Tuscany, Italy

The Castles of Tuscany – Italy

Ride from castle to castle & Immerse into Tuscan culture

Ride overview
  • 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
  • Discover the famous Palio horse race discipline from professional Italian jockeys
  • Optional : Truffle hunting, Massages, Canoë ride, E-Bike Tour


4 Days & 3 Nights

  • 11th to 14th APRIL – 6 saddles available
  • 9th to 12th of MAY – 3 saddles available
  • 23rd to 26th of MAY – 4 saddles available
  • 6th to 9th of JUNE – 6 saddles available
  • 20th to 23rd of JUNE – 6 saddles available


Tailor-made journeys are available for private groups (>2 people) from March to June and from September to November. Our partnerships with luxury estates and châteaux, along with trusted touring partners, grant us exclusive access to first-class accomodations and activities to craft the journey of your dreams. Tell us about it, and we will turn it into a reality : Inquire for a Tailor-Made Journey.


Our driver and guide will be picking you up at the airport/your hotel, and take you to the heart of the Tuscany, where your accommodation awaits you. The driving time is approximately 1h30 from Florence and 2h from Rome.


For Fixed Group Departures, the Castles of Tuscany on Horseback are tailored to accommodate intermediate to experienced riders. The Tailor-Made journeys are crafted to accommodate beginners to experienced riders upon inquiry.


On the Fixed Group Departures, you will be spend between 3 to 6 hours in the saddle each day. On the Tailor-Made Journeys, you can choose the time you spend in the saddle, visiting the areas, etc.

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 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.


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.

The schedule - sample itinerary


☼ 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


☼ 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


☼ 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


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* If you are alone and wish to join a group ride, please mention "Solo Rider"
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You can let us know about any inquiry you have on Nomad Riders or the rides we propose. If you selected the Tailor-Made Journey, kindly indicate your desired destination and any specific preferences or requirements you may have for us to craft the perfect ride for you.