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Cycling the Cape & Winelands

Cycling the Cape & Winelands


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  • Holiday type
    Guided cycling
  • Duration
    11 nights
  • Accommodation
  • Activity level
  • From $2079per person, tour only
  • NEW FOR 2019  
  • Departures
    Selected Saturdays if flight incl./Sundays for Tour Only from 22 Sep '19 to 19 Dec '20
  • What your holiday price includes
  • 11 nights hotel-to-hotel accommodation in a mix of hotels
  • All breakfasts, 7 lunches, 2 evening meals
  • Management by our sister company, Exodus
  • Tour leader thoughout
  • High quality bikes provided
  • Full vehicle support
  • All transport and listed activities
  • Tour leader throughout
  • Optional Upgrades
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, bird spotting opportunities, art & history, solo travellers, couples, coastal routes

South Africa

Cycling the Cape & Winelands

  • Discover Cape Town and Table Mountain
  • Try regional produce from the vineyards of Stellenbosch and Franschhoek
  • Visit Cape Algulhas - the southernmost point of Africa
  • 9 days cycling with full vehicle support
  • 95% tarmac, 5% hard pack dirt roads

Renowned as one of the most beautiful places on earth, Cape Town and its surroundings provide a stunning backdrop for this tour. Explore the delights and variety that Cape Town has to offer. Depending on the weather at the top, you could take a cable car ride up Table Mountain for stunning views, visit botanical gardens, or take a trip to Robben Island, the prison where Nelson Mandela and others of the ANC served their long sentences.

Our unique circular route allows us to take in the fantastic sights the Cape Peninsula has to offer. In addition to the opportunity to sample the world-famous wines from the estates of Franschhoek and Stellenbosch, the wild coastline and rugged interior provide classic riding on peaceful roads with little traffic. The stunning scenery, a rich cultural history, unique flora, and unusual wildlife encounters make this a fantastic destination to discover on two wheels.

The best time to see the carpets of wild flowers and fruit blossoms is in the spring (August and September). In the summer months the south easterly wind can blow up to 70km/h at least a few times a month. This helps to cool things off, but can be a little tiring if cycling into it. Our programme is flexible enough to accommodate any major changes in weather, and yet still be enjoyable. February is the hottest month in Cape Town with an average temperature of 23°C. June is the coldest month of the year with an average temperature of 13°C so we avoid running trips at this time. At the times we run most of our trips you can expect warm days with the temperatures around 20°C.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Typical holiday itinerary

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1: Leave London

Take an overnight flight from London to Cape town.

Day 2: Arrive Cape Town; free day to explore

Arrive Cape Town; the day is free for relaxing, shopping, catching a few rays of sunshine or exploring the endless activities in and around the city. Your guide will be on hand to advise and assist, but here are a few recommended options: a cable car ride up Table Mountain for the fantastic view over Cape Town and the coastal regions; a visit to the world famous Kirstenbosch Botanical Gardens or a half-day trip to the infamous Robben Island, the prison where Nelson Mandela and other members of the ANC served their long sentences (this trip can be done on day 13 depending on the weather on Table Mountain).

Day 3: Ride over Hellshoogte, passing vineyards; to Rosenview 50km/31mi

This morning we have a very short transfer from our lodge before an orientation tour through the city bowl and then on to Bloubergstrand - it's from here that the iconic pictures of Cape Town with the backdrop of Table Mountain are taken. After taking the obligatory photos, we're off on 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 famous Boschendal vineyards where we stop for a well-earned drink (optional) before transferring to our accommodation at the Rosenview winery in Stellenbosch.

Day 4: Ride the Franschhoek Pass; afternoon wine tasting in Stellenbosch 20km/12mi

In the morning we have a short transfer before cycling through Franschhoek and up the Franschhoek Pass (739m) for some of the most breathtaking views of this region, before enjoying a fast descent back into town. French Huguenot refugees under the patronage of the Dutch originally settled the town, and their descendants still maintain an excellent museum, tracing their history back to their expulsion from France in 1685. After a full cooked brunch we head out to Stellenbosch, the second oldest town in South Africa, where we have the option to sample some of the finest wines that its 29 cellars have to offer. We use the minibus to travel to the different wine farms in this region.

Day 5: Transfer through Breede Valley; ride through semi-arid desert of Great Karoo 65km/37mi

Today we head east, transferring (140km) through the fertile Breede River valley, passing old settlements verdant with vines and fruit trees and seasonal blossoms. We transfer into Montague and after a short coffee break at a local Route 62 shop, we get onto the bikes for the rest of the day. From here 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 Bushman cultures. We cycle a scenic back road 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 wild flowers (in season). Time allowing we will visit a local co-op cellar and have an opportunity to taste their produce, including the local Chardonnay which is well respected for its unique taste.

Day 6: Ride through Langeberge Mountains to Bontebok N.P.45km/28mi

After breakfast a short climb takes us up and over the spectacular Tradouws Pass. Near the top of the pass is 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 Langeberge 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. This park boasts some rare antelope as well as mountain zebra and some endangered crane species. The park has two 2km self guided nature trails, which can be explored independently.

Day 7: Ride and transfer to Cape Agulhas N.P., Africa's southernmost point 60km/37mi

A short transfer (40km) brings us into the Overburg district, and we cycle through the cultivated farmlands of the Western Cape. 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 of Africa, and South Africa's newest national park, encompassing a large area of wetlands and coastline and extending some kilometres out to the sea. Whales and other sea life that frequent the warm waters of the Indian Ocean enjoy the protection within its boundaries. It also provides a home to thousands of sea birds and seals that can be seen along the rugged beaches. We cycle from Bredarsdorp to Arniston, our overnight spot and weather permitting we spend some time on the beach.

Day 8: Cycle to Hermanus; sample the local fish cakes and beer 55km/34mi

This morning we cycle from Bredarsdorp to the town of Napier. After a short stop and a chance to sample the local fish cakes, we transfer to the Akkedisberg Pass and from here we cycle the very scenic mountain pass into Standford. After a visit to the Birkenhead brewery, with a chance to sample the local beer, we transfer to 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 July through to December, it's a great place to relax. In the afternoon we cycle from one of the local viewpoints of Walkersbay along the Hermanus coastal road to our accommodation offering the best chance to spot whales, in season.

Day 9: Free day to relax in Hermanus

We have a free day today to rest our legs in Hermanus. In the 1920's the town was known as a place to convalesce and was being recommended from as far a field as London. Grand hotels were built and its reputation as a holiday resort was established. Nowadays 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 twelve best places in the world for whale watching.

Join us on our September to October departures for the best chance to see whales swimming off the coast.

Day 10: Ride the Whale Coast to Gordon's Bay 90km/55mi

Today we cycle the Whale Coast, from Hermaus to Gordon's Bay, possible 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 that our efforts will be encouraged by the 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 day. We transfer at the end of the day from Gordon's Bay to Simonstown.

Day 11: Stunning Cape Peninsula ride; visit penguin colony 35km/21mi

After breakfast, a short 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.

Day 12: Cycle to Cape Town via Chapman's Peak, Hout Bay and Camps Bay 70km/43mi

The ride today follows part of the annual Cape Argus route, one of the largest cycling events of the world, and is arguably the most scenic route that South Africa has to offer. We complete our circuit by cycling from Glencairn over the redhill pass along an old navy road to Scarborough and then all 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 on to 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.

Day 13: 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 the half-day trip to Robben Island before the trip ends here.

Day 14: Arrive London

Land in London where the trip ends.

Cycling Conditions

This tour is classified: Road Activity level 3 (Moderate) 10 days cycling with an average distance of approximately 55km (34 miles) per day with full vehicle support. A classic road tour with relaxed rides and the opportunity for a few challenging climbs. Mainly good quality tarmac with a few excursions onto hard-packed graded roads. This trip uses main roads which can be busy, but the scenery from the route we take is wonderful. All of the roads used are of good quality tarmac except the occasional stretch of dirt road in the wine district and at Cape Agulhas.

Legal Note: all group members joining this tour will be asked to sign an indemnity form at the start of the holiday. This indemnity form is a requirement of the South African Tourism Service Association which our local supplier is a member of. As a client of Exodus Travels Ltd, your rights under the Package Travel Regulations (1992) are unaffected, and Exodus remains liable for the actions of our sub-contractors.


South Aftica

All nationalities require a full passport that must be valid for 6 months beyond the intended length of stay. It is your responsibility to have the correct personal documents and to obtain your own visa, if one is necessary, in accordance with the regulations of the country you are to visit. The information offered below is to help you with that process. We are not responsible for the actions of local immigration and customs officials, whether at points of entry or otherwise, and any subsequent effects.


South Aftica

British passport holders and most European and Commonwealth Passport holders do not require a visa to travel to South Africa. Please note that all travellers to South Africa who do require a visa are required to have a minimum of 2 blank consecutive pages in their passport i.e. a left hand page and a right hand page to enable an entry visa to be issued.

Please note that new regulations from the 1 June 2015 mean that any child under 18 travelling to South Africa needs to be in possession of an unabridged birth certificate with the names of both parents. If a child under 18 is only travelling with a single parent, they will also have to have an affidavit, no less than 3 months old, from the absent parent confirming the child can travel with the other parent; a court order granting full legal guardianship of the child; or a death certificate of the deceased parent.

Visa regulations can change without notice: please check the current regulations in good time to obtain a visa if one is required.


South Africa

No vaccinations are obligatory but some vaccinations are recommended. These include typhoid, yellow fever,hepatitis A, hepatitis B, rabies, measles, mumps and rubella (MMR) andinfluenza. Travel health can often be something people forget about before going away, but a little preparation and knowledge can go a long way to help you stay fit and healthy while abroad.

We are advised that there is no risk of malaria on this trip. Bilharzia is known to occur in some of the lakes or rivers visited on this itinerary, we therefore advise all to take advice from your guide or leader locally before venturing for a swim.

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Lodges and Chalets, South Africa

Throughout the trip we stay in locally run lodges and chalets with plenty of individual character. The majority of these are small, privately owned establishments and all are clean and comfortable. We have chosen a range of properties, most specifically for their excellent locations; in Cape Town we stay in Seapoint, near the Waterfront which is a very popular and central area, in Hermanus we are close to the sea and in Stellenbosch we stay at the Rosenview wine farm where we can sample the locally made wines. All accommodation has en suite facilities and are of a high standard throughout the tour.

7 nights guest houses and 4 nights lodges, all en suite

Eating & Drinking

All breakfasts, 7 lunches and 2 dinners are included. For breakfast you can expect a continental style buffet with fresh fruit, cereals, bread, yogurts and tea and Coffee. On some days our guides will prepare a cooked breakfast when they have the facilities to do so. For lunches that are included in the trip you can expect a good spread of fresh salads, cold meats, cheese, bread, condiments, fresh fruit and a selection of cold drinks. For evening meals that are included in the trip you can expect a large Braai (BBQ) with lots of locally sourced steaks, sausages and vegetables. Restaurant menus are very varied and our guide will be on hand to recommend the best options for your personal tastes and budget. You can expect stews, pasta, curry and steaks. Vegetarians are easily catered for.


Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.


Here at Headwater we thrive on feedback from our customers. It's the only way we can continue to develop, and where necessary improve, our services and ensure our holidays continue to be the best they can be. However, as this is a relatively new holiday, we don't yet have any customer reviews available.

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

This 11 night guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of hotels

All breakfasts, 7 lunches, 2 evening meals

Management by our sister company, Exodus

Tour leader thoughout

High quality bikes provided

Full vehicle support

All transport and listed activities

Tour leader throughout

How to book:

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

  • Sep
  • Oct
  • Nov
  • Dec
  • Jan
  • Feb
  • Apr
  • Sep
  • Oct
  • Nov
  • Dec
Sep 2019Tour only Availability
22nd Sep US$2079 Check availability
Oct 2019Tour only Availability
6th Oct US$2079 Check availability
Nov 2019Tour only Availability
3rd Nov US$2079 Check availability
17th Nov US$2129 Check availability
Dec 2019Tour only Availability
1st Dec US$2079 Check availability
22nd Dec US$2079 Check availability
Jan 2020Tour only Availability
5th Jan US$2099 Check availability
Feb 2020Tour only Availability
2nd Feb US$2099 Check availability
16th Feb US$2099 Check availability
Apr 2020Tour only Availability
12th Apr US$2099 Check availability
Sep 2020Tour only Availability
6th Sep US$2099 Check availability
20th Sep US$2099 Check availability
Oct 2020Tour only Availability
4th Oct US$2099 Check availability
18th Oct US$2099 Check availability
Nov 2020Tour only Availability
1st Nov US$2099 Check availability
15th Nov US$2099 Check availability
29th Nov US$2099 Check availability
Dec 2020Tour only Availability
19th Dec US$2099 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Minimum group sizes
A minimum of 5 people (in total) are required for each departure.

This holiday is unsuitable for children.

Holiday type
Guided cycling Managed by our sister company, Exodus.

Selected Saturdays if flight incl./Sundays for Tour Only from 22nd Sep 2019 to 19th Dec 2020, for 11 nights. All dates are subject to availability, please contact us to check.

All breakfasts, 7 lunches, 2 evening meals

Other details
Join us on our September to October departures for the best chance to see whales swimming off the coast. Tour Only arrivals are Sundays

Tailor-made travel

If you choose to book your own flights please check with us first that your chosen departure date is definitely operating as our guided holidays are subject to minimum group sizes.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.

Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Cycling the Cape & Winelands. Simply complete the form below (fields marked * are mandatory) and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.

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