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Cycling the Cape & Winelands route map

Begin your adventure in cosmopolitan Cape Town, undeniably beautiful, culturally rich and a gateway to the Cape and Winelands. If you arrive in good time we recommend 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 can also be done on Day 12, depending on the weather on Table Mountain).

Around 6pm, say howzit to your tour leader and fellow travellers, when we gather as a group for the first time to get to know each other and learn more about the adventures ahead.

Your tour leader then ensures a big South African welcome by arranging a group dinner.

Want to explore Cape Town further? Secure pre-tour hotel nights through your sales representative.

Meals: Dinner

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 continue cycling to Melkbosstrand, followed by 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.

Meals: Breakfast

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 the T junction, and do a short transfer to Villiersdorp. After lunch, we cycle towards Nuy Valley and then take a short transfer to Montagu.

Meals: Breakfast

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.

Meals: Breakfast

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, with a short transfer, 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.

Meals: Breakfast

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.

Meals: Breakfast

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.

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

Meals: Breakfast

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.

Today you’ll have the chance to join an optional wine tasting just outside of Hermanus.

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

Meals: Breakfast

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.

We pause at Bettie’s Bay, where you have the option to visit a resident penguin colony. This offers a quieter and more intimate wildlife experience than other penguin colonies.

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.

Meals: Breakfast

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.

Meals: Breakfast

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.

There is a 10km stretch along Chapman’s Peak where the support vehicle cannot accompany the group. We rejoin the vehicle in Hout Bay at the end of this section.

Meals: Breakfast

Our adventure ends in Cape Town after breakfast. If you have free time before your flight home you may want to discover more of the waterfront or take a half-day trip to Robben Island.

Alternatively, if you’d like to stay in South Africa longer, speak to your sales representative to discuss our large range of extension options.

Meals: Breakfast

What’s included

All breakfasts and one dinner included across the 12-day itinerary.
11 nights of accommodation: 3 Superior nights and 8 Classic nights in hotels/guesthouses/lodges.
Support vehicle on the rides (nine cycling days with 98% vehicle support; exception is a 10km section on Chapman’s Peak).
Fully serviced Giant Escape 2 Disc touring/hybrid bike hire.
Expert local tour leader plus dedicated support vehicle driver.
All transport for the itinerary, including an airport arrival transfer for any flight and a group departure transfer (subject to the selected group flight).
Immersive itinerary with listed activities, including the walk from the Cape of Good Hope to the old lighthouse at Cape Point and scenic coastal cycling sections such as Chapman’s Peak/Cape Argus route.

What’s not included

International flights to/from Cape Town are not included (land-only pricing shown as excl. flights).
Travel insurance is not included and must be arranged by the traveller.
Visas and vaccinations (where required) are the traveller’s responsibility.
Meals not specified: lunches and all dinners except one are at your own expense.
E-bike upgrade available at an additional cost.
Single room supplement available on request for an additional cost.
Optional activities and entrance fees not listed as included (e.g., penguin colony visit at Boulders Beach, wine tasting in<br/>ear Hermanus).
Room upgrades, such as sea-view rooms in Hermanus, are available at additional cost.

Additional information

For breakfast, expect continental buffets with fresh fruit, cereals, bread, yogurts and tea and coffee. Lunches can consist of a good spread of fresh salads, cold meats, cheese, bread, condiments, fresh fruit and a selection of cold drinks. For evening meals, expect a large braai (barbecue) with lots of locally sourced steaks, sausages and vegetables. Restaurant menus are very varied and our guide will be available to recommend the best options for your personal tastes and budget. You can expect stews, pasta, curry and steaks.

Vegetarians and vegans can be well catered for on this holiday – please inform us before departure of any special dietary requests so our local team can be well prepared.

Drinking water: While the tap water in South Africa is generally considered safe to drink, we recommend avoiding drinking directly from the taps during your stay. Standards and sensitivities can vary, and we want to make sure you stay well throughout your trip. For your comfort and peace of mind, we recommend using filtered or bottled water instead. The water we provide on our vehicles are either from water outlet shops or they’ve been treated with water purification tablets.

Explore Bontebok National Park, a pocket reserve created to save its namesake antelope from extinction. Drive in and wander short riverside paths to spot rare bontebok, mountain zebra and prolific birdlife along the Breede River, with the Langeberg peaks beyond and self-guided nature trails under open skies.

Established in 1931, the park protects threatened renosterveld and fynbos habitats. Keep an eye out for South Africa’s graceful blue crane, kingfishers and sun-loving reptiles warming on rocks.

Cycle the Atlantic seaboard to the kite-surfer beaches north of the city, reaching Bloubergstrand for the classic postcard view of the Table Mountain backdrop. Follow smooth coastal tarmac with sea spray in the air and Robben Island on the horizon, and pause for photos and reflection on this blue-water stretch.

These shoreline suburbs reveal Cape Town’s beach culture and brisk Cape winds, with cafés and surf shacks lining the way. The panorama across Table Bay sets the scene for your Cape riding adventure.

Ride the vine-lined ascent of the historic Hellshoogte Pass into the oak-shaded streets of Stellenbosch. Sweeping views to the Simonsberg and Jonkershoek ranges accompany you before rolling between white-gabled farms and cellar doors, where Cape Dutch architecture meets modern wine country style.

Once a wagon route linking valleys, Hellshoogte rewards with granite peaks, protea-clad slopes and glimpses of storied estates such as Boschendal and Tokara. Expect smooth roads, gentle gradients and a heady sense of place.

Tackle the sinuous switchbacks of the Franschhoek Pass, climbing from the Huguenot village of Franschhoek to a high vantage above vineyards and dams. The road hangs dramatically on the mountain flank, opening to wide skies and exhilarating descents.

French refugees settled these valleys in the 17th century, bringing viticulture and a culinary identity that endures today. From the crest, gaze over the Wemmershoek catchment and fynbos slopes alive with sunbirds and proteas in season.

Pedal quiet backroads through the Little Karoo’s semi-arid valleys, where aloes and succulents stud red-earth plains. Roll into Barrydale for a hosted visit at the Barrydale Co-op Cellar to learn about small-scale production and sample regional chardonnay and other local styles.

This frontier landscape sits between the Langeberg and Tradouws plateaus, with clear air, old trading villages and roadside farm stalls. The co-op model sustains growers across the Overberg, offering an authentic taste of place.

Visit Cape Agulhas, the southernmost point in Africa, where the Atlantic and Indian oceans meet. Stroll the rugged shoreline to the geographic marker and the striking Agulhas Lighthouse, feeling the wind and hearing surf crash against rock-strewn reefs.

This wave-washed coast has claimed many ships; exhibits at the lighthouse recount tales of sailors and currents. Boardwalks protect fragile dunes as cormorants and terns sweep over the headland.

Ride through the palm-lined streets of Elim, a historic Moravian mission village, across rolling wheatlands to the coast. Pause in Stanford to tour and taste at Birkenhead Brewery, before finishing in Hermanus on the cliff-edged shores of Walker Bay.

Founded in 1824, Elim preserves whitewashed cottages and communal gardens. The Overberg’s craft-beer scene complements its farms and fisheries, while Hermanus is famed for shore-based views of southern right whales from June to November.

Ride the Whale Coast via the dramatic Clarence Drive, a cliff-hugging road with vast False Bay panoramas. Sweep past fishing hamlets and kelp-fringed coves beneath the crags of the Kogelberg Biosphere Reserve, with the scent of sea spray and fynbos on the wind.

This UNESCO-designated biosphere hosts the richest floral diversity on earth for its size. Keep watch for Cape baboons on the slopes and surfers carving the breaks below.

Walk the headland from the Cape of Good Hope to the old lighthouse at Cape Point, then cycle through the Cape Point Nature Reserve and along the coast toward Simon’s Town. Expect sweeping ocean vistas, salt-scarred cliffs and endless fynbos.

Part of Table Mountain National Park, this reserve shelters ostrich, eland and bontebok amid endemic flora. The roller-coaster coastal road reveals False Bay in cinematic frames as you freewheel toward naval heritage.

Ride the iconic Chapman’s Peak Drive, chiselled into near-vertical sandstone above the Atlantic. Continue past Hout Bay to Camps Bay and the Twelve Apostles, tracing a leg of the famed Cape Town Cycle Tour route on one of South Africa’s most photogenic stretches.

Engineers opened “Chappies” in 1922, creating a masterpiece of coastal road-building with tunnels and lookouts. Expect azure water, ochre cliffs and frequent stops for photos.

Ascend the Table Mountain Aerial Cableway for a slow-turning ride to the sandstone plateau and far-reaching views over Table Bay and the Twelve Apostles. Wander well-marked pathways through endemic fynbos and photograph the city bowl from above. This experience is at additional cost and bookable on tour.

Part of the Cape Floral Region World Heritage Site, the summit hosts rock hyrax, sunbirds and centuries-old rock formations. Weather can affect operations; your Tour Leader can advise on the best window.

Sail across Table Bay to Robben Island, touring the prison complex with guides who share lived experience. Step quietly into Nelson Mandela’s cell and reflect on South Africa’s journey at this UNESCO World Heritage Site. This experience is at additional cost and bookable on tour.

The ferry approach frames Cape Town against Table Mountain, a striking counterpoint to the island’s austere past. Museum capacity is limited; your Tour Leader can assist with arrangements.

Wander Kirstenbosch National Botanical Garden at the foot of Table Mountain, exploring themed fynbos beds and the sinuous Boomslang Canopy Walkway high in the treetops. Seasonal blooms and sculpture lend texture to this serene green space. This experience is at additional cost and bookable on tour.

Founded in 1913 to preserve indigenous flora, Kirstenbosch is celebrated for showcasing the Cape Floristic Region. Bring a camera for mountain backdrops and jewel-toned sunbirds.

Taste cool-climate wines in the Hemel-en-Aarde Valley just inland from Hermanus, visiting cellar doors renowned for elegant pinot noir and chardonnay. Learn about ocean breezes, clay-rich soils and hands-off winemaking from local hosts. This experience is at additional cost and bookable on tour.

Meaning “Heaven and Earth,” the valley’s rolling vineyards meet fynbos-clad ridges and sea mist drifting up from Walker Bay, a distinctive terroir you can taste in the glass.

Visit an African penguin colony either at Stony Point Nature Reserve, Betty’s Bay or along the Boulders Beach boardwalks near Simon’s Town. Watch birds preen, nest and waddle between boulders at arm’s-length viewing platforms. This experience is at additional cost and bookable on tour.

Once in decline, the species benefits from protected rookeries and careful boardwalk design that keeps human impact low. Expect salty air, braying calls and superb coastal scenery.

Meet your Tour Director and fellow travellers over a convivial welcome dinner at the lively V&A Waterfront. Settle in as you meet your Tour Director and hear about the week’s rides while you sample South African flavours paired with regional wines. Views of Table Mountain and the working harbour frame a relaxed first evening.

Soak up Cape Town’s maritime heritage, where historic warehouses, quays and public art create a characterful dining scene. Expect Cape Malay spice, Karoo produce and ocean-fresh seafood for an inviting warm Cape Town welcome before the cycling begins.

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