317 days to go

South African Cape Cycle Expedition with Sean Conway

2nd - 11th March 2027

Your Host - Sean Conway

Sean Conway is one of the world’s most accomplished endurance adventurers, renowned for pushing the limits of human performance and inspiring others to do the same. A bestselling author, motivational speaker and ultra-endurance athlete, Sean is the only person to have completed a self-powered triathlon of Great Britain, swimming, cycling and running the length of the country. His extraordinary challenges have included cycling around the world, running the length of Britain, and numerous record-breaking endurance feats that demonstrate resilience, mental strength and relentless determination.

As leader of this exclusive sports expedition to South Africa, Sean will bring his trademark energy, humour and mindset coaching to the group. Participants will gain first-hand insight into goal setting, performance under pressure and the power of pushing beyond perceived limits, all set against the spectacular sporting landscapes of South Africa. This is a rare opportunity to train, learn and be inspired by a true endurance icon.

About your itinerary

This unique 10-day adventure through South Africa is a dream blend of cycling, culture, safari and unforgettable landscapes.

Participants will be immersed in the charm of Montagu for the first three days of rides through vast vineyards, quiet country roads, and striking mountain passes. Each day includes iconic Cycle routes, following the world renowned Cape Argus Cycle Event and covering 109km with a combination of challenging sections and showcasing the stunning coastal views and Cape Town scenery of the Western Cape.

Between the saddle time, you'll recharge with a Big 5 safari at Aquila, soaking in the thrill of spotting wildlife in their natural habitat before returning to Montagu’s peaceful pace. The journey continues with a ride over the iconic Bain’s Kloof Pass into wine country, a taste of Diemersfontein hospitality and a transfer to Cape Town's vibrant V&A Waterfront.

From cycling the world-famous Atlantic Seaboard to Cape Point, to wine tasting and city exploration, this expedition is filled with iconic moments.

This is more than just a cycling trip — it’s a full-sensory journey through the heart and soul of South Africa.

Trip Purpose & Vision

The expedition is designed for senior executives seeking meaningful leadership growth, physical challenge, and purposeful impact. Set against Cape Town's breathtaking natural landscapes, this journey blends endurance cycling with powerful reflection, community connection, and team development. This is more than a trip — it’s a transformative experience that unites challenge, culture, and contribution.

Social Impact Cause

This Cycle Expedition will be raising funds for the Sean Conway Academy, which supports Youth Sport within Schools across the UK.

Book your place today!

Get in touch to secure your place...

Dom Webb

dom@orbis-expeditions.com

07717 688 994

Highlights of this trip

Highlights of this trip

Cycle some of the Western Cape’s most scenic routes

1/6
Highlights of this trip

Conquer the legendary Bain’s Kloof Pass

2/6
Highlights of this trip

Experience the famous Cape Town Cycle Tour route

3/6
Highlights of this trip

Explore Cape Town’s sights & enjoy wine tasting

4/6
Highlights of this trip

Spot the “Big 5” on an African safari

5/6
Highlights of this trip

Visit a Rugby development club with some SA Rugby legends

6/6

Itinerary

Not in use (below desc displays under price)

Loading.....