Day notes
Step into the soul of the Cape Winelands with a delightful day trip to Stellenbosch, a historic gem bursting with energy, charm, and old-world character. Known for its lively student vibe, oak-lined avenues, and rich heritage, this buzzing university town offers the perfect blend of culture, history, and irresistible local flavor.
Forget the car today—the heart of Stellenbosch is best explored on foot. We'll wander along the iconic Dorp Street, one of the oldest and most scenic streets in South Africa, lined with beautifully preserved Cape Dutch architecture, quaint cafés, and boutiques that invite you to linger.
No visit is complete without a stop at the famous Oom Samie se Winkel—a nostalgic treasure trove of local treats, vintage curios, and true South African charm. It's like stepping into a time capsule, with every shelf telling its own story.
Surrounded by world-class wine estates, the town offers more than just a taste of good wine—it delivers an unforgettable cultural experience right in its vibrant town centre.
Transfer from Cape Town International Airport [CPT] to Historic Stellenbosch
Transfer
Cape Town International Airport [CPT]
Historic Stellenbosch
Hike from Historic Stellenbosch to Dorp Street
Hike
Historic Stellenbosch
Dorp Street
Hike from Dorp Street to Oom Samie se Winkel
Hike
Dorp Street
Oom Samie se Winkel
Transfer from Oom Samie se Winkel to Vendôme Wine Estate
Transfer
Oom Samie se Winkel
Vendôme Wine Estate
Check-in to Vendôme Wine Estate
Included:
- Guided Orientation Walk of Stellenbosch Town Centre
- 2 Night Stay at the beautiful Vendome Wine Estate
Excluded:
- All museum entrances
Day notes
Step off the beaten path and into the soul of the Cape Winelands with “Paarl Past & Pour”—an unforgettable blend of storytelling, architecture, and wine, all set against the backdrop of one of South Africa’s oldest towns.
Your journey begins with a leisurely 1km guided walk along Paarl’s picturesque main street, where majestic manor houses whisper tales of centuries past. With a local guide from the valley leading the way, you'll uncover hidden histories, marvel at Cape Dutch architecture, and explore the birthplace of business in the area—right around the historic Strooidak Church.
Peek into the past with a visit to:
The oldest remaining working well in Paarl
One of the town’s earliest dwellings, dating back to 1784
And the mysterious “Die Kraan”—a little-known piece of Paarl folklore you just might get to see!
Along the way, meet the spirited characters who once called these grand homes their own, and uncover the lesser-known stories that shaped this Winelands jewel.
But what’s a day in the Winelands without a toast to its finest offering? After your walk, we’ll head to one of the Drakenstein Valley’s beautiful wine estates for a relaxing tasting experience surrounded by vineyard views.
To end on a high note, we'll visit the Afrikaans Taal Monument, an iconic tribute to language, culture, and the people who shaped it—set against breathtaking panoramas of the valley.
Included:
- Guided Historic Walk
- Wine Tasting Experience
- Entrance to the Taal Monument
Excluded:
- Lunch and other meals & beverages not specified as included
- All personal expenses
Day notes
Today’s adventure take us past Drakenstein Correctional Services and to begin in the heart of one of the Cape Winelands’ most enchanting villages—Franschhoek, the "French Corner" of the Cape. We’ll take a slow and easy stroll along the Main Road, a treasure trove of boutiques, art galleries, and cozy coffee shops, each with its own character and charm waiting to be discovered.
Your guide will drop you off at one end of this walkable, vibrant street and meet you at the other, giving you the freedom to explore at your own pace. As you meander your way upward, framed by majestic mountains and lined with shady trees, the impressive Huguenot Monument slowly comes into view, standing proudly at the head of the road—welcoming and watching your approach.
For those who wish, the Huguenot Gardens and Museum offer a peaceful pause, where stories of early French settlers and their lasting influence on the valley unfold in a beautifully curated setting.
But the journey doesn’t end there…
We continue with a drive over the breathtaking Franschhoek Pass, where panoramic views stretch out across valleys and vineyards. Along the way, we’ll stop to admire the Theewaterskloof Dam—a vital water source that just a few years ago stood hauntingly empty during the drought. Today, it glistens once more, restored and vital, a reminder of nature’s resilience.
The scenic route winds through charming small towns and rolling countryside, leading us onward to our final destination of the day—yest another filled with character!
Step back into a bygone era with an unforgettable overnight stay in the historic village of Matjiesfontein—a true time capsule nestled in the heart of the Karoo.
Upon arrival, we dive straight into the town’s fascinating heritage with visits to the Railway and Transport Museums, where tales of steam trains, Victorian travelers, and Karoo legends come to life among vintage carriages and quirky collections.
Then it’s time to check in at the iconic Lord Milner Hotel, where old-world elegance and period charm await. Expect creaking wooden floors, vintage décor, and a quiet, starlit atmosphere that feels like something out of a classic novel.
But don’t get too comfy just yet—meet us in the hotel foyer around 18h00 for what may well be the shortest—and most entertaining—bus tour in the world! Hop aboard a delightfully quirky ride through town as your guide delivers a spirited commentary filled with laughter, stories, and a few surprises.
As the sun sets over the wide Karoo horizon, the night is yours to enjoy. Relax with a drink on the hotel’s stoep, dine in vintage style, and soak in the stillness of this unique town where time truly stands still.
Check-out from Vendôme Wine Estate
Transfer from Vendôme Wine Estate to Franschhoek Pass
Transfer
Vendôme Wine Estate
Franschhoek Pass
Transfer from Franschhoek Pass to Theewaterskloof Dam
Transfer
Franschhoek Pass
Theewaterskloof Dam
Transfer from Theewaterskloof Dam to Lord Milner Hotel
Transfer
Theewaterskloof Dam
Lord Milner Hotel
Check-in to Lord Milner Hotel
Included:
- Entrance to the Railway Museum
- Entrance to the Transport Museum
- "Shortest Bus Tour in the World"
- Dinner at The Lord Milner Hotel
- Overnight at The Lord Milner Hotel
Excluded:
- Any meals and beverages
- All personal expenses
Day notes
After a restful night in the timeless village of Matjiesfontein, we continue our journey along the evocative Forgotten Route, where each bend in the road unveils landscapes steeped in history and natural grandeur.
Our path winds through the dramatic and lesser-traveled Seweweekspoort, a rugged mountain pass carved by time and water. Towering sandstone cliffs rise on either side, echoing tales of explorers, ox wagons, and the untamed spirit of the Klein Karoo. Keep your camera ready—this is one of the most scenic and soul-stirring drives in the country.
By midday, we arrive at the beloved Kobus se Gat, a true Karoo gem where warm hospitality meets hearty, traditional cuisine. Tuck into authentic South African dishes, lovingly prepared and served with mountain views and rustic charm.
With hearts and stomachs full, our journey continues as we ascend the legendary Swartberg Pass, a national monument and one of the most iconic mountain passes in South Africa. Built by Thomas Bain in the 1800s using little more than pickaxes and grit, the pass winds dramatically upward to the highest point, offering jaw-dropping views across the valleys below.
Breathe in the crisp mountain air, feel the rich history beneath your feet, and take a moment to marvel at the incredible feat of engineering and nature’s raw beauty—this is a place where time slows down and the silence speaks volumes.
Check-out from Lord Milner Hotel
Transfer from Lord Milner Hotel to Seweweekspoort
Transfer
Lord Milner Hotel
Seweweekspoort
Transfer from Seweweekspoort to Swartberg Experience - Kobus Se Gat
Transfer
Seweweekspoort
Swartberg Experience - Kobus Se Gat
Transfer from Swartberg Experience - Kobus Se Gat to Mooiplaas Guest House
Transfer
Swartberg Experience - Kobus Se Gat
Mooiplaas Guest House
Check-in to Mooiplaas Guest House
Included:
- Lunch at "Kobus-se-Gat"
- 3 Night Stay at Mooiplaas Guest House
Day notes
Today’s journey is all about slowing down, tuning in, and experiencing the magic of the animal kingdom with care, curiosity, and deep respect.
We begin before sunrise, venturing out into the soft stillness of the morning for a once-in-a-lifetime experience: a Meerkat Safari ! As the sky gently brightens, we settle quietly in the veld, waiting patiently for these wild, free-roaming meerkats to rise with the sun. Watching them emerge, stretch, and begin their day is nothing short of humbling—a rare glimpse into their world, guided by experts who care deeply about their welfare and habitat.
After a hearty breakfast, the journey continues to the Ostrich Farm, where we learn about the remarkable history and biology of these fascinating birds. This is not just a farm tour—it's a chance to better understand the role of ostriches in the region and the ongoing efforts to treat them with care and dignity. Here, education goes hand-in-hand with conservation, and every visit helps support responsible animal management.
In the golden light of the late afternoon, we make our way to the peaceful surrounds of Buffelsdrift Game Lodge, where we’ll observe the resident elephants in their semi-wild habitat. These gentle giants are ambassadors for their species—each one with a story of rescue and refuge. Watching them up close, from a respectful distance, offers a powerful moment of connection. It’s a chance to reflect on the intelligence, emotional depth, and majesty of one of Africa’s most iconic animals.
Included:
- Sunrise Meerkat Safari
- Tour of Ostrich Farm
- Respectful Observation of Elephants
Day notes
Today, we’ve hit the pause button—no fixed plans, no early alarms, no rush. While we can absolutely arrange another jam-packed day of exploring, we’ve intentionally left this one open for you to unwind, recharge, or choose your own adventure.
Fancy a quiet morning with a book and a view? Go for it.
In the mood for a spontaneous outing? We’ve got a few exciting options up our sleeve—just say the word!
Whether you’re keen to explore more of the surrounding beauty, take a scenic drive, or join visit a Big 5 safari, we’re here to help make it happen.
Day notes
Embark on an unforgettable journey from Oudtshoorn to Arniston, where quirky charm meets breathtaking landscapes. Hit the legendary Route 62, winding your way through dramatic semi-desert scenery toward Barrydale, where time slows down and creativity flourishes.
No trip is complete without a cheeky pit stop at the iconic Ronnie's Sex Shop—a misnamed roadhouse bar plastered with bras, signatures, and good stories. Refreshed and amused, cruise over the spectacular Tradouw Pass, a winding masterpiece carved into the mountains, offering sweeping views of deep gorges and lush valleys. It’s a road trip full of character, colour, and curves—ending in the serene seaside beauty of Arniston.
Check-out from Mooiplaas Guest House
Transfer from Mooiplaas Guest House to Ronnie's Sex Shop
Transfer
Mooiplaas Guest House
Ronnie's Sex Shop
Transfer from Ronnie's Sex Shop to Barrydale
Transfer
Ronnie's Sex Shop
Barrydale
Transfer from Barrydale to Tradouw Pass
Transfer
Barrydale
Tradouw Pass
Transfer from Tradouw Pass to The Arniston Spa Hotel
Transfer
Tradouw Pass
The Arniston Spa Hotel
Check-in to The Arniston Spa Hotel
Included:
- Routing and Stops as mentioned
- 2-Nights at Arniston Spa Hotel
Excluded:
- Any meals and beverages
- All personal expenses
Day notes
Discover the raw beauty and soulful charm of South Africa’s southern coastline on a day that blends nature, history, and heartwarming hospitality. Begin with a self-guided walk to the Waenhuiskrans Cave, hidden beneath the cliffs near Arniston. Accessible only at low tide, this sea-carved wonder is a surreal space of echoing waves and ancient stone—perfect for a quiet moment in nature’s cathedral.
From there, head to Cape Agulhas, the true southern tip of Africa, where the Indian and Atlantic Oceans meet in a dramatic, windswept embrace. Snap a photo at the iconic marker and feel the power of standing at the edge of a continent.
On your way back, wander through Kassiesbaai, a picture-perfect fishing village frozen in time, with its whitewashed cottages and stories etched into every weathered wall. End your day with tea at Mien's, a local gem where warm smiles and homemade treats make you feel like family. It’s a day of discovery, where land, sea, and soul come together.
Expert tips:
A Few Friendly Notes Before We Head to the Cave...
Visiting the Waenhuiskrans Cave is an adventure in itself—and like all good adventures, it comes with a bit of a scramble! Depending on the tide, you’ll either enjoy a gentle walk through shallow water and across some potentially wet, slippery rocks, or descend a short but steep, rocky staircase that Mother Nature herself carved out (no handrails, but plenty of character).
The terrain is uneven and rocky, so sturdy, non-slip shoes are a must—flip-flops won’t cut it here unless you enjoy testing your balance in front of strangers. While the walk is relatively short and suitable for all fitness levels, those with difficulty walking or climbing over low rocks may find it a bit challenging. Take your time, go at your own pace, and feel free to pause for a “wow” moment or two.
If it’s one of those glorious South African summer days, you’ll want to pack a beach towel and your swimsuit—we’ll be passing some postcard-perfect beaches, and T2C never misses a chance to stop and soak in the natural beauty (or dip a toe in the water).
Quick tip: Your shoes may end the day wetter than they started, so it’s wise to bring a dry spare pair. After all, soggy shoes are no friend to happy feet—and we’d hate for anything to distract you from the magic of the day.
Let’s embrace the adventure—wet toes, wild views, and all!
Included:
- Routing and Stops as mentioned
- Tea and Snack at Mien's Tea Garden
Excluded:
- Any meals and beverages
- All personal expenses
Day notes
As we journey from the South Coast to Cape Town, we highly recommend taking the day slow and savoring the stunning scenery along the famous Whale Coast Route. This stretch is more than just a drive—it's a showcase of coastal magic, charming towns, and unforgettable viewpoints.
During whale season, a whale watching boat trip can be arranged for a front-row seat to nature’s grandest performance. Or, if you’re craving a bit of adrenaline, how about sandboarding the dunes in Betty’s Bay? Just don’t miss the chance to visit the Stoney Point Penguin Colony—a quieter, more intimate alternative to Boulders, where you can walk among a bustling African penguin colony.
Wrap up your coastal escape with a drive along Clarens Drive, one of the Western Cape’s most scenic routes, where ocean meets mountain in a breathtaking embrace.
Let's take our time, and let the road to Cape Town become part of the adventure.
Check-out from The Arniston Spa Hotel
Transfer from The Arniston Spa Hotel to Hermanus
Transfer
The Arniston Spa Hotel
Hermanus
Transfer from Hermanus to Stony Point Penguins
Transfer
Hermanus
Stony Point Penguins
Transfer from Stony Point Penguins to Cape Town International Airport [CPT]
Transfer
Stony Point Penguins
Cape Town International Airport [CPT]
Expert tips:
From around June to November, the Whale Coast comes alive as southern right whales return to our shores—offering one of the most spectacular marine experiences in the world.
If you'd like to join a whale watching boat trip, be sure to book well in advance, as these excursions are extremely popular and tend to fill up quickly. A little preparation goes a long way—especially when it comes to motion sickness. Even seasoned sailors can feel the swell, so it’s wise to come prepared to keep the focus on the whales, not your stomach!
Please note: All boat trips are weather and ocean-condition dependent. While cancellations can happen for safety reasons, don’t worry—you’ll have the option to rebook or receive a refund if your trip doesn’t go ahead.
With the right planning, this could be one of the most memorable highlights of your journey!
Included:
- Breakfast
- Entrance to Stony Point Penguin Colony
Excluded:
- Any meals and beverages
- All personal expenses