Cycling the Cape and Winelands

Itinerary Details

1. Day 1Start Cape Town; free day to explore

   Arrive in Cape Town. The day is free to relax, shop, catch a few rays or explore the endless activities in and around the city. The guide can advise and assist, but here are a few recommended options: a cable car ride up Table Mountain for fantastic views over Cape Town and the coast; a visit to the Kirstenbosch Botanical Gardens; or a half-day trip to Robben Island, where Nelson Mandela and other members of the ANC served long prison sentences (this trip can be done on Day 12, depending on the weather on Table Mountain).
   
   

   • City Lodge Hotel Victoria & Alfred Waterfront (or similar)
2. Day 2Ride over Hellshoogte, passing vineyards; to Stellenbosch

   This morning, you'll have a short transfer from your lodge to the harbor and then cycle to Bloubergstrand, where the iconic pictures of Cape Town with Table Mountain as a backdrop are taken. After taking the obligatory photos, you'll have a short transfer into the center of the winelands. In the afternoon, you'll cycle over Hellshoogte (Hell’s Heights) and then freewheel the rest of the way to the Boschendal vineyards where you'll stop for a well-earned drink (optional) before transferring to the accommodation in Stellenbosch.
   
   
   
   

   • 23.6 miles
   • 259.2 ft
     1,095.8 ft
     836.6 ft
   • San Gabriel Homestead (or similar)
   • Breakfast

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     San Gabriel Homestead

     Another quality accommodation choice used on the trip

3. Day 3Ride the Franschhoek Pass

   In the morning, you'll have a short transfer before cycling through Franschhoek and up the Franschhoek Pass (2,425ft/739m) for some of the most breathtaking views in the region. You'll then continue to cycle to Villiersdorp. After lunch, you'll cycle towards Nuy Valley and then take a short transfer to Montagu.
   
   
   

   • 43.5 miles
   • -52.5 ft
     3,277.6 ft
     3,330.1 ft
   • Montagu Hotel (or similar)
   • Breakfast

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     Montagu: Montagu Hotel

     The Montagu Hotel is an architectural gem that opened in 1875. It was refurbished with original art deco and Victorian furniture and has two swimming pools, two restaurants, a spa and garden

4. Day 4Ride through the semi-arid desert of Great Karoo

   Today you'll head east, cycling from your accommodation in Montagu to your accommodation in Barrydale. Along the way, the landscape changes to the semi-arid desert of the Great Karoo, a huge ancient plateau making up almost a third of South Africa’s landmass and littered with remains of ancient indigenous cultures. You'll cycle a scenic backroad traversing a more fertile region known as the Little Karoo, a short climb brings you to the Tradouws Plateau before arriving in Barrydale, your base for the night. This quiet old Dutch village is in a fertile valley surrounded by a colourful mix of vines, fruits and wildflowers (in season). While here, you'll visit a local co-op cellar and have an opportunity to taste their produce, including the well-respected local chardonnay.
   
   
   
   

   • 39.1 miles
   • 475.7 ft
     2,972.4 ft
     2,496.7 ft
   • Karoo Art Hotel (or similar)
   • Breakfast
5. Day 5Ride through Langeberg Mountains to Bontebok National Park

   After breakfast, a short climb takes you up and over the spectacular Tradouws Pass. Near the top are the remains of a prison camp once home to the convicts who constructed the pass in 1873. From here, the route is mainly downhill through the Langeberg Mountains to the small town of Suurbrak. Built by the London Missionary Society in 1812, many of the buildings have been restored and now the town has the feel of a living museum. Moving on, you'll reach your base for the night, Swellendam. From here, you'll drive to the Bontebok National Park, home to rare antelope, mountain zebras and endangered crane species. The park has two 1.2mi (2km) self-guided nature trails, which can be explored independently.
   

   
   
   
   
   
   

   • 21.1 miles
   • -908.8 ft
     928.5 ft
     1,837.3 ft
   • Aanhuizen Guest House or Aan de Eike Guest House (or similar)
   • Breakfast
6. Day 6Ride and transfer to Cape Agulhas National Park, the southernmost point in Africa

   A short transfer (12mi/20km) brings you into the Overberg district, and you'll cycle through the cultivated farmlands of the Western Cape to Bredasdorp. The road gently rolls through neat wheat fields and remote fishing villages facing the Indian Ocean, arriving at Cape Agulhas. This is the southernmost point in Africa, and the newest national park in the country, encompassing vast wetlands, coastline and extending some kilometres out to sea. Whales and other sea life that frequent the warm Indian Ocean here enjoy the protection. It also provides a home to thousands of sea birds and seals that can be seen along the rugged beaches.
   
   
   
   
   
   

   • 33.6 miles
   • -423.2 ft
     1,876.6 ft
     2,299.9 ft
   • Cape Agulhas Guest House (or similar)
   • Breakfast
7. Day 7Cycle towards Hermanus; sample local beer at Birkenhead

   This morning, you'll cycle through the picturesque hamlet of Elim and past 34mi (55km) of undulating farmlands to the coastal town of Kleinbaai. Following lunch, you'll take a short transfer into Stanford where you can sample local beer at the Birkenhead Brewery. You'll finish your day in the town of Hermanus, famous for the very close sightings of the southern right whale, which come into the secluded bay to mate and calf each year from June to November.

   In the afternoon, you'll have the option of cycling from one of the local viewpoints of Walker Bay along the Hermanus coastal road to our accommodation, offering the best chance of spotting the whales.
   
    
   
    
   
   
   
   
   
   

   • 31.1 miles
   • 85.3 ft
     944.9 ft
     859.6 ft
   • Windsor Hotel (or similar)
   • Breakfast

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     Hermanus: Windsor Hotel

     The 120-year-old Windsor Hotel sits opposite Walker Bay, one of the best whale-watching destinations in the world when southern right whales migrate to the bay to breed (July to November)

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     Hermanus: Windsor Hotel

     The 120-year-old Windsor Hotel sits opposite Walker Bay, one of the best whale-watching destinations in the world when southern right whales migrate to the bay to breed (July to November)

8. Day 8Free day to relax in Hermanus

   You'll have a free day today to rest your legs in Hermanus. In the 1920s, the town was known as a place to convalesce and was being recommended from as far afield as London. Grand hotels were built and its reputation as a holiday resort was established. It still manages a delightful balance between the two industries of fishing and tourism. In addition to this, the World Wildlife Foundation recognizes Hermanus as among the best places in the world for whale watching.
   
   The September to October departures give the best opportunity to see whales swimming off the coast.
   
   
   
   
   
   

   • Windsor Hotel (or similar)
   • Breakfast

   • 

     Hermanus: Windsor Hotel

     The 120-year-old Windsor Hotel sits opposite Walker Bay, one of the best whale-watching destinations in the world when southern right whales migrate to the bay to breed (July to November)

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     Hermanus: Windsor Hotel

     The 120-year-old Windsor Hotel sits opposite Walker Bay, one of the best whale-watching destinations in the world when southern right whales migrate to the bay to breed (July to November)

9. Day 9Ride the Whale Coast to Gordon's Bay

   Today you'll cycle the Whale Coast, from Hermanus to Gordon’s Bay, one of the most scenic rides in the world. The road follows the rugged coastline, passing through fishing villages with dramatic views over False Bay and the Cape of Good Hope. Along the route, there is a good chance your efforts will be encouraged by numerous troops of Cape Baboon. Today is the longest cycle day, but those preferring a shorter ride can catch a lift in the support bus for part of the journey. You'll transfer at the end of the day from Gordon’s Bay to Simonstown.
   
   
   
    
   
   
   
    
   
   

   • 48.5 miles
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     2,178.5 ft
     2,178.5 ft
   • Quayside Hotel (or similar)
   • Breakfast

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     Simonstown: Quayside Hotel

     This bright and breezy boutique hotel is centrally located in Simonstown on the water’s edge. Rooms are outfitted with an elegant nautical design and have lovely views

10. Day 10Cape Peninsula ride; visit penguin colony

    After breakfast, an 18mi (30km) transfer brings you to the Cape Point Nature Reserve. You'll then walk from the Cape of Good Hope to the old lighthouse at Cape Point. From here, you'll cycle through the Cape Point Nature Reserve and then along the very scenic coastal road to the historic village of Simonstown, downhill for most of the way, with panoramic views over False Bay. After a rest stop and lunch at Boulders Beach, you'll visit the local penguin colony (optional). You'll then continue your cycle along the coastal road to your overnight accommodation.
    
    
    
    
    
    
    
    
    

    • 14.3 miles
    • -370.7 ft
      823.5 ft
      1,194.2 ft
    • Quayside Hotel (or similar)
    • Breakfast

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      Simonstown: Quayside Hotel

      This bright and breezy boutique hotel is centrally located in Simonstown on the water’s edge. Rooms are outfitted with an elegant nautical design and have lovely views

11. Day 11Cycle to Cape Town via Chapman's Peak, Hout Bay and Camps Bay

    The ride today follows part of the annual Cape Argus route, one of the largest cycling events in the world, and is arguably the most scenic route in South Africa. You'll complete your circuit by cycling from Glencairn over the Red Hill passing along an old navy road to Scarborough and then along the Atlantic coast via the stunning Chapman’s Peak drive into Hout Bay.

    After lunch in Hout Bay, you'll cycle up Suikerbos Ridge past Llandudno and then onto Cape Town via Camp’s Bay and the 12 Apostles all the way to your accommodation in Seapoint. You'll celebrate the end of the cycling at one of the many venues at the Waterfront.
    
    
    
     
    
    
    
     
    
    

    • 34.2 miles
    • 859.6 ft
      3,461.3 ft
      2,601.7 ft
    • City Lodge Hotel Victoria & Alfred Waterfront (or similar)
    • Breakfast
12. Day 12Optional morning visit to Robben Island; end Cape Town

    The day is free for last-minute shopping, catching a few last rays of sunshine or taking the half-day trip to Robben Island before the trip ends.
    
    
    
    

    • Breakfast