Cape Town – Dreams of Africa Begin

I have dreamed of Africa for years, and it’s hard to believe that we finally began a journey that took three years to come to life. We worked with our amazing travel agent, Rachel from Africa and You, who created a custom trip tailored just for us. Little did we know that Covid would hit, borders would close, and time would slip by. With our 1/3 deposit down, we sat in limbo, year after year. Finally, the day came—we boarded our plane for the trip of a lifetime.

We started this adventure as a group of four, but with three years of change (especially with our sons), it became a trip for two. We flew direct from New York to Cape Town—and I’m happy to report, I actually slept like a baby!

Where We Stayed & Ate

We checked into More Quarters, a stylish boutique accommodation with fantastic staff and a great location. Just a couple of blocks away was Black Sheep, one of the restaurants on my must-try list. It did not disappoint—excellent food, unique sharing plates, and a casual, lively vibe.

Lion’s Head & Table Mountain

Our first big adventure was the trek up Lion’s Head. Originally, we planned to hike at sunset, but Rachel wisely suggested a morning climb for safety reasons. Crime had been on the rise post-Covid, and desperate times can create desperate people.

We set out at 9 AM—and I’m so glad we did! The weather was perfect, the crowds were minimal (thank you, shoulder season!), and the view was simply spectacular.

Next stop: Table Mountain. Now, you can hike up, but why would you when the cable car is this good? The tram does two full rotations as it climbs, which means every window is the best seat in the house. Once at the top, allow at least an hour to explore the viewpoints and trails.

Pro tip: only go when the weather is clear—social media updates are your best bet for conditions. And dress smart: layers, good shoes, and a water bottle. If the weather turns, the tram can close, forcing a walk down the mountain.

Bo Kaap - Malay Quarters - the first location I felt nervous of safety

Bo-Kaap – The Malay Quarter

Bo-Kaap was one of the places I most wanted to see, but it was also the first area where I felt uneasy about safety. Once known as the Malay Quarter, it’s now a famous Instagram stop thanks to its rainbow-colored houses.

Fun fact I learned: these homes were originally required to be painted white when leased. Once slaves were allowed to buy property, they painted them in bright colors to celebrate their freedom. A powerful, beautiful symbol.

Sadly, the area has changed, with tent cities and aggressive street activity. We only stayed briefly, ducking into a couple of artist shops. I regret not purchasing some of the recycled wall art I admired—I wouldn’t return alone.

Thankfully, our guide kept us safe, even through a tense situation as we returned to our car. Street smarts go a long way in Cape Town.

A Taste of Cape Town

To lift our spirits, we headed downtown for lunch and coffee. And not just any coffee—Truth Coffee, often ranked among the best coffee shops in the world.

Some of the other food location you could consider: The Electric (District 6) — a hip café with industrial loft vibes. Good choice for breakfast / lunch near Truth.

Swan Café — a French-style crêperie, charming décor and good for something lighter or lunch.

Belly of the Beast — small, creative, “fun fine dining” option on Harrington Street. Booking in advance is smart.

New York Bagels — an institution; family run, best bagels and cheesecake.

The Art of Duplicity — a speakeasy style spot (light eats) in the Buitenkant area (you’ll need to pre-book).

Harringtons — cocktail bar + food upstairs on Harrington Street. Good for an evening out.

If only we had more time - loved the food vibe here.

From there, we visited the Iziko Slave Lodge, one of the oldest buildings in the city. Its exhibits take you on a sobering journey “from human wrongs to human rights.” Walking through slave cells, wells, and relics was heavy, almost like visiting a concentration camp—the air felt still, almost sorrowful.

Nearby, we saw reminders of apartheid—benches still marked “White” and “Non-White,” and the Slave Bell that once controlled lives. Not far away stands a monument to Archbishop Desmond Tutu, Nobel Peace Prize winner and fierce human rights advocate.

His 14 symbolic wooden pillars represent the chapters of South Africa’s constitution.

Travel really is the best teacher.

Penguins, Gardens & The Cape

The next day was for the iconic sights outside the city: Boulder Beach, Cape of Good Hope, and Kirstenbosch Botanical Gardens.

Spring (August–November) is the most colorful time at Kirstenbosch, and being there in September was perfect. The fynbos was in full bloom!

Cape of Good Hope Tour

Boulder Beach was another highlight—home to the African penguin (also nicknamed the “Jackass penguin” because its call sounds like a donkey bray). Watching them waddle awkwardly on land before face-planting into the waves—only to transform into sleek, duck-like swimmers—was pure joy.

Dining Adventures

Of course, no trip is complete without dining experiences. Rachel gave us a fantastic restaurant list, and we started booking about three months ahead (good thing too—many spots were full).

One night in Camps Bay didn’t go as planned—the service was so poor we left after one drink, only to witness a street brawl while waiting for an Uber. Not quite the romantic sunset evening I had imagined—but definitely a story to tell!

A much better experience was at GOLD Restaurant—a 14-course tasting menu with live African music, face painting, and even a chance to dance.

Tip: book the earlier time slot with drumming and request a main-level table. It’s an unforgettable night.

Shopping & a Grand Finale

We set aside one shopping day at the V&A Waterfront. Pro tip for travelers: I always pack a foldable duffle (thank you, MEC!) so I can check extra purchases on the flight home. A stop at PostNet let us ship insured packages straight to our final hotel in Joburg.

To close out Cape Town, we dined at Signal at Cape Grace, a hotel often named among the best in the world. Everything was flawless—the décor, the flowers, the service, and the food. A true five-star finale to our time in the Mother City.

Cape Town - Mother City and our starting point to South Africa