My Cape Town itinerary turned out nothing like I imagined—and honestly, that’s what made it unforgettable. Instead of sticking to the usual checklist of tourist stops, we ended up diving into the city’s quieter corners, the places you only find when you wander without a plan. We discovered experiences that felt genuine, personal, and refreshingly offbeat. And each day brought a new adventure and made us realize that there’s always more to a city than meets the eye.
1. Thrilling Off-Road Jeep Adventures in Cape Town
Exploring has never felt so freeing! With Jeep Tours Cape Town, founded and passionately led by the inspiring Lizanne, I found myself cruising through the Mother City in an open-top Jeep Wrangler, wind in my hair, sun on my face, and not a single rigid schedule holding us back. Instead of shuffling along with a crowd, we set our own relaxed pace, stopping whenever something caught our eye. Our local guide shared stories about the vineyards, countryside legends, and quirky local anecdotes you’d never hear on a typical tour.
We rolled over soft hills, passed family-run wineries, and glided along coastal roads where the ocean shimmered beside us. One of the highlights was stopping at De Grendel Wine Estate, sipping their refreshing Proposal Hill Rosé with Table Mountain dramatically rising in the distance.
What makes these tours truly special is how personalised they are. Whether you’re in the mood for a wine safari, mountain trails, hidden villages, or scenic coastal gems, everything is designed around your vibe. It’s the kind of experience that makes you feel like you’re exploring the soul of Cape Town, not just ticking off attractions on a list.
2. Wine Tasting Inside Cosy Caves
Wine tasting inside caves isn’t usually a must-have experience, but it should be. Klein Roosboom, Cape Town, is a charming, family-run estate that has transformed old concrete wine tanks into intimate tasting caves, each filled with vintage furniture, warm lighting, and remnants of the original wine stains still etched into the walls. Every cave has its own quirky story and character, making it feel like you’ve stepped into a secret hideout just for you and your friends.
Their wines are equally thoughtful. Each bottle is named after a family member, with a sweet personal note or story printed on the label. It added a sentimental touch that made every sip feel meaningful for us. Whether you’re into earthy reds, smooth whites, or a refreshing rosé, they have a beautifully curated selection.
Of course, wine is best enjoyed with good food, and their platters are generous with farm-style bread, creamy cheeses, biltong, rootstock crisps, seasonal fruits, and even chocolate brownies. You can enjoy it all in the caves or head outside to the tranquil garden for a more relaxed vibe in Cape Town.
3. Firing a Real Cannon!
Firing a real cannon was never on my travel bucket list, mostly because I didn’t think regular humans were allowed anywhere near one. But at the Nitida Cannon Station, that’s exactly what you get to do, and trust me, it’s every bit as wild as it sounds. The team there is incredibly passionate and walks you through everything: the history behind these old cannons, how their mechanics worked, and the precise (slightly nerve-wracking) steps of packing the gunpowder just right.
Grace got the fun job of ringing the giant brass bell, while I was handed the honor of preparing the cannon under expert supervision. Standing there with earmuffs on, fuse in hand, heart racing… I took a breath, lowered my hand and then… BOOM!
Within a blink, there was smoke and blast, starting all of us, and for a few seconds, we just stared in awe, “Did that really just happen?” We laughed and cheered, and I even got a certificate to commemorate the feat. Meanwhile, Paul mastered sabrage and popped open a bottle of Nitida’s sparkling wine so we could celebrate in style. No wonder newlyweds come here to kick off married life with a literal bang. It’s easily one of the strangest, coolest, and most unexpected experiences I’ve ever had on a trip, one I’ll be bragging about for years.
4. Magic Behind Diamonds at Shimansky
Diamonds are a girl’s best friend, and walking into Shimansky, surrounded by hundreds of them, I definitely understood the hype. The tour started with Sana, giving us a deep dive into the history of South African diamonds – how they were discovered, mined, sourced, and transformed into the sparkling masterpieces we adore. She shared fun stories and surprising facts that made the journey feel warm and personal.
A major highlight was trying on pieces from the iconic My Girl collection – the world’s first square-cut diamond. There’s something magical about slipping on a diamond that catches light from every angle. We also learned about Tanzanite, one of the rarest gemstones in the world – and the best are seen at Shimansky.
But the main highlight was meeting Stephan, who explained in detail about diamond polishing. His level of precision, skill, and planning in making each diamond perfect is truly fascinating. We also got a chance to polish a raw diamond. It’s one thing to admire a sparkling jewel in a shop, and quite another to feel the weight of a raw stone, work with it, and see it start to transform. We wrapped up with Cape Town’s local brand of gin and chocolate tasting. I loved the perfect blend of sweet, bitter, and boozy notes – a sparkling way to end the tour.
5. Fun While Cooking at Food Jams
I wasn’t expecting to cook in Cape Town, but Food Jams turned out to be quite fun. This isn’t your usual stand-over-the-cutting-board kind of thing, it’s lively, a little messy, and full of laughs. We kicked things off with drinks and snacks, easing into conversations with the rest of the group before being split into teams and handed a variety of fresh ingredients with guiding recipe ideas.
There is music, laughter, a little friendly chaos, and zero pressure. You can stick to the recipe or go full MasterChef and improvise your own twist. Luckily, our teammate Sarah knew what she was doing, while the rest of us chopped, stirred, and freestyled our way through dishes. With our huge crowd, the menu was just as vast with smoked trout, sea pumpkin risotto, chicken skewers, roasted veggies, tacos, stuffed peppers, and much more. It was a feast and we all sat down together, sharing stories and laughter over our collectively made dishes.
There was also a make-your-own-drink counter where we could learn and experiment to curate a drink best suitable for our taste buds. Food Jams is for anyone who loves good company, good music, and good food… even if you can’t cook to save your life. Just show up, grab a drink, embrace the mess, and enjoy every bite.
6. Wines, Wildlife & Sustainability In A Vineyard
Vergelegen’s Environmental Tour took us on a mini adventure through nature, wildlife, and sustainability. We passed landscapes dotted with indigenous flowers, ancient trees, and sweeping mountain views. We even got a mini safari, as we spotted bonteboks, red hartebeests, black wildebeests, Nguni cattle, and a few Rau quagga, they are a part of their breeding project to bring back these extinct species. Along the way, we learned about the estate’s efforts in sustainability, from rehabilitating fynbos and restoring wetlands to investing in solar power to responsible water management.
The land also boasts a 300-year-old Cape Dutch homestead, a 200-year-old library with 4500+ books from all over the world, and many glorious gardens. After the tour, we relaxed and tried their collection of wines. My favorites, Florence Rosé and Wild Winds Sauvignon, tasted even better knowing the care behind the land.
If you enjoy slow travel, eco-friendly stories, or just want to experience something beyond a normal vineyard tour, Vergelegen is absolutely worth a spot on your itinerary.
At Laurensford Cape Town, we started with a Belgian chocolate and wine pairing, then swapped glasses for a bow and arrow. Guided by expert and patient instructors, we tried archery in the wild, aiming to shoot a fake hidden lion in the bushes or a moving crocodile. It was fun, challenging, and unexpectedly addictive!
Between unique tours, adrenaline-filled adventures, and incredible meals, I was filled with awe and wonder. The people I met made the experiences even richer and each day brought something new and beyond the usual tourist spots. Cape Town offers a mix of wild, thoughtful, vibrant, and offbeat experiences, waiting to be noticed and appreciated – and it will surprise you in the best possible way.
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