Spain with Richard Dunwoody:
7 to 11 October 2026

Richard Dunwoody is one of racing’s great names. He became the only jockey of his generation to win the ‘Big Three’ National hunt races, was Champion jockey from 1993 to 1995 and rode 1699 winners in Britain alone. Having achieved so much in racing, he turned to adventure, undertaking expeditions for charity and travelling widely to pursue his other passion, equestrian photography. He’s ridden in Mongolia, Kyrgyzstan, Transylvania, Ecuador and Namibia to mention just a few. Now you can join him and our wonderful guiding team, getting to know historic Segovia in Spain, Richard’s home turf and the perfect destination for a short autumn escape.

Where is it?

Based out of the historic city of Segovia, to the north of Madrid in central Spain.

What is it like?

Segovia is a UNESCO World Heritage Town with a magnificent cultural heritage that includes the awe inspiring 1st Century AD Roman aqueduct, the spectacular Alcazar fortress, and miles of accessible, open countryside stretching to the Sierra de Guadarrama. A buzzing university hub, it’s big enough to boast lively squares, interesting shops and numerous restaurants, yet small enough to be easily negotiated on foot. Accommodation on this ride includes 2 nights close to the 18th C Royal Palace at La Granja, a few kilometres from Segovia, and 2 nights in central Segovia, at the comfortable Parador. Each day will be carefully organised with a varied riding route to allow a ‘sporty’, energetic pace, a break for aperitifs and tapas, a long lunch in traditional Spanish style and a relaxing dinner at a hand-picked restaurant, enjoying good company, good food, wine and conversation.

Who does it suit?

Confident, capable riders who love energetic riding, appreciate comfortable accommodation, and want to join a small group with dedicated, knowledgable and entertaining hosts. Your local guide Ana and her team are fun, well-informed and professional. Richard is charming, easy going and entertaining company. They all know Segovia well – and it’s a beautiful, historic city to visit. Whether you’re a racing enthusiast, an adventure enthusiast or just want a few days of fun, good quality riding with interesting companions who’ve done numerous different and exciting things in their lives, this will make a perfect autumn escape.

Why we love it

A proper and refreshing escape, in just 4 days. Richard’s life of challenge, achievement and adventure has lead him to become a motivational speaker, a wonderful photographer and an all-round inspiring companion and he knows Segovia well. He’s good fun, good company and full of interesting stories. You’ll come back from this exhilarated, hugely entertained and may have learnt a little history too – without having to arrange a thing yourself.

Travel with trust

When you travel with Ride World Wide, you can travel with trust. We’re a member of ABTOT (the Association of Bonded Travel Organisers Trust) which provides financial protection for your booking through our ABTOT bond and under the ABTOT ATOL franchise. If you have any questions please ask.

In a Nutshell

Riding
5 hours a day
Horses
Andalucian cross, Anglo-Hispanos, Lusitano crosses
Pace
Moderate overall with energetic canters
Riding Ability
Intermediate to experienced
Weight Limit
90kg (14st 2lbs)
Group Size
Maximum 10 plus host
Accommodation
3* to 4* hotels and Parador
2026 Dates
7 to 11 October 2026
2026 Prices
1700 Euro per person sharing
What you'll be doing

Itinerary in Brief

Below is an example itinerary. Please ask us for other itineraries.

Day 1

Met at about 15.00 at Madrid international airport and driven about 1 1/2 hours to a small hotel close to the Royal Palace at La Granja, a few kms from Segovia. Meet Ana your riding your guide at the hotel and, if time, a short drive to the stables, then back to the hotel for a welcome dinner and the night.

Day 2

Breakfast and a chance to visit the gardens of the baroque Royal Palace before being collected at about 10.00 for a short drive to the stables. Mount up and once settled, head off riding along cattle drovers tracks. At about midday, meet the back up team for aperitifs and after riding on for a couple of hours, a lunch break at about 14.00. After a leisurely lunch and short siesta, ride through the Valsain forest, getting back to the stables in the late afternoon. Short drive back to the hotel. Drinks, dinner and night La Granja

Day 3

Breakfast and collected at about 10.00. Short drive to meet the horses, then head off riding in a different direction with plenty of chances for exciting canters. A break mid-morning for aperitifs, and ride on until you meet the back up for lunch close to the La Granja polo field. Continue riding after lunch, along the west side of Ponton lake, arriving back at the stables at about 17.30. Short drive to the Parador of Segovia. Settle in, meet for drinks, then dinner. Night Parador of Segovia.

Day 4

The last riding day heading off after breakfast following the Eresma River canyon. Aperitif stop and plenty of canters with views of the Cathedral of Segovia, Alcazar and historic town. Lunch with wonderful views of the city skyline and Alcazar before riding back through the outskirts of the town to arrive at the stables late afternoon. After riding you might arrange a massage (extra charge) or head into town for a drink in the square by the Cathedral before dinner at a restaurant in town. Night Parador of Segovia.

Day 5

Breakfast and group transfer back to Madrid arriving about 12 noon in time to check-in for onward flights.
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