South Africa Winelands Bike Tour

Your guides will meet you at the Cape Town waterfront early this morning. After a bike fitting and safety briefing we set out for our first ride toward Jonkershoek, a nature reserve occupying a dramatic valley near the major wine destination of Stellenbosch. Some say that South African mountain biking was born right here, since the trails in this preserve launched the sport’s popularity. We’ll enjoy a post-ride lunch at our favorite little cyclist café. A short transfer or hilly extra ride brings us to Clouds Estate—our hotel and working wine farm surrounded by the dramatic Simonsberg and Drakenstein mountains. A special treat awaits our arrival: one of our favorite winemakers, Johan, will lead us through an introductory tasting of South Africa’s most celebrated wines. Tonight we dine among the vines at a family-owned estate recognized as one of the best in the Cape Winelands. Chef Caroline Coetzee’s food is complemented by local artwork on display in her restaurant—an all-around showcase of South African talent.

Meals: Lunch / Dinner
Destination: Jonkershoek, Helshoogte
Accomplished: 16 miles / 26 km, elevation gain: 1,788 feet / 545 meters
Longer Option: 24 miles / 40 km, elevation gain: 2,870 feet / 875 meters
Accommodation: Clouds Estate or De Zeven Guest Lodge

Today we ride to Boschendal Wine Estate on bike trails beloved by local cyclists and pros alike—they’ve even hosted South Africa’s Cape Epic mountain bike race. But don’t be intimidated, today’s ride lends itself to cyclists of all levels: choose to rack up miles in the saddle or take it easy and treat yourself to an extra glass of wine (or wyn in Afrikaans), if you prefer. Either way, explore the country’s complicated history as we pedal on single tracks through the vineyards, passing pristine manors juxtaposed with humble agricultural villages. In the werf, or farmyard, we’ll have an al fresco lunch at a local woman’s home where we’ll try traditional roosterbood. This evening we’ll head into the historic town of Stellenbosch—one of the country’s first Dutch settlements and a treasure trove of colonial architecture—for a stroll through its oak tree-lined streets and dinner at one of our favorite restaurants.

Meals: Breakfast / Lunch / Dinner
Destinations: Helshoogte, Kylemore, Boschendal, Stellenbosch
Accomplished: 21 miles / 34 km, elevation gain: 1,391 feet / 424 meters
Optional Extra: 26 miles / 43 km, elevation gain: 2,070 feet / 631 meters
Accommodation: Clouds Estate or De Zeven Guest Lodge

This morning, our transfer brings us to the trails of Bottelary Hills Conservancy: an immaculately maintained network of mountain biking routes connecting nearly 40 local vineyards. Great pains were taken to preserve the native flora, including fruit orchards, lilies, and fynbos (a type of vegetation unique to South Africa). Our ride rewards us with views all the way to Table Mountain, and we’ll stop for a picnic lunch at the Jordan Wine Estate. Spend the rest of the evening at an informal South African settlement, getting to know the local personalities during a walking tour. After, we’re invited to dinner with the locals as they share their food, stories, music, and traditions with us over the course of an unforgettable evening.

Meals: Breakfast / Lunch / Dinner
Destinations: Bottelary Hills, Stellenbosch
Accomplished: 16 miles / 26 km, elevation gain: 1,738 feet / 530 meters
Longer Option: 36 miles / 45 km, elevation gain: 3,284 feet / 1,001 meters
Accommodation: Jordan Wine Estate

As we pedal out of Stellenbosch this morning, we may cross paths with the South African pheasants called tarentaal as they scurry noisily through the vines or eagles manning their posts, protecting the vineyards from predators. Early European settlers realized the appeal of these peaceful foothills and their exquisite terroir, and the countryside remains some of the most coveted real estate on the continent. Just ask golfer Ernie Els, who scooped up a Western Cape winery where we’ll have lunch paired with estate wines. This afternoon, check into our final hotel: the luxurious Tintswalo Atlantic, located at the base of Table Mountain National Park. Dine at the hotel restaurant and soak up the sea views, or head into Hout Bay for dinner on your own.

Meals: Breakfast / Lunch
Destinations: Raithby, Hout Bay
Accomplished: 19 miles / 32 km, elevation gain: 1,430 feet / 436 meters
Accommodation: Tintswalo Atlantic or Newmark Future Found Sanctuary

Enjoy a laid-back morning before hopping on the bike for a final day of cycling. The road to Chapman’s Peak is considered the country’s most beautiful byway, so our ride over the peninsula includes plenty of photo stops. Our destination today is the quaint fishing village of Kalk Bay, its harbor of vocal sea lions basking in the warm sun and local fishermen selling this morning’s fresh catch. A lunch of fresh seafood is only fitting! Choose to take it easy for the rest of the afternoon—maybe checking out the colorful beach cottages—or keep on riding back to Tintswalo. For our final night, it’s sundowners and dinner on the deck as we toast to our wonderful week together.

Meals: Breakfast / Lunch / Dinner
Destinations:  Chapman’s Peak, Kalk Bay
Accomplished: 21 miles / 34 km, elevation gain: 1,919 feet / 585 meters
Longer Option: 29 miles / 47 km, elevation gain: 3,483 feet / 1,062 meters
Accommodation: Tintswalo Atlantic or Newmark Future Found Sanctuary

Spend your final morning in South Africa as you wish, whether you prefer to sleep in late or take a short hike to get your endorphins for the day. Before our guides bid you farewell, transfer with them to Cape Town International Airport or right into the city for those adding additional days to their trip.

Meals: Breakfast
Destinations: Kalk Bay