Ride South Africa with me
In partnership with
Join me for a once-in-a-lifetime cycling adventure in South Africa.
Why Join
This isn’t a sufferfest with your head down chasing miles all day. If you want relentless, full-gas riding with no let-up, this probably isn’t for you. But if you want big, rewarding days on the bike mixed with everything South Africa does brilliantly - wine, wildlife, proper scenery - then this is a very good balance of both.
Highlights
This is not your standard cycling trip. It is a carefully built experience that combines world-class riding with everything that makes South Africa unforgettable. From iconic routes and big days on the bike to wildlife, culture and scenery, these are the moments that make this trip stand out.
Ride World-Class Routes in South Africa
Take on some of the most spectacular cycling roads on the planet, from sweeping coastal routes to the iconic climbs of the Western Cape. This is proper riding, not just ticking over the legs on holiday.
A Proper Adventure, Not Just a Bike Trip
This is 10 days of riding, exploring and experiencing South Africa at its best - Cape Town, wine country, mountains and more. You are not just training, you are fully immersed in the place.
From Bike to Big 5 Safari
what you get from me
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I’ll be riding the full route with you
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Daily briefings so you know exactly what’s ahead
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A signed copy of all 7 of my books
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Help with pacing, mindset, and getting through the tougher moments
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Free coaching on improving your cycling in the leadup
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Advice on nutrition and endurance as we go
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Time in the evenings to chat, ask questions, and share stories
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Finishers medal
You’re not just booking onto a trip. You’re getting direct access to everything I’ve learned from years of pushing limits.
Tour Schedule
Cape Town
Cape Town is a port city on South Africa’s southwest coast, on a peninsula beneath the imposing Table Mountain. Slowly rotating cable cars climb to the mountain’s flat top, from which there are sweeping views of the city, the busy harbor and boats heading for Robben Island, the notorious prison that once held Nelson Mandela, which is now a living museum.
Tue, 2nd March
Airport to Hotel Transfer
Monte Vista Boutique Hotel
Tue, 2nd Mar - Sun, 7th Mar
For a three-day cycling escape through the Robertson Wine Valley and Langeberg Mountains, the 4-star Monte Vista Boutique Hotel in Montagu serves as the ultimate luxury basecamp. Its central location on historic Church Street provides immediate access to iconic routes like the Cogmanskloof Pass and the rolling climbs toward Koo Valley.
After high-mileage days, cyclists can store gear securely before retreating to "Afri-chic" en-suite rooms equipped with private verandas and air conditioning. The property features two outdoor swimming pools set within an acre of manicured gardens, perfect for post-ride muscle recovery. To ensure a seamless experience, the hotel’s backup power system keeps your GPS and gear charged during loadshedding.
Start each morning with a hearty, locally sourced breakfast at the on-site restaurant to fuel your ascent. With its blend of heritage charm and modern comfort, Monte Vista offers a sophisticated sanctuary for riders exploring the rugged beauty of the Western Cape.
Tue, 2nd March
Welcome Dinner
Dinner at Charlestons at the Montagu Country Hotel is a nostalgic, elegant experience set in a beautifully restored Art Deco dining room. With soft jazz playing in the background and vintage decor all around, guests enjoy classic South African dishes with a modern twist - often featuring local produce and regional wines. The ambiance is warm and refined, evoking a sense of old-world charm that perfectly complements the relaxed pace of Montagu.
Wed, 3rd MarCh
Cycle: The Koo Valley
The Koo Valley Cycle Route is a scenic ride through one of the Western Cape’s most beautiful fruit-growing regions. Winding past orchards, vineyards, and farmland framed by the towering Langeberg and Hex River Mountains, the route offers cyclists a mix of gentle stretches and more challenging climbs. Along the way, riders are treated to panoramic views, seasonal blossoms or autumn colors, and fresh country air that makes the experience both invigorating and serene. It’s a route that combines natural beauty with rural charm, making it a rewarding outing for both leisure cyclists and those seeking a bit more adventure.
The Koo Valley Cycle Route is a challenging ~100 km out-and-back ride with around 1,500 m of total elevation gain, featuring two major climbs over Burgers Pass (Koo Pass) and Rooihoogte Pass. The outbound leg steadily ascends through rolling farmland into steeper gradients on the passes, before rewarding riders with a long, fast descent back toward Montagu - making it both a tough endurance test and an exhilarating ride.
Thu, 4th March
Cycle: The Tradouws
The Tradouws Cycle Route takes riders through one of the Western Cape’s most scenic mountain passes - Tradouws Pass, which links Barrydale and Swellendam. The route combines rolling farmlands, vineyards, and orchards with the dramatic switchbacks and sheer cliffs of the pass itself. Cyclists face a steady climb with moderate gradients, rewarded by sweeping views of rugged rock faces, gorges, and green valleys below. The descent on the opposite side offers flowing corners and exhilarating speed, though it requires careful control. With a mix of endurance climbing and fast downhill stretches, the Tradouws route is both visually spectacular and physically rewarding.
The Tradouws Cycle Route stretches roughly 160 km and features a substantial 1,870 m of total climbing, making it the longest and one of the most demanding stages in the Cape Classic series. A highlight is the ascent of Tradouw Pass - a paved, scenic climb through the Langeberg over 14–17 km, with an elevation gain of about 219 m. The climb is most intense in the early kilometres, with gradients reaching up to around 10%. After cresting the pass, the route undulates through valleys and rolling terrain before descending and climbing again on “Op de Tradouw” - overall delivering a sustained, endurance-testing profile that rewards perseverance with dramatic mountain vistas and flowing descents.
Fri, 5th March
Cycle: Robertson - Bonnievale loop
The Robertson–Bonnievale Loop is an 80 km ride with about 540 m of total climbing, making it a moderate and rewarding route. Following mostly quiet, paved country roads, it winds through vineyard-covered valleys, farmlands, and along stretches of the Breede River. With gentle ascents and rolling terrain, it offers a steady workout while showcasing the region’s tranquil wine country scenery - an ideal blend of cycling effort and scenic charm.
The Robertson–Bonnievale Loop covers around 80 km with a total elevation gain of roughly 530–540 m, classifying it as a moderate rolling route rather than a mountainous stage. The profile is characterized by short, gradual climbs averaging 2–4%, rarely exceeding 6%, spread evenly throughout the loop. Elevation changes are frequent, with a mix of undulating rises in the first 30 km leaving Robertson, steady rollers through the mid-section toward Bonnievale, and a gentle net descent on the return leg. With no single sustained climb, the challenge comes from the cumulative effect of repeated hills, making it a perfect endurance ride to maintain steady power output while enjoying flowing vineyard and valley terrain.
Sat, 6th March
Let the legs recover
Game Viewing: Aquila Private Game Reserve
A game drive at Aquila Private Game Reserve is a classic safari experience that brings you up close to Africa’s most iconic wildlife, just a couple of hours from Cape Town. Setting out in an open 4x4 vehicle with an experienced guide, you’ll traverse the reserve’s diverse landscapes of mountains, valleys, and bushveld in search of the Big Five: lion, elephant, buffalo, rhino, and leopar, alongside giraffe, zebra, hippo, and an array of birdlife. The drives are both educational and exciting, as guides share insights into animal behaviour, conservation, and the surrounding ecosystem. Morning drives often include a coffee stop with breathtaking views, while afternoon safaris may end with a sundowner as the sky turns golden over the Karoo.
Lunch at Aquila Safari Lodge
Lunch at Aquila Safari Lodge is a relaxed yet refined experience, set against the backdrop of the Karoo’s dramatic landscapes. Guests can enjoy a generous buffet featuring a mix of local South African flavours and international dishes, often highlighting fresh, seasonal produce. Whether dining indoors in the African-style lodge or outside on the terrace overlooking the reserve, the atmosphere is warm and welcoming. It’s a perfect moment to unwind after a game drive - sharing stories, savouring good food, and soaking up the views before heading out on your next adventure.
Sun, 7th March
Cycle: Montague to Wellington (incl. Bain’s Pass)
The ride from Montagu to Wellington via Bain’s Kloof Pass is a spectacular and rewarding cycling experience that showcases the raw beauty of the Western Cape. Beginning in the serene farmlands of Montagu, the route winds through vineyard-covered valleys and open countryside before climbing the legendary Bain’s Kloof Pass - a historic and scenic mountain pass known for its sweeping views, lush greenery, and winding roads. With every turn, the landscape shifts from rugged peaks to rolling hills, offering a mix of challenge and exhilaration. The descent into Wellington is fast and thrilling, ending the ride with a satisfying sense of accomplishment amid the tranquil charm of the Cape Winelands.
Cycling from Montagu (±220 m) to Wellington via Bain’s Kloof offers mostly flat riding through the Breede Valley before the real test begins. The climb up Bain’s Kloof rises from about 200 m to 594 m over 10 km, with steady 5–7% gradients and steeper switchbacks near the top. From the summit, it’s a rewarding descent of nearly 500 m into Wellington (±120 m). The route combines long endurance stretches with one sustained mountain pass effort and a fast, technical downhill.
Lunch at Diemersfontein Wine Estate
Refresh with a relaxing shower followed by a leisurely lunch at Diemersfontein Wine Estate, surrounded by vineyards and mountain views. Enjoy award-winning wines and farm-to-table cuisine in a serene countryside setting.
Lunch to Hotel Transfer
The Commodore Hotel
Sun, 7th Mar - Thu, 11th Mar
A stay at The Commodore Hotel in Cape Town offers a refined blend of nautical elegance and modern comfort, set in the heart of the vibrant V&A Waterfront. The hotel's maritime-inspired interiors, with polished wood finishes and naval artwork, reflect Cape Town’s rich seafaring heritage. Each room is thoughtfully designed with air-conditioning, complimentary Wi-Fi, USB charging points, and en-suite bathrooms for a relaxed and comfortable stay.
The Commodore features a range of facilities to enhance your visit, including a peaceful outdoor pool area, a fully equipped gym, and the award-winning Casuarina Wellness Centre. The Clipper Restaurant serves a diverse menu of South African and international cuisine, paired with an excellent local wine selection, while the Admiralty Bar offers a laid-back atmosphere for drinks. With its unbeatable location, guests are just steps away from Cape Town’s top attractions, including the Zeitz MOCAA, Robben Island ferry, and the shops, galleries, and restaurants of the V&A Waterfront.
Dinner
Experience your first dinner at the iconic V&A Waterfront, where vibrant energy meets stunning harbor and Table Mountain views. Choose from a variety of top restaurants offering fresh seafood and South African flavors in a lively, scenic setting.
Mon, 8th Mar
Let the legs recover
Tour - Cape Town & Table Mountain
Cape Town, founded in 1652 by the Dutch East India Company, grew as a key port for ships traveling between Europe and the East Indies. Over time, it came under Dutch and British control, becoming a melting pot of cultures. The city played a central role in the struggle against apartheid, serving as a hub for resistance movements.
Table Mountain, an iconic natural landmark, is a symbol of Cape Town. Its flat top and ancient geological origins make it a defining feature of the city. Today, it attracts tourists with its stunning views and historical significance, having been a site for early exploration and defense.
Wine Tasting
Wine tasting in Cape Town is a refined yet relaxed experience, set against some of the world’s most picturesque vineyard landscapes. The Cape Winelands -most notably Stellenbosch, Franschhoek, and Paarl - are within an hour’s drive of the city, offering rolling vineyards framed by dramatic mountain ranges. Tastings usually involve guided flights of carefully selected wines, from crisp Sauvignon Blancs and Chenin Blancs to bold Shiraz and elegant Cape blends, often paired with artisanal cheeses, chocolates, or fine dining. Many estates blend centuries-old Cape Dutch heritage with cutting-edge winemaking, giving visitors both history and innovation in a single sip. With modern cellar doors, panoramic terraces, and knowledgeable sommeliers, Cape Town wine tasting is as much about the scenery and storytelling as it is about the wines themselves.
Tue, 9th March
Cycle: Cape Town to Cape Point Return Route
The Cape Town to Cape Point return ride is a classic Peninsula loop that combines stunning coastal scenery with varied elevation. Leaving Cape Town, the route climbs steadily over Edinburgh Drive before dropping into the False Bay side, where riders enjoy rolling terrain through Muizenberg, Kalk Bay, and Simon’s Town. From there, the long drag up Smitswinkel tests endurance as you approach the entrance to Cape Point. Turning back, the ride follows the Atlantic coastline, taking in the sweeping ascent of Chapman’s Peak and the short but steep sting of Suikerbossie before descending into Camps Bay and finishing along the flat, fast stretch back to the city. Overall, the profile alternates between sustained climbs, coastal rollers, and exhilarating descents, making it a true test of both strength and pacing.
The Cape Town to Cape Point return route is a demanding endurance ride of roughly 130–150 km with an accumulated elevation gain of 1,800–2,000 m. The profile is characterised by a sequence of long, gradual coastal climbs punctuated by sharp ascents over the iconic Atlantic seaboard passes. Riders first contend with Chapman’s Peak Drive, a steady climb averaging around 4–5% gradient over 4.5 km, followed by undulating rollers toward Simon’s Town. Approaching Cape Point, gradients kick up again with sustained sections at 6–7%, before the turnaround descent. The return amplifies cumulative fatigue, with another crossing of Chapman’s Peak and additional elevation via Ou Kaapse Weg or the coastal alternative. The profile is highly variable—continuous elevation gain without extended flat recovery - making it a classic test of climbing efficiency, pacing strategy, and endurance conditioning.
Wed, 10th March
Robben Island Tour
Catch the Robben Island ferry and embark on a guided tour of the island.
Two Oceans Aquarium Visit
Visit the acclaimed Two Oceans Aquarium.
Farewell Dinner
Enjoy a memorable farewell dinner at a scenic waterfront restaurant at the V&A Waterfront, with views of Table Mountain and the harbor. Savor local cuisine and fresh seafood while soaking in the vibrant atmosphere and live music.
Thu, 11th March
Relaxation & Departure
Enjoy a leisurely Breakfast at the hotel before your final packing and check-out.
Hotel to Airport Transfer
Secure Your Place
Total per person
£5,995
Single Supplement £750
Based on two people sharing a double room throughout
What's included
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9x Nights Accommodation
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All Private Road Transfers
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5x Days Cycle Operations & Logistics
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All Meals (where stated)
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Aquila Safari Day Trip (inc. lunch)
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Best of Cape Town Tour & Wine Tasting
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Robben Island & Table Mountain Tour
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Cycle Jersey
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All Local Taxes & Fees
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Welcome pack from Sean
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Finishers Medal
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Cycle coaching in the leadup
Not included
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International flights
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Any Domestic Flights
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Bike Hire
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Travel insurance
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Bar Drinks
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Personal Expenses
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Tips
