Tour overview

This 12-day cycling holiday loops through the vineyards, mountains and coast of the Western Cape. A tour leader rides with the group, which numbers between four and fourteen, with a support vehicle. You stay eleven nights in three- and four-star hotels, guesthouses and lodges, most with pools, with breakfast daily and a welcome dinner.

From Cape Town you ride over Hellshoogte to Stellenbosch and climb the Franschhoek Pass, then head into the semi-arid Karoo and through the Langeberg Mountains to Bontebok National Park.

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You reach Cape Agulhas, the southernmost point of Africa, and ride to Hermanus for a free day of whale watching. The Whale Coast to Gordon's Bay, a ride around the Cape Peninsula with its penguin colony, and Chapman's Peak bring you back to Cape Town.

The physical rating is medium. This trip suits keen cyclists who want great riding with wine and wildlife.

Trip highlights

  • Stellenbosch (Day 2)
  • The Franschhoek Pass (Day 3)
  • The Little Karoo (Day 4)
  • Cape Agulhas (Day 6)
  • Hermanus (Day 8)
  • Chapman's Peak (Day 11)

Your route

15 stops from Cape Town to Cape Town

12-day route: Cape Town – Stellenbosch – Montagu – Karoo – Swellendam – Arniston – Hermanus – Gordon's Bay – Cape Town
  1. Cape Town Day 1
  2. Bloubergstrand Day 2
  3. Stellenbosch Day 2
  4. Franschhoek Day 3
  5. Montagu Day 3
  6. Barrydale Day 4
  7. Swellendam Day 5
  8. Cape Agulhas Day 6
  9. Arniston Manor House Day 6
  10. Hermanus Days 7–8
  11. Betty's Bay Day 9
  12. Simon's Town Days 9–10
  13. Cape Point Day 10
  14. Hout Bay Day 11
  15. Cape Town Days 11–12

Why choose this tour

The Western Cape's best riding. A support vehicle every day.

Best suited to

  • Keen cyclists
  • Wine lovers
  • Active travellers
  • Solo travellers
A cyclist riding a road between vineyards

Day-by-day itinerary

12 days from Cape Town, South Africa to Cape Town, South Africa

  1. Day 1 · Cape Town Cape Town

    A welcome dinner.

    Hotel
    City Lodge V&A Waterfront
    Meals
    Dinner
  2. Day 2 · Hellshoogte, Stellenbosch Stellenbosch

    Through the vineyards.

    Hotel
    Stellenbosch Hotel
    Meals
    Breakfast
  3. Day 3 · Franschhoek Pass, Montagu Franschhoek Pass

    A mountain pass.

    Hotel
    Montagu Hotel
    Meals
    Breakfast
  4. Day 4 · Little Karoo Karoo

    A semi-desert.

    Hotel
    Karoo Art Hotel
    Meals
    Breakfast
  5. Day 5 · Langeberg Mountains, Bontebok National Park Bontebok

    Over the mountains.

    Hotel
    Aanhuizen Guest House
    Meals
    Breakfast
  6. Day 6 · Cape Agulhas, Arniston Cape Agulhas

    Africa's southern tip.

    Hotel
    Arniston Manor House
    Meals
    Breakfast
  7. Day 7 · Elim, Hermanus Hermanus

    A craft beer stop.

    Hotel
    Windsor Hotel
    Meals
    Breakfast
  8. Day 8 · Hermanus Hermanus

    A free day.

    Hotel
    Windsor Hotel
    Meals
    Breakfast
  9. Day 9 · Whale Coast, Gordon's Bay Whale Coast

    A coastal ride.

    Hotel
    Quayside Hotel
    Meals
    Breakfast
  10. Day 10 · Cape Point, Boulders Beach Cape Peninsula

    Penguins.

    Hotel
    Quayside Hotel
    Meals
    Breakfast
  11. Day 11 · Chapman's Peak, Hout Bay, Camps Bay Cape Town

    A famous ride.

    Hotel
    City Lodge V&A Waterfront
    Meals
    Breakfast
  12. Day 12 · Cape Town Cape Town

    The trip ends.

    Meals
    Breakfast
Stellenbosch below its mountain

Where you stay

  • Cape Town (1 night) City Lodge V&A Waterfront
  • Stellenbosch (1 night) Stellenbosch Hotel
  • Montagu (1 night) Montagu Hotel
  • Karoo (1 night) Karoo Art Hotel
  • Swellendam (1 night) Aanhuizen Guest House
  • Arniston (1 night) Arniston Manor House
  • Hermanus (2 nights) Windsor Hotel
  • Gordon's Bay (2 nights) Quayside Hotel
  • Cape Town (1 night) City Lodge V&A Waterfront

Hotel names are indicative and may be replaced with a property of similar standard and location.

What's included

Included

  • Accommodation 11 nights in hotels, guesthouses and lodges
  • Meals 11 breakfasts and 1 dinner
  • Bike hire and a support vehicle
  • Guided rides throughout
  • Cape Point and the Boulders penguin colony
  • Free day in Hermanus
  • Tour leader throughout

Not included

  • Flights
  • Meals not included 10 lunches and 10 dinners
  • Optional whale-watching trips
  • Travel insurance and personal spending
Rocky shores at Cape Agulhas

This trip might not be for you if…

Honest disclaimer — please read

  • You are new to cycling
  • You want a safari
  • You want most meals included
  • You want flights included — they are not

Good to know

Meals by day Breakfast: Days 2–12 · Lunch: none included · Dinner: Day 1
A mountain road in the Western Cape

In pictures

Departures & prices

From £2,329 per person, twin share, tour only. 7 upcoming departures. Single travellers from £2,865 (single supplement from £536).

Offer Reduced prices on selected dates, shown with the regular price crossed out. Book by 16 Oct.

Frequently asked questions

How do I book this tour?

Tap any "Enquire" button on the page and one of our travel specialists will be in touch within 24 hours (often same day). We'll confirm availability on your preferred date, run through anything you need to know, and only ask for the deposit once you've decided.

What financial protection do I get?

Every Travelisto booking is 100% financially protected. Your money is held in a ring-fenced Trust account until you return from your trip, and we are members of the Protected Trust Services scheme (PTS 6035). Most tours also include ATOL protection where flights are part of the package.

Do I need a visa for South Africa?

No, UK citizens can visit South Africa visa-free for up to 90 days. Your passport needs two blank pages.

How hard is the cycling?

Moderate daily rides on mostly paved roads, with some significant climbs.

Is there a support vehicle?

Yes, it accompanies the group every riding day.

Can I see whales?

From July to November, whales are often seen from the shore at Hermanus.

Can I have my own room?

A single supplement is available on request.

How many people travel together?

Between four and fourteen travellers, with a tour leader.

Can you tailor the trip?

Yes — every escorted tour can be modified into a private tailor-made version with your own dates, adjusted pace, upgraded hotels and add-on extensions. Tell us what you'd like changed when you enquire and we'll quote it both ways so you can compare.

What if my flight is delayed or cancelled?

If your international flight is part of your booking through us, we re-book at no cost. If you've booked flights separately, the tour's local team holds your transfer slot until you arrive. We strongly recommend a comprehensive travel insurance policy that includes delay and cancellation cover.

ATOL protected 100% financially protected in a Trust bank account PTS 6035 4.7 on Trustpilot
Tailor-made option

Not quite the right fit? Make it tailor-made.

If this group tour doesn't match your ideal trip, our specialists will turn it into a private tailor-made journey — your own dates, your own pace, upgraded hotels where you want them, and the parts you don't love swapped out. Same destinations, just rebuilt around you.

Contact us for a tailor-made version of this itinerary
From £2,329
See dates & prices