Sample itineraries

Sample itineraries

Get a feel for the routes, scenery, wine estates and other venues you will enjoy on your riding holiday

The following sample itinerary outlines the type of rides, wine tastings and other local excursions on offer at Cape Winelands Riding, situated in the centre of the triangle created by the three world-famous wine regions of Paarl, Franschhoek and Stellenbosch in the Western Cape.

Let us plan your perfect holiday


On arrival we will sit with guests and plan an itinerary to suit tastes, also taking into account the level of riding experience, size of group and preferred length of stay.

Unless otherwise arranged, meals are at quality local restaurants with either a set menu or à la carte. These restaurants have been carefully selected for your enjoyment and showcase the food and wine the region has become so famous for.

Sample itinerary

These are strictly sample itineraries. Excursions are subject to seasonal changes and are always weather dependent.  Your riding program will be determined by your date of arrival and the length of your stay.

Day 1

After your arrival and once you have settled into your accommodation, we will take you for a short, gentle ride in the afternoon, giving you a feel for your horse and the general surroundings.  Then, back at your accommodation, enjoy poolside sundowners or relax in the hammock outside your room before experiencing local cuisine at its best at one of the top restaurants in Franschhoek / Paarl complemented by award-winning local wines.

Day 2

After breakfast, we saddle up and head into local vineyards and orchards, stopping for a brief break at a point offering incredible photo opportunities with the magnificent Paarl Valley stretched out below. We then head along the foot hills of Simonsberg Mountain towards Anura Wine Estate, a route on which you can give your horse its head and enjoy a canter between the vines and along charming old farm roads.  At Anura, enjoy a wine tasting before strolling over to the charming Estate restaurant for an à la carte lunch with your preferred wine. We head home at a leisurely pace after a lazy lunch, arriving back at the yard around 4pm.  There’s time to relax before dinner which is a culinary showcase of traditional Cape cuisine prepared by local chefs.

Day 3

Now acclimatized and comfortable with your horse, another full day’s ride starts with a spectacular mountain ride through refreshing eucalyptus and pine forest.  You will have ample opportunities to take photos of the panoramic views across the Paarl and Franschhoek Valley.  Stopping at Backsberg, another internationally-acclaimed vineyard and the first carbon neutral wine estate in South Africa, there’s time to sample excellent wines that are produced on this popular estate. After the wine tasting lunch is in the beautiful garden restaurant or by a cozy log fire depending on the weather. We then head back, riding through vineyards and plum orchards, enjoying more spectacular views across the Paarl and Franschhoek Valley and over the dramatic Drakenstein mountain range.  Back at the yard you can relax with a drink on the patio before your transfer to your accommodation.  If you are staying in our farm accommodation you are welcome to wander around the property and meet the rest of our horses or just relax in the hammock after a long day in the saddle.  Dinner is at a local restaurant in either Paarl, Franschhoek or the Stellenbosch region.

Day 4

Today’s morning ride takes you into more unspoiled terrain in the district, through new orchards, vineyards and along estate dams. Riders can set their own pace but whether it’s a fast canter or lazy meander, it’s another exhilarating morning on horseback followed by lunch at another winery. Without an afternoon ride today, guests can relax at their accommodation or amble through the historical towns of Stellenbosch, Franschhoek or Paarl, a 10- to 20-minute drive away, or play nine holes at the local golf course. Dinner is at a local restaurant giving you another taste of local fine dining and wines – an experience on a par with the best international restaurants.

For those wanting to venture further afield today, other full-day excursions can be arranged. Please note that these optional activities are charged extra. Some of the most popular one-day excursions are:

  • Beach ride and lunch along the coast
  • Cape of Good Hope – full day sightseeing following the peninsula coastline with a visit to a protected African penguin colony and, of course, the famous Table Mountain
  • Shark Cage Diving – a day for the true adrenaline junkie

The day ends back at your accommodation and then it’s another relaxed evening sampling fine local food and wines.

Day 5

Another full day ride awaits as we start out towards the Eastern side of Simonsberg, taking in the now familiar beauty that surrounds us.  After a slow, long canter through a lane of majestic eucalyptus trees we reach an air strip where you can choose to have an exhilarating gallop. After settling our horses we continue our ride, following the contours of the vines high on the Eastern slopes of Simonsberg before descending to the old-world charm of our lunch stop, Plaisir de Merle.  Dating back to 1693, this magnificent farm produces world-class wines which we’ll enjoy under giant oak trees, paired with a platter of local cheese and cold meats. The ride home is a relaxed meander through peach and plum orchards and, back at the yard, there is time to enjoy a drink on the patio before retiring to your accommodation.  Dinner tonight is a traditional barbecue (Braai) at the stables. This is an informal evening hosted by Louis and Ellen, enjoyed with more excellent wines from local estates.

Day 6

Waking up to another beautiful day in the Cape Winelands, we are ready to take you on picturesque forest ride through pine and eucalyptus trees. After an exciting fast uphill canter you are rewarded with sweeping views over the plains and wheat fields of the West Coast with Paarl Mountain, Paardeberg and Kasteelberg in the far distance. Listen to the birds as you ride along forest trails and, if you are lucky, you may spot a Duiker in the forest shadows. After returning to the stables you will be treated to lunch at a local winery and then back to the yard for a late afternoon ride before heading back to your accommodation.  At dinner, you will again be spoiled with local cuisine at one of the top local restaurants in the valley.

Day 7

On your last morning with us we are determined to add a few more lasting memories before you leave our beautiful valley. We take you for an exhilarating ride through the vineyards and orchards before it is time to say good bye. After check-out we will transfer you to the airport.  If you have an evening flight we can take you through to the V & A Waterfront for last minute shopping and sightseeing.

Looking for a different kind of horse riding holiday?

We also offer an exclusive trail, The Cape Gourmet Wine Trail which has a similar itinerary on certain days. Only two trails are planned every year and space is limited to eight riders. Booking well in advance is recommended. If you are a foodie and wine lover with a passion for horses and magnificent scenery, this is a must!

Learn more > The Cape Gourmet Wine Trail