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
☼ 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
☼ 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
Truffle Hunting
Truffle hunting is a one-of-a-kind harmonious break offering nature, gastronomy, relaxation, and culture.
Castello del Calcione is home to one of the region’s most important Tartufaia.
This precise area in the woods is particularly fertile and adapted to the natural growth of tuber melanosporum, which is one of the finest types of black truffles. Your search for black gold will be led by a hunter and his dog.
E-Bike Tour
Ever dreamt of conquering the Tuscan hills by bicycle? Indulge in this new way to discover the region and its secrets.
Our knowledge of the territory and paths guarantees guests an unforgettable experience.
Through our guided or self-directed tours, you can discover Valdichiana or Valdorcia while enjoying savory local products – from wine to cheese
Siena Visit/Lunch
Step into a living masterpiece of medieval architecture and history with our exclusive Siena tour.
Nestled in the heart of Tuscany, Siena is a breathtaking city that transports you back to the 13th century, preserving its original Gothic character with remarkable authenticity.
Experience the magic of a city that has maintained its authentic charm for over 800 years.
Cooking Classes w/Chef
Cooking Classes w/Chef
Join our expert chef in an authentic culinary journey.
Learn the art of traditional Italian cooking as you prepare a delightful dinner from scratch, using fresh local ingredients and time-honored techniques.
This hands-on cooking class offers an intimate glimpse into genuine Tuscan gastronomy, where every recipe tells a story of family, tradition, and passion.
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
The Castles of Tuscany Tour is tailored to accommodate intermediate to experienced riders who are confident riding at all three gaits - walk, trot, and canter - especially in open countryside.
You will spend between 3 and 6 hours per day in the saddle, covering distances of 15 to 25 km daily to reach each castle. For this reason, good physical fitness and stamina are essential.
During the tour, you will be riding athletic horses such as Thoroughbreds, Anglo-Arabs, and Sella Italiana. While our horses are exceptionally well-trained, gentle, and responsive, these breeds are energetic and enjoy moving freely over varied terrain. Given their spirited nature, it is important that you feel confident and comfortable riding at faster paces, especially cantering in open countryside.
If you are looking for a more relaxed, stationary experience, we recommend our Calcione Experience, in Italy, our Irish Castle Escape, in Ireland, or our Lusitanos & Dressage in Provence, in France - all of which are tailored for intermediate to experienced riders but feature shorter riding days and more opportunities for relaxation.
If you find yourself uncertain about your suitability for this ride, we are here to help and assist you. Please feel free to contact us via our Contact form, email, or WhatsApp, and we will be more than happy to guide you.
Yes. Our commitment lies in curating tailor-made experiences that cater to the unique preferences and needs of each of our guests. This includes accommodating dietary restrictions and allergies to ensure a seamless and enjoyable journey.
Prior to embarking on a horse riding holiday or day trip, we request guests to complete a comprehensive form. This form allows us to gather essential information, not only about dietary restrictions and allergies but also about your gastronomic preferences. By doing so, we can craft an experience that not only meets but exceeds your expectations.
Your safety, well-being and satisfaction are at the forefront of our personalized service, making every ride with us a truly unforgettable experience.
As a general guideline, the minimum age for participants is 6 years old. However, age restrictions can vary based on the destination and individual circumstances. We take into consideration factors such as size, stamina, and riding ability, as well as the dynamics of the group.
If you find yourself unsure whether a horse-riding holiday is the perfect fit for your family, particularly when considering the participation of your children, do not hesitate to reach out to us. We understand that safety and comfort are paramount, especially when it comes to younger riders. We will be more than happy to assist you in making an informed decision. Please feel free to contact us via our Contact form, email, or WhatsApp.
When gearing up for your horse-riding adventure, packing the right essentials is crucial for a comfortable and enjoyable experience. Each horse-riding holiday is unique, and your packing list will be influenced by factors such as the weather conditions, the ride’s difficulty, the destination’s disease risks and sometimes dress code requirements for riding in nature. Before embarking on your journey, we provide guests with a comprehensive list tailored to their specific horse-riding holiday.
We have outlined a typical packing list designed to cover the basics for riders :
For the time in the saddle:
- Riding Pants: Choose the fabric based on the weather of the destination, ensuring comfort and adaptability.
- Riding Boots and Chaps: If not provided on-site, these are essential for a secure and comfortable ride.
- Lightweight Riding Helmet: Ensure you have a suitable helmet for protection, especially if not provided on-site.
- Sports Bras for Women: Prioritize support and comfort during rides.
- Long Socks: Opt for woolen ones in colder weather to keep your feet warm and cozy.
- Button-Up Long-Sleeved Cotton Shirts: Choose thermal options in cold weather for added warmth.
- Fleece or Wool Jumper: Layering is key, and a jumper provides insulation during cooler rides.
- Waterproof Windbreaker Jacket: Be prepared for unexpected weather changes with a reliable, waterproof jacket.
- Waterproof Over Trousers: Protect yourself from rain and wind with these essential over trousers.
- Sunglasses: Shield your eyes from sun, wind, and dust for a clear and comfortable ride.
- Riding Gloves: Ensure a good grip and protect your hands during the ride.
- Filtered Water Bottle: Stay hydrated with clean water throughout your journey.
- Sunscreen: Guard against sun exposure, especially for extended rides under the open sky.
For after the ride:
- Hat and Gloves : Stay warm during chilly evenings after your ride.
- Sun Hat: Shield yourself from the sun during the afternoon visits.
- Soft Shoes: Slip into comfortable footwear after hours in riding boots.
- Comfortable Loungewear: Relax and unwind post-ride with comfortable clothing.
- First-Aid Necessities: Be prepared with a basic first-aid kit, based on your medical needs.
- Paracetamol: For general pain relief and fever.
- Gastro-Stop Medication: To address digestive issues if they arise.
- Nurofen or Ibuprofen: In case of muscle soreness for a comfortable recovery.
Lip Balm: Keep your lips moisturized, especially in varying weather conditions.
On The Castles of Tuscany Tour, you will be welcomed and led by 2 local passionate horse-riding guides, who are fluent in English, & Italian.
For the Castles of Tuscany Tour, our partnering tour operator does not require participants to have travel insurance and medical coverage. However, we highly recommend securing travel insurance and medical coverage for your convenience and peace of mind.
Should you decide to purchase insurance, please ensure that it covers personal liability, medical expenses (including emergency medical evacuation and repatriation), accidental injury, and holiday cancellation. The coverage must be valid from the moment your booking is confirmed until the end of your trip.
While travel and medical insurance are not included in our standard packages, we are happy to arrange it for you at an additional fee of 5% of the total journey cost.
We recognize the importance of being prepared for the unexpected, and, upon request, we will provide a comprehensive insurance package to ensure you can travel with confidence.
If you have any questions about the insurance options available, please don’t hesitate to reach out via our Contact form, email, or WhatsApp. Your safety and peace of mind are our highest priorities.
To confirm a ride’s booking with us, guests have the possibility of sending a deposit through two payment options: Traditional bank transfer or Secure payment link.
Traditional bank transfer provides a secure and direct way to process payments.
Alternatively, secure payment link offers more convenience but usually includes additional card payment fees.
For The Castles of Tuscany Tour, we accept riders weighing up to 90 kg (198lbs).
This limit ensures the safety and well-being of our horses, as they cannot comfortably carry more weight.
A GLIMPSE INTO THE CASTLES OF TUSCANY TOUR
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