Cycling the Cape & Winelands

We 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).

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

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

Today we head east, cycling from our accommodation in Montagu to our 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. We cycle a scenic backroad traversing a more fertile region known as the Little Karoo, a short climb brings us to the Tradouws Plateau before arriving in Barrydale, our 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, we visit a local co-op cellar and have an opportunity to taste their produce, including the well-respected local chardonnay.

After breakfast, a short climb takes us up and over the spectacular Tradouws Pass. Near the top are the remains of a prison camp once home to the convicts that 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, we reach our base for the night, Swellendam. From here, we 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.

A short transfer (12mi/20km) brings us into the Overberg district, and we 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.

This morning, we cycle through the picturesque hamlet of Elim and past 34mi (55km) of undulating farmlands to the coastal town of Kleinbaai. Following lunch, we take a short transfer into Stanford where we can sample local beer at the Birkenhead Brewery. We finish our 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, we 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.

Accommodation: Windsor Hotel (or similar)

Upgrade to a sea-view room today – speak to your sales representative for more details

We have a free day today to rest our 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 recognises Hermanus as among the best places in the world for whale watching.

Our September to October departures give the best opportunity to see whales swimming off the coast.

Accommodation: Windsor Hotel (or similar)

Upgrade to a sea-view room today – speak to your sales representative for more details

Today we cycle the Whale Coast, from Hermaus 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 our 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. We transfer at the end of the day from Gordon's Bay to Simonstown.

After breakfast, an 18mi (30km) transfer brings us to the Cape Point Nature Reserve. We then walk from the Cape of Good Hope to the old lighthouse at Cape Point. From here, we 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, we visit the local penguin colony (optional). We then continue our cycle along the coastal road to our overnight accommodation.

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. We complete our circuit by cycling from Glencairn over the Red Hill pass 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, we cycle up Suikerbos Ridge past Llandudno and then onto Cape Town via Camp's Bay and the 12 Apostles all the way to our accommodation in Seapoint. We celebrate the end of the cycling at one of the many venues at the Waterfront.

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.