Night at Bastiano’s House
Departure to Florence/Rome
☼ A.M – Upon savoring breakfast and enjoying for a last time this wonderful view, begin the ride at 10 a.m to explore another type of landscape. We will cross two small towns, Mucigliani and Torre a Castello, as well as oak forests and olive groves. We will stop again for a picnic in a carefully selected spot before riding back to Calcione.
☽ P.M – In the afternoon, back at Castello del Calcione, our driver will take you back to Florence/Rome to catch your flight.
☽ Option : Additional night at Calcione or Florence.
What our riders say
Optional activities
Accommodations
Your accommodations in these Tuscan Castles are more than just comfortable and tastefully-designed rooms; they are an immersion into the heart of Italian history, a journey back to the regal elegance of bygone eras.
These 15th Century, family-owned castles are nestled in the heart of Tuscany’s countryside, offering incomparable views on the region’s picturesque landscapes. With their ancient stables, expansive manicured gardens, and tranquil pool areas, the properties promise a peaceful and authentic escape.
Each room harmoniously blends traditional aesthetics with contemporary comfort, providing a subtle nod to the past while ensuring a stay filled with coziness.
Here, tradition and comfort intertwine, creating an environment where guests can experience the tranquility, authenticity, and timeless charm of rural Tuscany.
CASTELLO DI SAN FABIANO
"A family-run charming Castle" - Intimacy, Elegance & History
BASTIANO'S B&B
Unrivaled view over Vescona's rolling hills - Warmth, Simplicity & Authenticity
CASTELLO DEL CALCIONE
"A haven of wilderness and peace" - Warmth, Elegance and History
About this ride
Frequently asked questions
A GLIMPSE INTO THE CASTLES OF TUSCANY TOUR
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