Sketching the Cape Winelands 2026
South Africa
with Taria Dawson of Taria's Sketchy Adventures, Urban Sketching World and the author of The Beginners Guide to Urban Sketching
Key Information
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 – Franschhoek – Worcester – 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 – Welcome to the Mother City!
(Cape Town)
Saturday 6th September 2025
Our adventure begins at a stunning beachfront hotel, where you’ll be greeted by breathtaking views of Table Mountain rising across the water. Take a deep breath of the salty ocean air as we gather for an inspiring introduction with Taria, who will set the stage for the days ahead—sharing tips, ideas, and plenty of creative inspiration to get your sketching journey off to a great start.
From there, we dive into the vibrant energy of the Neighbourgoods Market, nestled within the historic Old Biscuit Mill. The scent of fresh pastries and roasted coffee fills the air as we explore this bustling hub of local artisans, food vendors, and musicians. Taria will lead a mini-workshop on capturing movement and atmosphere in a lively market setting, then you’ll have time to wander, sketch, sample delicious treats, and soak up the creative buzz at your own pace.
Next, we make our way to the iconic V&A Waterfront, where Table Mountain provides a breathtaking backdrop to a picturesque harbour filled with boats, street performers, and cafés. Taria will demonstrate techniques for sketching dynamic waterfront scenes, after which you’ll have time to sketch alongside fellow artists, letting the rhythms of the harbour inspire your pages.
DAY 2 – Capturing the Soul of Cape Town
(Cape Town)
Sunday 7th September 2025
Today, we’ll dive into the rich history and vibrant culture of Cape Town through our sketches. As we explore some of the city’s most historic and picturesque locations, our expert guide, Annie, will bring the past to life with fascinating stories of the people and events that shaped this incredible place.
In the morning, we’ll settle into a beautiful spot—perhaps beneath the shady trees of a historic garden or in the midst of colourful, character-filled streets—where Taria will offer guidance on capturing the essence of place through sketching. You’ll have time to experiment, observe, and let your creativity flow.
Later, we’ll take a scenic drive up Signal Hill, where breathtaking panoramic views stretch across the city, Table Bay, and the distant mountains. Watch as paragliders launch into the sky, floating effortlessly above Cape Town, and take the opportunity to capture the drama of the landscape in your sketchbook.
As the day winds down, we’ll return to the hotel before gathering for a relaxed dinner at a beautiful restaurant, where we can reflect on the day’s adventures while enjoying sweeping views of Table Mountain bathed in the evening light.
Overnight in Cape Town.
Please note: Cape Town’s weather can be unpredictable, and we may need to adjust our plans if rain makes an appearance!
DAY 3 – A Journey Along the Edge of the World
(Cape Town)
Monday, 8th September 2025
After breakfast, we embark on one of the most breathtaking drives on the planet—the legendary Chapman’s Peak Drive. This winding coastal road clings to the mountainside, offering jaw-dropping views of towering cliffs, endless ocean, and crashing waves below. With every turn, the scenery becomes more dramatic, making it an irresistible subject for a quick sketch or two along the way.
Our journey leads us to the charming Simon’s Town, home to the South African Navy and an even more adorable local population—a colony of endangered African penguins! These delightful little creatures waddle along the soft sandy shores, giving us the perfect chance to capture their quirky personalities in our sketchbooks (crowds permitting). But there’s more to Simon’s Town than just its famous residents—it’s a place brimming with history, beautiful old buildings, and a relaxed coastal vibe that invites exploration and creativity.
For lunch, we have a special treat—a meal at a restaurant in the sea! Yes, you read that right. Nestled in the waves, this hidden gem lets you enjoy fresh seafood (or other delicious options) with the sound of the ocean all around you. Don’t worry—you won’t get wet, but the experience is sure to be unforgettable!
After a full day of inspiration, we’ll return to our hotel, where the evening is yours to enjoy at your own pace. Take a sunset stroll along the beach, sip a drink with Table Mountain silhouetted against the evening sky, or simply relax with your sketchbook, capturing the magic of Cape Town as day turns to night.
Overnight in Cape Town.
DAY 4 – Sketching, History & Fine Wine in the Cape Winelands
(Cape Town – Stellenbosch – Franschhoek)
Tuesday 9th September 2025
After breakfast, we leave the coast behind and journey into the heart of South Africa’s famous Cape Winelands. A scenic one-hour drive brings us to Stellenbosch, a town brimming with history, oak-lined streets, and iconic Cape Dutch architecture. After dropping our bags at the hotel, we set off for Franschhoek, a charming town with a fascinating past.
Originally settled by French Huguenots in 1688, Franschhoek still carries a strong European influence, reflected in its elegant buildings, boutique cafés, and deep-rooted wine culture. As we explore its cobbled streets and historic sites, we’ll take time to sketch, soaking up the town’s unique blend of French heritage and South African charm.
Of course, no visit to Franschhoek would be complete without indulging in what it’s best known for—its world-class wine. In the afternoon, we’ll visit a stunning vineyard estate, where we’ll sketch the graceful curves of Cape Dutch architecture, surrounded by rolling vineyards and mountain views. Then, it’s time to relax and savour a wine tasting paired with delicious seasonal food platters. This is the perfect way to unwind, reflect on the day’s sketches, and enjoy the flavours of the region.
As the day winds down, we return to Stellenbosch, where your evening is free to explore. Our centrally located hotel puts you within walking distance of a variety of lively bars, cozy cafés, and exceptional restaurants—the perfect setting for a relaxed night out or a quiet evening sketching over a glass of local wine.
Overnight in Stellenbosch.
DAY 5 – Coastal Wonders & Cave Dining in Hermanus
(Stellenbosch – Hermanus)
Wednesday 10th September 2025
After an early breakfast, we set off on a spectacular two-hour drive to Hermanus, a breathtaking coastal town known as one of the best whale-watching spots in the world. As we follow the scenic route along the ocean’s edge, keep an eye out—you might just catch a glimpse of dolphins or even a Southern Right Whale breaching in the distance (although we will be ever so slightly out of season, it could still happen)!
Upon arrival, we’ll settle into a stunning sketching location overlooking the rugged coastline, where Taria will demonstrate techniques for capturing the textures of rocks, waves, and windswept landscapes. Breathe in the fresh sea air as you put pencil and brush to paper, letting the rhythm of the ocean inspire your sketches. And if we’re lucky, we may even have some giant, gentle visitors appearing offshore!
For lunch, we have something truly special—a meal inside a cave! Nestled right at the water’s edge, this one-of-a-kind restaurant offers a unique dining experience where, when the tide is out and the weather allows, you can sit at tables set up on the rocks just meters from the waves. It’s an unforgettable setting to enjoy delicious food while feeling completely immersed in the elements.
Please note: getting to the cave requires navigating several steps.
After lunch, take some time to explore the charming town of Hermanus, known for its boutique shops, art galleries, and incredible coastal scenery.
On our way back to Stellenbosch, we’ll take the dramatic Sir Lowry’s Pass, winding through towering mountains and rolling vineyards. Along the way, we’ll stop at a famous padstal (farmstall), where you can sample local treats, pick up handmade goods, and soak in the countryside charm.
Overnight in Stellenbosch.
DAY 6 – From Desert Edges to Mountain Passes & Timeless Vineyards
(Worcester & Paarl)
Thursday 11th September 2025
After breakfast, we embark on another spectacularly scenic drive, passing through the famous Huguenot Tunnel, a dramatic gateway leading us into a whole new landscape. Emerging on the other side, we arrive in Worcester, a small town perched on the edge of the vast Karoo desert. Here, we’ll take some time to sketch its charming historic buildings, capturing the contrast between old-world architecture and the striking, open landscapes beyond.
Next, we head to a true architectural masterpiece—the Bosjes Chapel. Nestled in the heart of the mountains, this breathtaking structure, inspired by Psalm 36:7, features flowing, organic lines that seem to rise effortlessly from the earth. With its reflective pools, dramatic curves, and stunning natural surroundings, it’s a dream location for sketching. Taria will demonstrate techniques for capturing its unique form and the interplay of light and shadow before you have time to sketch, explore the beautiful gardens, and enjoy a light lunch in this tranquil setting.
From here, we take the thrilling route along Bainskloof Pass, a historic mountain road built in 1849. As we wind our way through rugged cliffs, lush valleys, and tumbling waterfalls, keep an eye out for the leopard warning signs—though sightings are rare, the wilderness here is alive with mystery! With epic views around every bend, this is one of the most dramatic drives in the region.
Our final stop of the day brings us to the historic town of Paarl, a renowned wine region with a rich past. Here, we’ll visit Laborie Wine Estate, one of the oldest wine farms in South Africa, dating back to 1691. The beautifully preserved manor house, with its Cape Dutch elegance and centuries-old vineyards, provides the perfect backdrop for an afternoon of sketching and wine tasting. Sip award-winning wines, soak in the peaceful atmosphere, and capture the timeless beauty of this historic estate.
As the sun sets, we return to Stellenbosch for another relaxing evening.
Overnight in Stellenbosch.
DAY 7 – A Final Day of Inspiration in Stellenbosch
(Stellenbosch)
Friday 12th September 2025
On our final day together, we immerse ourselves fully in the charm and energy of Stellenbosch—a town rich in history, culture, and an undeniable artistic spirit. Known for its world-renowned university, stunning Cape Dutch architecture, and vibrant food scene, Stellenbosch is a true treasure.
Today, we’ll sketchcrawl through its picturesque streets, capturing everything from quaint colonial buildings and lush, tree-lined avenues to the bustling cafés and vibrant marketplaces. Taria will guide you in honing your skills while taking in the atmosphere of one of South Africa’s oldest towns (it might just be the oldest!). With its mix of history and modern flair, Stellenbosch offers an endless supply of inspiration for your sketchbook.
As we conclude our day, we’ll gather for a beautiful farewell dinner at one of the town’s highly rated, award-winning restaurants. With delicious local food and wines to savor, we’ll raise a glass to the friendships formed and the incredible sketches created over our time together. It’s the perfect chance to share your sketchbooks, exchange stories, and reflect on the artistic journey we’ve shared.
Overnight in Stellenbosch.
DAY 8 – Return to Cape Town – End
(Stellenbosch – Cape Town)
Saturday 13th September 2025
After breakfast, we will return to Cape Town, where you can continue your trip independently.
What's included?
Cost
US$2985 per person
Non-sketching partners / friends are welcome
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, Day 5
- Dinner on Day 1, Day 2, Day 7
- Wine tasting on Day 4, Day 6
Excluded:
- Additional drinks, snacks and meals not listed in the itinerary
- Art materials
- Tips
- Personal items
- 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.
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.