Cycling the Cape & Winelands

4.7Based on

Carbon neutral

12 daysDuration

Small Group TourUsually 8-12 participants, maximum 18 travelers

14 peopleMaximum group size

16 - 99 yearsAge range for participants

EnglishGuide language

Moderate

Involves sustained activity requiring a reasonable level of fitness and endurance.

Starts

Cape Town, South Africa

Ends

Cape Town, South Africa

Highlights

Ride a selection of beautiful South African landscapes: vineyards, mountain passes and coast

Cycle part of the stunning Cape Argus route, one of the largest cycling events in the world

Take the chance to sample exquisite produce from the Stellenbosch vineyards

Visit Cape Agulhas, the southernmost point in Africa

Begin and end in Cape Town with the option of visiting Robben Island, Table Mountain and more

Itinerary

Cycling enthusiasts will find their dream getaway on the "Cycling the Cape & Winelands" tour—a 12-day bicycle adventure that circles out from Cape Town into the heart of South Africa’s most stunning regions. This moderate-activity trip is tailored for experienced travelers eager to immerse themselves in the area’s vibrant scenery, rich heritage, and unique wildlife, all from the saddle.

Pedal along peaceful, low-traffic roads that wind through the iconic Cape Peninsula, where Table Mountain looms over the city and the wild coastline unfurls in dramatic fashion. The route takes you through celebrated wine regions like Stellenbosch and Franschhoek, offering plenty of opportunities to sample local vintages and learn about the region’s deep-rooted viticultural traditions.

Beyond the vineyards, the journey ventures to Cape Agulhas—the continent’s southernmost tip—and traverses the rugged interior, where you’ll encounter distinctive flora and fauna found nowhere else on earth. The ever-changing landscapes, from rolling hills to rocky outcrops and tranquil bays, guarantee every day brings a fresh sense of adventure.

The unique selling point? This tour package combines classic rides, world-famous sights, and off-the-beaten-path discoveries, making it the ultimate way to experience the Cape’s diversity. With expert guides, comfortable accommodations, and small group camaraderie, you’ll enjoy the perfect balance of challenge, exploration, and relaxation in one unforgettable cycling trip.

day 1 - Start Cape Town; free day to explore

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).

Accommodation:City Lodge Hotel Victoria & Alfred Waterfront (or similar)

day 2 - Ride over Hellshoogte, passing vineyards; to Stellenbosch

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.

Meals:Breakfast

Others:San Gabriel Homestead (or similar)

day 3 - Ride the Franschhoek Pass

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.

Meals:Breakfast

Accommodation:Montagu Hotel (or similar)

day 4 - Ride through the semi-arid desert of Great Karoo

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

Accommodation:Karoo Art Hotel (or similar)

day 5 - Ride through Langeberg Mountains to Bontebok National Park

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.

Meals:Breakfast

Others:Aanhuizen Guest House or Aan de Eike Guest House (or similar)

day 6 - Ride and transfer to Cape Agulhas National Park, the southernmost point in Africa

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

Others:Cape Agulhas Guest House (or similar)

day 7 - Cycle towards Hermanus; sample local beer at Birkenhead

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

Meals:Breakfast

Accommodation:Windsor Hotel (or similar)

day 8 - Free day to relax in Hermanus

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

Meals:Breakfast

Accommodation:Windsor Hotel (or similar)

day 9 - Ride the Whale Coast to Gordon's Bay

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.

Meals:Breakfast

Accommodation:Quayside Hotel (or similar)

day 10 - Cape Peninsula ride; visit penguin colony

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

Accommodation:Quayside Hotel (or similar)

day 11 - Cycle 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. 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.

Meals:Breakfast

Accommodation:City Lodge Hotel Victoria & Alfred Waterfront (or similar)

day 12 - Optional 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.

Meals:Breakfast

Get Trip Brochure & Exclusive Discount

Download a detailed PDF brochure and unlock an exclusive discount for this tour

What's Included

Accommodation

All accommodation

Meals

All breakfasts

Transport

All transport and listed activitiesArrival transfer for any flight, group departure transfer available

Guide

Tour leader throughout

Others

Local bike hire

What's Excluded

Customer Reviews

Read what other travelers have to say about Cycling the Cape & Winelands

4.7

based on 79 reviews

Tour Availability

Select your preferred departure date and secure your spot

Christmas Super Sales Extended SalesUp to 10% off

Loading availability...

Monthly Price Comparison

Good to Know

Cancellation

Payment

Travel Insurance

Visa

Do you need help from our trip consultants?

If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us.

Our travel experts are ready to help.

Why Book with Bookmundi

Earn USD 129+ in travel credits.

Best price guaranteed.

No credit card or booking fees.

100% financial protection.Bookmundi is a member of the Danish Travel Fund which guarantees for any payment made via us. Our guarantee covers all travelers, irrespective of nationality.

Carbon neutral tours.Algorithms and machine learning enables Bookmundi to calculate the carbon footprint for each tour. We then subsequently offset carbon emissions for all tour bookings on Bookmundi via investments in carbon reduction projects to help combat climate change.

25,000+ trip reviews, with an average rating of 4.8 out of 5.

What are customers saying about Bookmundi

4.67/5

Excellent based on 808 customer reviews from

Anonymous

Sistema di prenotazione semplice e intuibile. In caso di necessità le istruzioni presenti sul sito sono risultate utili e chiare. Nessun problema riscontrato

1 week ago

Similar Tours You Might Like

Discover our top tours similar to Cycling the Cape & Winelands that you might like.

Cape Town & the Garden Route

4.9(89 reviews)

The legendary Garden Route comes alive on "Cape Town & the Garden Route," a 12-day food-focused journey perfect for senior travelers seeking iconic South African experiences. Beginning in Port Elizabeth and winding toward cosmopolitan Cape Town, this relaxed tour features a safari in Addo Elephant National Park, enchanting cellar tours in Stellenbosch, and a close-up look at Simon’s Town’s playful penguins. Ample free time in Cape Town lets you soak in its rich atmosphere. Travel between June and November for a chance to spot migratory southern right whales—a rare natural spectacle. With all logistics handled, this trip’s unique selling point is its blend of culinary delights, wildlife encounters, and scenic wonders, making for a truly memorable South African tour package.

12 days

South Africa Escape

4.7(78 reviews)

From the windswept coast of Cape Town to the untamed wilds of Kruger, "South Africa Escape" is a 14-day wildlife trip designed for experienced travelers and seniors eager to experience the Rainbow Nation’s diversity. Journey along the Atlantic and Indian Oceans, explore charming towns, and marvel at the Garden Route’s spectacular scenery. Traverse the legendary Route 62, experience semi-desert landscapes of the Great Karoo, and seek out iconic wildlife in the Kruger region. With all logistics taken care of, this moderate-activity tour’s unique selling point is its comprehensive coverage of South Africa’s natural and cultural highlights, ensuring a vivid introduction to the country’s vibrant spirit.

14 days

South Africa: Walking & Wildlife

4.8(56 reviews)

South Africa’s call of the wild comes alive on the "Walking & Wildlife" tour, a 15-day adventure designed for seasoned explorers with a passion for nature and discovery. Starting and ending in Johannesburg, this moderate-activity trip leads you through the dramatic Drakensberg mountains, into iconic safari destinations like Kruger National Park, and across the diverse landscapes of Letaba Ranch Reserve, Eswatini, St Lucia, and more. Experience the thrill of walking beneath towering peaks in the Drakensberg—aptly named Dragon Mountain—where every footstep reveals sweeping vistas and untamed beauty. In between invigorating treks, the tour immerses you in the heart of South Africa’s legendary wildlife. Hope to spot the Big Five—elephants, lions, rhinos, leopards, and buffalo—as well as giraffes, cheetahs, and other remarkable species during expertly guided game drives. The journey is enriched with cultural encounters, including visits to Eswatini (Swaziland), the wetlands of St Lucia, and historic battlefields, offering a deep dive into the region’s heritage. Designed for experienced travelers, the itinerary balances active exploration with comfortable accommodations, ensuring you have the energy to fully engage each day. What truly sets this tour apart is its unique combination of guided walks in spectacular wilderness areas and close-up wildlife experiences—giving you a comprehensive, immersive perspective on South Africa’s natural and cultural treasures. This is the trip for those who crave both the freedom of the trail and the excitement of a classic safari, all in one unforgettable package.

15 days

Explore Southern Africa

5.0(1 review)

From the Okavango Delta’s winding waterways to the wildlife-rich national parks of Hwange, Kruger, and Matobo, this 18-day "Explore Southern Africa" trip unveils the region’s wild spirit in grand style. Designed for those drawn to natural wonders and authentic encounters, this moderate-activity road tour leads you through South Africa, Botswana, and Zimbabwe, connecting you with elephants, lions, rhinos, leopards, and more. Canoe past hippos in the Okavango, embark on safaris in legendary reserves, and sleep beneath the southern stars in campsites, bush camps, and even a local village homestay. The adventure is immersive—expect to bond with fellow travelers and locals alike as you swap stories by the fire and awake to the sounds of the African bush. A standout feature of this tour package is the sheer variety of landscapes and habitats you’ll experience, from shimmering deltas to rugged savannas. With all logistics—including accommodation, meals, and expert-guided activities—handled for you, this journey is as seamless as it is unforgettable. If you’re searching for a trip that delivers both iconic wildlife sightings and a true taste of Southern Africa’s diverse beauty, look no further.

18 days

Journeys: Explore Cape Town & Kruger National Park

5.0(12 reviews)

Experience the dramatic contrasts of South Africa on the "Journeys: Explore Cape Town & Kruger National Park" tour, a 10-day odyssey from the vibrant streets of Cape Town to the wildlife-rich plains of Kruger. Begin with the city’s stunning scenery and rich cultural tapestry, then trace history in Johannesburg, once home to Nelson Mandela. The highlight for many is the safari in Kruger National Park—guided by conservationists from National Geographic’s Big Cat Initiative—where you’ll scan the savanna for lions, elephants, and rhinos. Each evening, soak in unforgettable sunsets over the African landscape. With accommodations, transport, and meals included, this trip stands out for its blend of urban culture, historical depth, and iconic wildlife experiences—making it a comprehensive tour package for anyone seeking South Africa’s best.

10 days

Kruger Park Highlights

Unleash your inner adventurer on the "Kruger Park Highlights" tour, a 4-day wildlife safari designed with seniors in mind. Starting and ending in Johannesburg, this self-guided group trip offers a window into South Africa’s untamed beauty and cultural diversity. Track the Big Five and more through the vast, unfenced wilderness of Kruger National Park, one of Africa’s richest wildlife havens. Experience the panoramic splendor of the Blyde River Canyon along the renowned Panorama Route, where dramatic cliffs and lush vistas provide the perfect backdrop for unforgettable memories. With accommodations, meals, and transport all taken care of, this easy-activity tour package is as comfortable as it is exhilarating. The highlight? The chance to witness Africa’s legendary wildlife roaming free, making every game drive a new adventure.

4 days

Cape Town & the Garden Route

4.4(20 reviews)

From the cosmopolitan energy of Cape Town to the lush wilderness of the Garden Route, this nine-day tour package delivers a sophisticated blend of city and nature. Designed for experienced travelers and seniors seeking a moderate level of activity, the journey begins in Cape Town, exploring its vibrant streets before heading through iconic destinations like Knysna, Mossel Bay, and the awe-inspiring Cango Caves. Highlights include scenic drives, engaging city sightseeing, and explorations of South Africa’s famed coastlines. Accommodations in comfortable hotels, group transport, and included meals ensure a seamless travel experience. What sets this trip apart is its perfect balance of urban discovery and natural beauty, offering both cultural immersion and the thrill of South Africa’s landscapes. If you’re looking to experience the best of South Africa’s western treasures without missing a beat, this thoughtfully curated tour is an exceptional choice.

9 days

Keep Exploring South Africa

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

Hi there

Highlights

Itinerary

day 1 - Start Cape Town; free day to explore