A beautiful picture of the Cape Peninsula & Winelands Cycling Holiday tour

Cape Peninsula & Winelands Cycling Holiday

6 Nights

From $2,080 USD

Tour Highlights:

Bainskloof Pass
Stellenbosch via West Coast
Helshoogte Pass

Cape Peninsula & Winelands Cycling Holiday

Journey Overview

Embark on an unforgettable Fair Trade Cycling Adventure, indulging in a thrilling cycling holiday that immerses you in the breathtaking landscapes of the Cape Peninsula & Winelands. Begin your journey with a two-night stay at Parker Cottage, Cape Town, exploring iconic landmarks like Table Mountain and the V&A Waterfront. Guided by Chris Hannival, your cycling escapade kicks off with bike fitting and a scenic ride through Woodstock and the Atlantic Seaboard. Day 3 unfolds with your inaugural cycle tour around the Cape Peninsula, culminating at the Vineyard Hotel in Newlands, spanning 130km of scenic routes.

Venturing onward on Day 4, traverse 75km to Stellenbosch via the picturesque West Coast, relishing a stay at the historic Oude Werf Hotel. Indulge in a delectable lunch at Durbanville Hills Wine Estate. Day 5 promises another delightful 75km ride, ascending the Helshoogte Pass through Pneil, with pit stops at Val de Vie estate and Wellington before reaching the serene Bartholomeusklip Farm. Day 6 presents a scenic cycling odyssey over the Bainskloof Pass, culminating in a lavish lunch at Bersig Estate Bistro and an overnight stay at The Tulbagh Hotel.

Wrap up your adventure on Day 7 with exhilarating off-road cycling at Boschendal Farm, offering routes ranging from easy to extreme. After a rejuvenating lunch and shower, bid farewell to an unforgettable journey, customizable to your preferences with options like e-bikes and varied accommodations. Experience the ultimate cycling holiday amidst South Africa's natural wonders.

Days 1 - 2
Cape Town to Atlantic Seaboard

Energizing Arrival in Cape Town

  • Your Accommodation

    On your first day, relax after your flight and take some time to acclimatise.

    Your home away from home:

    Parker Cottage
    www.parkercottage.co.za
    3 Carstens Street, Tamboerskloof
    Tel +27 21 424 6445

  • Your Travel Time

  • Your Activities

    You'll enjoy the village of Tamboerskloof (where Parker Cottage is situated) for its quiet but central location: take a stroll down to Kloof Street for a coffee and browse in the bookshops and art galleries. There's an opportunity to visit Table Mountain, the V&A Waterfront or the Old Town or perhaps take a paragliding flight from Signal Hill over the Atlantic Ocean.

    On your second day, you’ll be collected from Parker Cottage by Chris Hannival of Hannival’s Tours and taken to iRide Africa in Mowbray for your bike fitting. We’ll then do a short ride back to Parker Cottage stopping off in Woodstock, the Old Town and the Winchester Mansion Hotel for lunch. The afternoon is free in case you’d like to visit Table Mountain or the V&A Waterfront.

  • Your Food
Day 3

Coastal Cycling: Cape to Vineyard

  • Your Accommodation

    Your accommodation for the night is just a little further on at the Vineyard Hotel in Newlands (Constantia). With over 200 years of history within its walls, The Vineyard is situated in six acres of attractive landscaped parkland on the banks of the Liesbeek River. This beautiful building is most unusual for its time in that it was built then a very long way away from Cape Town itself and over two stories in a Regency (rather than a Cape Dutch) style. It was the original home of Lady Anne Barnard but on conversion into a hotel had extensions designed by highly acclaimed architects Jack Barnett and Revel Fox. It is filled with works by leading South African artists and offers rooms ranging from single to family suites, both mountain and courtyard facing.

    The hotel offers its guests two swimming pools - one outdoor, surrounded by loungers and one heated indoor pool. You’ll be pleased to hear that after a long day in the saddle there is a world-class spa on site too.

    Your home away from home:

    The Vineyard Hotel
    www.vineyard.co.za
    Colinton Road, Newlands
    Tel +27 21 657 4500

  • Your Travel Time

    Today's ride is 132 km's.

  • Your Activities

    Today you’ll start your ride from Parker Cottage and head south along the foot of the Twelve Apostles mountain range (the western side of Table Mountain). You’ll ride all the way along the western coastline of the Cape Peninsula, riding up and down the famous Chapman’s Peak Drive and through the seaside villages of Kommetjie and Scarborough. The ride is 132km.

    If there’s time, we’ll take a detour into the Cape Point park and cycle right to the ‘tip of Africa’, before stopping for a well-deserved lunch at The Black Marlin near Simonstown.

  • Your Food

    There are two restaurants with reputations in their own rights at the Vineyard: “the Square”, a great favourite for breakfast and dinner, as well as a popular sushi bar and Myoga Restaurant which offers a modern fusion style of cooking. Myoga is open for lunch and dinner and the Square for breakfast and dinner.

Day 4

From West Coast to Winelands

  • Your Accommodation

    The Oude Werf which is right in the heart of the old centre combines a centuries-old heritage as South Africa’s oldest continuously operating hotel with luxury contemporary comforts and intimate hospitality. Whilst it has over 50 rooms and suites it feels like you’re staying in a much smaller establishment.

    The pool area is particularly interesting being framed on the one side by the newer block of rooms and on the other by the original building.

    Your home away from home:

    Oude Werf Hotel
    www.oudewerf.co.za
    30 Church street, Stellenbosch
    Tel +27 21 887 4608

  • Your Travel Time

    Today's ride is 68km.

  • Your Activities

    Today you’ll take a much shorter ride along the West Coast, which is the coastline that stretches north from Cape Town. You’ll stop off for lunch at the delightful Durbanville Hills Winery, now a major exporter of wine across the planet. After a bit more time in the saddle, we’ll head south again to the historic Winelands ‘capital’ of Stellenbosch which happens to also be a university town. The centre is a maze of beautiful tree-lined streets, cafes, restaurants, antique shops and small owner-managed stores.

  • Your Food

    Enjoy classic Cape flavours and vintages at the superb restaurant (which is interestingly a popular choice with locals, not just residents) and the vine-covered courtyard.

Day 5

Biking to the Countryside

  • Your Accommodation

    After the city stays of Cape Town, Newlands and Stellenbosch, you’ll find Bartholomeus Klip to be another world of utter tranquillity. It’s an upmarket destination, below a spectacular mountain range and comprises a working farm with wheatlands, flocks of sheep but also a game reserve with buffalo and a tortoise breeding project. The contrast between the two worlds of conservation and agriculture is as far as we know unique in South Africa and makes for a fascinating visit. There is ample walking, canoeing and birdwatching right from your front door or you can use the splendid surroundings to switch off and relax. There are only five rooms in the farmhouse so there are never more than ten guests staying at a time.

    You are welcome to make the house your own, perhaps in one of the reception rooms where an open fire crackles in the winter months, or on the broad verandah that winds around the house and catches the late afternoon sun. There are four double rooms with bathrooms in the beautifully furnished farmhouse and one separate suite outside, with its own secluded verandah looking over the veld and up to the mountains. Finishes everywhere are luxurious and stylish, with crisp cotton bedding and elegant fabrics.

    Your home away from home:

    Bartholomeus Klip
    www.bartholomeusklip.com
    Elandsberg Nature Reserve, Riebeek Valley
    Tel +27 22 448 1087

  • Your Travel Time

    Today's ride is 68km.

  • Your Activities

    The cycling today takes you north from Stellenbosch up the Helshoogte Pass which is a long but highly worthwhile climb to reach the summit. After this, if there is time we’ll cycle on to Franschhoek for a look around this lovely town and either stop off there or at Val de Vie which is more on our way north.

  • Your Food

    The restaurant at BK deserves special mention. Resident Chef Louise Gillett’s imaginative fusion of traditional South African and classic recipes, made mostly from a variety of local ingredients, produce an ongoing feast of delicacies, all day long, from breakfast over brunch and lunch to high tea and dinner.

Day 6
Wellington to Tulbagh via Bainskloof Pass

Mountain Pools & Pedals

  • Your Accommodation

    The Tulbagh Hotel’s buildings date from the late 1800s and in fact so does most of the street: two of the hotel’s rooms look out on to this beautifully preserved streetscape. You’ll be delighted to hear that there’s also a spa on site. You’re staying in the Honeymoon Suite which has been created inside the original carriage house of the building: expect open thatch ceilings, two fireplaces and an intimate lounge area. The hotel offers three pool areas, free Wi-Fi throughout and an in-house beauty therapist. All areas have air conditioning and there are cosy wood-burning fires for winter evenings.

    Your home away from home:

    Tulbagh Hotel
    www.tulbaghhotel.co.za
    22 Van der Stel Street, Tulbagh
    Tel +27 23 230 0071

  • Your Travel Time

    Today's ride is 80km's.

  • Your Activities

    We leave Bartholomeusklip today, heading south back through Wellington to cross the Bainskloof Pass. If the weather’s fine, we’ll take a dip in one of the cool mountain pools along the way. Our lunch stop is the Bistro at the Bergsig Estate which is just after the downhill section of the Bainskloof Pass.We leave Bartholomeusklip today, heading south back through Wellington to cross the Bainskloof Pass. If the weather’s fine, we’ll take a dip in one of the cool mountain pools along the way.

  • Your Food

    Our lunch stop is the Bistro at the Bergsig Estate which is just after the downhill section of the Bainskloof Pass.

    The Tulbagh also offers two in-house sustenance options: their Karee Wine Bar offers local draught beers, craft gin cocktails and a wide selection of local wines. There is a tapas menu, with a South African influence, and gourmet pizzas from the wood fired oven and also the Olive Terrace Bistro offers à la carte breakfast, lunch and dinner menus. The emphasis is on sourcing local fresh seasonal produce, the menu changes weekly, and is an eclectic celebration of South African and international cuisine, including vegetarian, vegan and gluten free options. The bistro has cosy fireplaces for winter, and a beautiful terrace and courtyard for summer al fresco dining.

Day 7
Tulbagh to Boschendal, and Homeward Bound

Cycling Finale at Boschendal

  • Your Accommodation

    Boschendal has so much to offer it’s at first a little overwhelming: apart from the obvious wine tasting and wine sales, they offer a dining option and an informal café (both of which are simply excellent) along with a delicatessen, over 200km of mountain biking trails, lush and verdant gardens, picnics on the ample lawns under shady trees as well as concerts and events all year round. You could stay forever!

    Your home away from home:

    Boschendal
    www.boschendal.com
    Pniel Road, Groot Drakenstein, Franschhoek
    Tel +27 21 870 4200

  • Your Travel Time

    Today's ride is 40 km's.

  • Your Activities

    On your last day, you’ll be collected from The Tulbagh Hotel and driven to Boschendal for your last ride of the trip.

    We’ll be renting mountain bikes directly from Elrico who runs the mountain biking concession at the estate: there is a large variety of trails from an easy 6km to a bone-rattling 40km Black XXL run so take your pick! Elrico can also guide you on any of the trails. Your driver Chris Hannival will be available to take you back to the airport.

  • Your Food

    After your ride, there are great showering facilities and of course the pick of Boschendal’s eateries for refreshment.

YOUR JOURNEY ENDS HERE

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Contact Us

Exceed House
Springfield Office Park
Belleville, Cape Town
7450

Cell / WhatsApp +27 72 136 9096

WhatsApp +27 72 136 9096

Email: travel@whereitallbegan.co.za

Contact Us

About

We’re an ethical private travel planning company focused on Southern Africa.

We offer ready-made and also customised holidays and journeys across this unique region of the world.

When our clients travel with us, they are assured that their travel spend is directly supporting local African companies that offer sustainable products and services, both in terms of people and planet.

Ethos

Our logo is an image of a skull found in the Rising Star Cave System in Gauteng, South Africa in 2013. It was named ‘homo naledi’, meaning ‘human of the stars’.

The cave system has so far given rise to the remains of over 15 individuals, making it the largest hominid fossil remains site ever discovered.

Travelling to Southern Africa is truly a return to the source of humankind, to Where It All Began.

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