Ride Overview
Ride and explore the villages and culture of the Castillian countryside, the largest area of Spain. Ideal for those looking for an active and fun ride.
Made prominent by the wool trade and the New World, this area can claim many great artistic and architectural treasures that are still prominent today. Set in the countryside outside of Segovia, whose aqueduct is the largest Roman structure in Spain, Segovia is host to Alcazar, the country’s most photographed castle – it resembles a fairy tale castle.
2025 Dates: March 9-16, April 6-13, June 8-15, Aug. 31-Sept. 7, Oct. 19-26
2025 Rates: $4,030.00 USD (or 3,200€) per person in a shared room (Single Supplement: $375.00 USD or 300€)
Non rider rate: 70% of rider rate
**Special itinerary which combines days from the Gredos Ride with days from this itinerary offered as follows:
Dates: June 1-8, June 15-22, Sept. 14-21, Sept. 28-Oct. 5
Rate: $4,160.00 USD (or 3,300€) per person in a shared room (Single Supplement: $375.00 USD or 300€)
NOTE: 4 riders minimum to confirm a departure. If less a $440.00 USD or 350€ fee will apply (per person) to run the ride. Fees will also apply for airport transfers.
Can’t break away for a week – try one of our short break options:
2025 Dates: March 19-23, April 2-6, April 16-20, May 7-11, May 28-June 1, July 2-6, Aug. 27-31, Sept. 10-14, Oct. 8-12, Oct. 15-19, Oct. 29-Nov. 2, Nov. 5-19
Rates: $1995.00 USD (or 1,550€) per person in a shared room. Single Supplement: $190.00 USD or 150€ (if less than 4 riders, a $315.00 USD or 250€ supplement applies along with fees for airport transfers)
Included
- 7 nights accommodation
- 6 days of riding
- All meals
- Wine with meals
- Airport transfers at pre set time
- Horse and all tack
- Guiding services
- Luggage transfers
- All local taxes
Not Included
- Airfare
- Travel Insurance
- Drinks outside of meals
- Gratuities for the staff at the end of the stay
Day 1: MADRID – SEGOVIA
Transfer from Madrid (pick up at 3pm) to Segovia, about a 1.5 hour drive. Your accommodation is at the Hotel San Antonio El Real (4*), a luxurious and charming hotel. It was built in the cloisters of an ancient monastery from the 15th century, in the heart of the city of Segovia, a 5 min walk from the Roman Aqueduct. After a chance to get settled into your room, you will transfer to the Equestrian Centre to see the stables and the horses. After meeting the horses, you’ll enjoy a panoramic visit of the city of Segovia by car and a welcome drink in the Segovia main square. Welcome dinner and night at the hotel Snã Antonio el Real, which has exquisite cuisine.
Day 2: SEGOVIA – LA GRANJA DE SAN ILDEFONSO
Your morning ride takes you from Segovia to the forest of Valsaín. You will follow old and famous trails, such as Cordel de Santillana and the Cañada Real Soriana to get to the source of water of the Roman aqueduct, following the reservoir waters and the Acebeda stream. Then following the Eresma River and the valleys that line it, you will arrive to the forest of Valsaín for a picnic lunch. These forests were traditionally hunting reserves for the kings of Castile and nowadays they are protected nature parks. In the afternoon, the ride winds its way to La Granja de San Ildefonso, where you will stay at the luxurious National Parador of La Granja 4*). A highlight includes a visit of the baroque palace and the gardens of this royal site, built in the times of Felipe V. Dinner and night at the Parador.
Day 3: LA GRANJA DE SAN ILDEFONSO – PEDRAZA, VILLA MEDIEVAL
From La Granja you will rejoin the Cañada Real , at the Caserio de Gamones. You will ride on the slopes of the Sierra de Guadarrama, until you get to Sotosalbos where you will enjoy the aperitivo stop and a visit of the Romanesque church from the 13th century. Riding through countryside of old oaks and through the small village of Requijada, you will arrive to your picnic stop, near the river Cega. In the afternoon, you will ride by the Ermita de Las Vegas, and follow the Cega river to Pedraza. This is a beautiful medieval village, with an imposing castle, charming cobbled streets and a charming main square. Dinner and night in the Hotel de la Villa, a 3* hotel in the heart of the village.
Day 4: PEDRAZA VILLA MEDIEVAL – CASTILLO DE CASTILNOVO
Today’s ride is a half-day ride. From Pedraza, you will follow ancient bridle paths through nearly abandoned rural villages, with a typical architecture built of stone and timber. You’ll stop for an aperitivo in the country and enjoy the unspoiled nature. Continuing the ride through open farming land, you will reach the plains where stands the imposing fortress of the Castle of Castilnovo, where you will finish today’s ride and have lunch. In the afternoon visit of the Castle and drive to the Duraton River Gorges and the jewel Ermita de San Frutos. Dinner and night at the hotel Vado del duration in Sepulveda.
Day 5: CASTILLO DE CASTILNOVO - PRÁDENA
After breakfast, the ride today follows the Duraron river, riding in the valley and the hill of los Cortos. You will stop for an aperitivo in Duraton villlage. Mounting back up you will ascent towards the Sierra to rejoin the Cañada Real (wide and open trail, excellent for long trots and canters) and arrive to a picnic lunch near Enebralejo. In the afternoon you will pass Enebralejo, where you can stop to visit the prehistoric caves. After that, the ride continues on to Pradena a typical mountain village. Dinner and night at the Posada del Acebo (“The Holly Bush Inn”, a typical house from the 18th century.
Day 6: PRÁDENA – COLLADO HERMOSO
Today you ride in the slopes of the Sierra de Guadarrama, in the Cañada Real, and trough the oak forest of Pradena. Your aperitivo stop is in the Cañada, which you will continue to follow until you get to Navafría, a mountain village with a timber production tradition. After a picnic lunch by the river Cega, the afternoon ride winds its way to Collado Hermoso. Dinner and night at the Posada Molino del Rio Viejo.
Day 7: COLLADO HERMOSO - SEGOVIA
In the morning, the ride passes through Santo Domingo de Pirón and Torrecaballeros before arriving to an early picnic lunch at the well preserved remains of an old ranch, where shepherds used to stop with their flocks to sheer the sheep, during the long journeys. The ride is short in the afternoon and carries you back to the stables in Segovia. Transfer to the hotel in Segovia where you will have a free afternoon to relax, walk around or explore. Dinner and night at a restaurant in Segovia. Night at the Hotel San Antonio el Real 4*.
Day 8: SEGOVIA - MADRID
After breakfast transfer to the Madrid airport, arriving there about 12 noon. All riders will be transferred at the same time. It is possible to arrange transfers at a different time but only if that is more convenient for the entire group.
Mary and Dave H.
Segovia at a Canter, in Spain, was an incredible adventure! My husband and I chose this trip to celebrate our 20-yr anniversary as Stacey had done such a great job coordinating our last ride through Italy back in 2019. Our overnight stays in this Spain ride included staying in charming, medieval towns with great views of castles, and eating at some really interesting restaurants in olde world style (Segovia is really cool). Our guide, Ana, did an outstanding job guiding us through beautiful scenery, educating us on the fascinating history of each area and accommodating when we needed to rest! Also, if you like to eat, they feed you a lot of delicious food on this trip and would have a special helper who would meet us mid-ride with wonderful meals and food for the horses who deserved a nice break. This ride is certainly for the advanced intermediate/expert level riders and you will get to do your share of canter/gallops through many fields and ancient bridal paths. It is evident that their horses are well loved, well-behaved and in excellent shape as we rode a minimum of 18 miles a day. We are grateful to all who mindfully coordinated this trip and to Stacey for listening to what we wanted for our special celebration!