Sketching the Cape Winelands 2025
South Africa
Dates: Saturday 6th – Saturday 13th September 2025
Duration: 7 Nights / 8 Days
Start: Cape Town, South Africa
End: Cape Town, South Africa
Group size: maximum 10 people
Highlights: Cape Town – Stellenbosch – Franschoek – Worcester – Wellington – Paarl – Hermanus
Some of the oldest buildings in South Africa. Cape Dutch architecture. Spectacular mountain views. World-class wine estates. Incredible food.
Itinerary
Day 1
Cape Town
Saturday 6th September 2025
We will meet at the hotel on the beach with stunning views of Table Mountain across the water.
Taria will set you up for the trip ahead with what to expect and give you lots of inspiration for the days ahead.
We’ll move on to the hustle and bustle of the famous Neighbourgoods Market held within an old biscuit mill. Taria will host a short workshop on collecting sketches from such a location. Wander around at your leisure, buy some snacks and souvenirs or spend time sketching. The choice is yours.
After a regroup, we will head to the iconic V&A Waterfront with spectacular views of Table Mountain, a beautiful harbour and all manner of entertainment. Taria will demonstrate some more scenes here and then you’ll spend some time sketching.
As we move into the late afternoon/early evening we will head back to the hotel. Later we will have dinner at a beautiful little local restaurant to celebrate our first day together!
Overnight in Cape Town.
Day 2
Cape Town
Sunday 7th September 2025
We will spend the morning sketching some of the historic sights of Cape Town. Annie, our guide, will tell us more about the places we visit. We will also take a drive up to Signal Hill to appreciate the full majesty of Cape Town city below our feet. You may also see a paraglider or two launch themselves from the hill to sail across the city.
We’ll finish the day in a restaurant close to our hotel with magnificent views of Table Mountain across the water.
Overnight in Cape Town.
*Please note: the weather in Cape Town is notoriously changeable. Last minute adjustments may need to be made if it starts to rain!
Day 3
Stellenbosch
Monday 8th September 2025
After breakfast, check out of the hotel and we’ll take a short drive (approx 1 hour) to the historic university town of Stellenbosch.
Stellenbosch is one of the oldest towns in South Africa and has the architecture to match. It’s an absolute haven for keen sketchers! We shall take a short walking tour after which we will head to a nearby wine estate for some lunch.
Taria will demonstrate how to capture some of the scenes around the estate after which you can sketch at your leisure. We will finish our day with some wine tasting!
Overnight in Stellenbosch.
Day 4
Hermanus
Tuesday 9th September 2025
After breakfast we will drive to Hermanus (approx 2 hours), a beautiful coastal town famous for whale watching.
Taria will demonstrate how to capture some of the textures of the coast and you’ll be able to sketch for a while, enjoing the fresh coastal air and perhaps even spotting a whale out in the Atlantic ocean.
Lunch will be at an iconic restaurant inside a cave! When the tide is out and the weather ok, tables are even set up on the rocks right next to the ocean. There are several sets of steps to get down to the cave. After lunch, browse the town and enjoy the incredible scenery.
We’ll return to Stellenbosch via a beautiful mountain pass, Sir Lowry’s Pass, stopping at a famous padstal (farmstall) along the way.
Overnight in Stellenbosch.
Day 5
Franschhoek
Wednesday 10th September 2025
A short drive (approx 30 mins) from Stellenbosch is the historic town of Franschhoek, rich with history of the French Hugenots who settled there in 1688. Franschhoek has a strong cultural identity as well as famous vineyards surrounding it. We shall spend the morning learning about the heritage of the town, along with sketching activities.
It would be rude not to sample some wine in the afternoon. We’ll take a short drive to one of the famous wine estates to sketch some of the finest examples of Cape Dutch architecture in the country. Followed by wine tasting accompanied with seasonal food platters.
Overnight in Stellenbosch.
Day 6
Worcester, Wellington & Paarl
Thursday 11th September 2025
After breakfast we will take a spectacularly scenic drive through the famous Hugenot Tunnel to the small town of Worcester, right on the edge of the Karoo desert. We will sketch some of the iconic buildings before taking another scenic drive to The Old Tannery in Wellington. The building dates back to 1871 and is one of the oldest factories in South Africa. It has undergone redevlopment and is now home to offices, handicrafts, a craft brewery and even a classic car cafe. Yes, there is plenty to sketch here. The names of the craft beer are worth the visit alone…you’ll see what we mean!
We’ll venture forth to Paarl, another historic town and home to more award-winning wines. We’ll visit one of the oldest wine farms in the region, Laborie. The estate dates back to 1691 and the manor house has been preserved beautifully. This is where we’ll finish the day with some wine tasting.
Overnight in Stellenbosch.
Day 7
Stellenbosch
Friday 12th September 2025
On our final day together, we will enjoy all that Stellenbosch has to offer. Wonderful atmosphere, incredible buildings, amazing food. We shall sketchcrawl our way around the town and end our day with a beautiful goodbye dinner at one of the highly-rated restaurants and share our sketchbooks.
Overnight in Stellenbosch.
Day 8
Transfer back to Cape Town - End
Saturday 13th September 2025
After breakfast we will return to Cape Town where you are free to continue your trip independently.
Cost
US$2985 per person
What's included?
Included:
- All accommodation (your own private room in hotel)
- Breakfast
- Transport & driver
- Tour guide
- Art instruction
- Entry fees where applicable
- Lunch on Day 3, Day 4
- Dinner on Day 1, Day 2, Day 7
- Wine tasting on Day 3, Day 5, Day 6
Excluded:
- Additional drinks, snacks and meals not listed in the itinerary
- Art materials
- Tips
- Personal items
- International flights
- Transfers to and from Cape Town airport
How to book
A deposit of US$500 is required to reserve a space on this trip. The balance of the trip is required 60 days prior to departure.
Please email Taria: taria@prettysketchy.tours – and she will send an invoice for payment.
Photo Gallery
Additional Information
If you need any advice and recommendations for further travel in South Africa, just let us know and we can point you in the right direction.
We highly recommend taking further time to explore Cape Town and the Western Cape region. If you have time and ability we also recommend a visit to the world-renowned Kruger National Park to spot the Big Five! If you’re more into road-tripping and beautiful scenery then the Garden Route is a must.