Ride from Castle to Castle – A Luxury Horseback Experience in Tuscany

Discover the magic of Tuscany on an unforgettable horseback journey from 15th-century castles to picturesque hilltop villages. Ride through cypress-lined paths, ancient olive groves, and rolling hills, while immersing yourself in local history, culture, and cuisine. Learn about the prestigious Palio horse race from a former professional jockey, and indulge in authentic Tuscan dishes prepared by a castle chef.

What You Will Experience

• Ride between historic castles – From 15th-century Castello del Calcione to Castello di San Fabiano, ending in the charming village of Vescona.
• Authentic Tuscan cuisine – Enjoy traditional dishes prepared by the castle’s chef and savor the region’s finest products.
• Palio horse race tradition – Learn from a former professional Italian jockey about Siena’s most famous medieval festival.
• Breathtaking landscapes – Ride through vineyards, olive groves, cypress alleys, and historic villages.
• Immersive 4-day itinerary – Including castle stays, scenic rides, cultural visits, and local gastronomy.
• Optional activities – Truffle hunting, massages, canoe rides, e-bike tours, cooking classes, and more.

Itinerary

Day 1 – Arrival in Florence or Rome – Castello del Calcione

• Private transfer from Florence or Rome to the 15th-century Castello del Calcione, surrounded by forests, lakes, olive groves, and wildlife.
• Settle into your room and, depending on arrival time, meet the horses and find your perfect riding companion.
• Aperitivo and drinks followed by a welcome dinner in the castle’s main dining room.
• Overnight at Castello del Calcione.

Day 2 – Castello del Calcione to Castello di San Fabiano

• After a homemade breakfast, depart on horseback to Rapolano for a coffee break.
• Continue riding through the Senese rolling hills to lunch at the agriturismo “Il Poderino.”
• Ride on to Monteroni d’Arbia before reaching Siena, home of the prestigious Palio horse race. Explore the city and enjoy dinner near Piazza del Campo.
• Overnight at Castello di San Fabiano.

Day 3 – Castello di San Fabiano to Vescona

• Enjoy breakfast at the castle before riding along the Leonina Trail, historically used by Palio jockeys to train their horses.
• Stop for lunch at Castello di Leonina with panoramic countryside views.
• Afternoon canters through the Crete Senesi, riding along the famous race track to Vescona – home of Palio champion jockey Bastiano.
• Aperitivo and dinner “on the top of the world.”
• Overnight at Bastiano’s House.

Day 4 – Return to Castello del Calcione – Departure

• Breakfast and a final morning ride through Mucigliani, Torre a Castello, oak forests, and olive groves.
• Picnic lunch in a scenic spot before returning to Castello del Calcione.
• Private transfer back to Florence or Rome.
• Optional: Additional night at Castello del Calcione or in Florence.

What’s Included

• Guided horseback rides between castles and villages
• 3 nights in historic Tuscan castles
• All breakfasts, lunches, and dinners as per itinerary
• Guided visit and insights into the Palio tradition
• Professional local guides
• Transfers from/to Florence or Rome

What’s Not Included

• Optional activities (available upon request)
• Tips (optional)
• Additional nights at the castle or in Florence

Pricing

Please contact us for a customized price based on your group size, preferred dates, and activity choices.

Bookings

Contact us via WhatsApp with your desired travel dates – we’ll arrange your dream horseback riding holiday in Tuscany.