A beautiful picture of the The Cape Winelands (+ Cape Town and the Overberg) tour

The Cape Winelands (+ Cape Town and the Overberg)

Tour Duration

8 Nights

Starting From


Tour Highlights:

The picturesque Cape Peninsula
The majestic Winelands landscapes
Whale watching on the Overberg coast

The Cape Winelands (+ Cape Town and the Overberg)



Your adventure starts with three nights at Parker Cottage in Cape Town. You’re then taken on a guided tour of the Cape Winelands, staying two nights at the Garden House in Franschhoek. You’ll then be guided through the Overberg before spending your last two nights at Schulphoek right on the cliff tops in Hermanus. You fly onwards from Cape Town.


Your journey begins here

DAYS 1 - 4

Parker Cottage

You’ll be met by Chris Hannival from Cape Town International and taken directly to Parker Cottage. The first afternoon and evening is free to allow you to acclimatise and enjoy many of the great eateries in the area, perhaps taking the Cable Car to the top of Table Mountain if there's time.

Parker Cottage is a fascinating building, having worn many hats in her long years in Cape Town. Built originally as a Victorian gentleman’s residence by the then mayor of Cape Town, John Parker, it went through many roles as student accommodation and a photographer's studio.  It has been extended and turned finally into Cape Town’s premier B&B.  Pamela Nayler, the owner, has themed each room individually, retaining and restoring the marvelous charming features of the building.  The breakfast menu here is to die for: over 16 'specials' on top of the traditional cooked breakfast!

There is so much to do in Cape Town that you might need a little help! Tomas and Pamela will have lots of ideas but of course we’re on hand to help you too with transport, tickets and reservations as you need them for Robben Island, walking tours, and Cape Town’s many museums. If all that is a bit too sedate for you, October is a great month to go paragliding as the summer winds have not yet arrived and the winter rains are largely over. You don’t get a better view of the city than by flying (silently) over it.


3 Carstens Street, Tamboerskloof, Cape Town
Tel +27 21 424 6445

Parker Cottage

A beautiful picture of Parker Cottage

Another beautiful picture of Parker Cottage
Your journey continues


Cape Peninsula Tour

On the morning of your second day, you’ll be collected either by Chris Hannival or Ron Martin, your guides and drivers for this and all your tours, for your day trip to the Cape Peninsula.  Depending on traffic, Ron or Chris will be at Parker around 09h30.  You should expect to be back at Parker Cottage around 17h00.

The vast array of things to see and do on the Cape often leaves first-time visitors utterly bewildered: the Cape is a wine region in its own right, boasting over eight wine estates some dating back into the 17th century.  Add on to this the very pretty collection of old Victorian seaside towns, the South Africa 'cinque terre', connected by a rickey railway line, the penguins at Boulder's Beach and then the rugged dagger of rock that is Cape Point, reaching out towards Antartica and you are just spoilt for choice as to what to see and where to go!

Chris will give you a full briefing of the possibilities, particularly in terms of weather as ti can be very variable, on the day. You can choose to focus the day on the wildlife (marine and terrestial), the wine and food, the history and architecture or the beaches and scenery, to name but a few.

Cape Peninsula Tour

A beautiful picture of Cape Peninsula Tour

A beautiful picture of Cape Peninsula Tour
Your journey continues


Cape Winelands Tour

You’ll be picked up by Chris Hannival for your tour of the Cape Winelands around 09h30 (depending on traffic).

Visiting the Cape Winelands is without a doubt a must-do. Even if you aren’t that interested in actually drinking wine, the rest of the attactions in the region, not to mention the spectacular nature beauty of the place, astounds most visitors. There are over eight winelands towns (all very pretty and different from one another), numerous villages and in excess of 1500 wine estates. We have never met anyone who has been to all of them!

Bear in mind that the Winelands are about far more than just wine: the region pours with creativity and history, particulary in the realm of food. The scenery is stunningly beautiful and the range of olives, chocolate, port, brandy, cheese, fruit are world class. On top of this, the towns and villages are architecturally fascinating and Stellenbosch boasts the third largest university in the country.The farmhouses of the Cape Winelands are really country mansions in disguise!

Cape Winelands Tour

A beautiful picture of Cape Winelands Tour

A beautiful picture of Cape Winelands Tour
Your journey continues

DAYS 5 & 6

The Garden House

Chris will drop you off at The Garden House after your tour around 17h00.

Owners Barry and Annette at The Garden House have been the highest rated B&B in the village for so long now, it’s almost become cast in stone: Annette is particularly involved with animal rescue so if you manage to escape your stay without suddenly having been made parent to a stray cat or dog, you’ve done very well! Boasting only two rooms, this is home stay B&B like no other: your privacy is sacred and the breakfasts in the garden cannot fail to set you up for a hard day’s wine tasting and strolling in the village.

Once a sleeply little town in the winelands, Franschoek was discovered by wealthy Capetonian émigrés about twenty years ago. Now, Franschoek is a very pretty and upmarket town surrounded by stunning scenery and agri/viti culture that is very much on the tourist route from Cape Town. From its name and those of the surrounding farms you’ll be able to tell that this is the French part of South Africa, so expect excellent food and wine along with a proud cultural history. If you thought house prices were bad in Camps Bay, think again for the price of a two-bed cottage here!

We suggest that you explore the town on foot. The place is bursting with all sorts of little boutiques and some great restaurants too: rather avoid the overpriced and pretentious Le Quartier and instead, try some of the smaller local eateries like Le Bon Vivant. We can send a list of suggestions but Annette and Barry have their finger on the pulse too.

29 De Wet Street, Franschhoek
Tel +27 21 876 3155

The Garden House

Another beautiful picture of The Garden House

A beautiful picture of The Garden House
Your journey continues


Overberg Tour

Chris or Ron will collect you from the Garden House around 09h30 for your tour of the Overberg.
The Overberg is a large area and not as close to Cape Town as the Cape Peninsula and Cape Winelands. For this reason, most first-time visitors to Cape Town often don’t venture this far and would rather stick to the more predictable, tourist-friendly routes. However, the Overberg is truly an amazing region and makes for a destination in its own right. Depending on time, Chris or Ron will take you through the following attractions and towns:
• Gordons Bay – a beautiful and very much underrated seaside town
• Clarence Drive (which connects Gordons Bay to Klienmond via Betty Bay) is a stunning coastal road equal in beauty to Chapmans Peak but longer, less busy and with more stop offs.
• Bettys Bay Beach with its many wild penguins is far nicer than its cousin Boulders Beach mainly because it takes much longer to get here and you can only really do it by private transport so there are far fewer tourists.
• The Kogelberg Biosphere is officially the world’s most complex biodiversity site by square kilometre and merits a whole day trip on its own.
• The Harold Porter Botanical Gardens which are small but no less impressive than their big sister Kirstenbosch and both run by SANBI to a very high standard.
• Hermanus itself (your destination) which has transformed itself from an old whaling town into a vibrant retreat for Capetonians. You can do whale watching by boat, kayak or land-based here.
• The Hemel en Aarde Valley (the R320 which connects Hermanus to Caledon) is a delightful meander of world-class wine estates and food, and is far easier to navigate than the myriad vastness of Stellenbosch and Franschoek.

Chris or Ron will drop you off at Schulphoek, your accommodation for tonight, around 17h00.

Overberg Tour

Another beautiful picture of Overberg Tour

Another beautiful picture of Overberg Tour

Another beautiful picture of Overberg Tour
Your journey continues

DAYS 7 and 8


Hermanus used to be called Hermanuspietersfontein: it’s pretty easy to see why the name got changed! But that ‘fontein’ (‘fountain’ or ‘spring’) in English is still alive and well and continues to bubble just a few steps from the seashore. In fact, the village of Hermanus grew around the spring and the building that La Fontaine is located in is one of the first houses ever built there.

Founded in 1999, Schulphoek House offers understated luxury and Cape refinement to its guests. Fully renovated and expanded in 2017 to 15 en-suite bedrooms; there are 9 spacious, modern and well appointed sea facing en-suite rooms and 6 comfortable en-suite garden rooms.

Schulphoek House is set on the protected Schulphoek bay in Sandbaai (Sand Bay), 4 km from Hermanus center. The bay is a place of tranquility; home to cove dwelling marine life and a place of respite for visiting Southern Right whales during their annual calving season. Schulphoek House takes great pride in its cuisine and wine offering. The wine has been curated from the Hemel-en-Aarde region. The dinner menu is limited to fresh and locally sourced ingredients; venison from the nearby Karoo region and fresh fish sourced from local fishermen. Dedicated gardeners produce small crops of baby vegetables and herbs for the kitchen.

Fingers crossed that for the two days you are in Hermanus the sea state and the weather will combine to allow you to spend some time on the water observing the Southern Right and Bryde whales that come close to the shore here every year between June and December to calve. We’d be happy to arrange for a boat or a kayaking trip so please do let us know if you’d like to give that a try.

If the weather or sea state don’t play ball, the town of Hermanus itself has a lot to see and do, including the magical Cliff Path which is 12km long and passes through rock pools, look-out points and lots of the Cape fynbos, which is filled with local birdlife. There are also many nature reserves in or near the town, one of the nicest being Fernkloof Nature Reserve which has well signposted hikes from 45 minutes to 3 hours. There are many small secluded beaches in the area and on the larger beaches like Grotto Beach you can take the opportunity to horse ride through the surf. Of course we’re on hand to arrange anything you’d like to do.

You’ll be collected from Schulphoek by either Chris or Ron for your transfer to Cape Town International Airport, and your flight home.

181 Piet Retief St Sandbaai, Hermanus, South Africa
Tel +27 28 316 2626


A beautiful picture of Schulphoek

Another beautiful picture of Schulphoek
Your journey ends here
Why is this Ethical ?

80% of the accommodation is run ethically and 100% of the guiding and transport is ethically sourced

See Similar Custom Journeys

Read Travel Guides Related To This Journey

Enquire About This Journey
Share This Journey

Dynamic Map

(use CTRL + scroll to zoom in or out)

Contact Us

Exceed House
Springfield Office Park
Belleville, Cape Town

Office +27 21 424 5347
Cell +27 72 136 9096

WhatsApp +27 72 136 9096

Email: travel@whereitallbegan.co.za

Skype: philrendel

Contact Us


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.


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.

Whatsapp Icon
This email address is being protected from spambots. You need JavaScript enabled to view it.