theMilesWeKeep

From Family Wedding to Solo Roads: A Day and a Half in Cape Town That Left Me Wanting More

February 9, 2026

South Africa began as a family trip—rooted in love, celebration, and the kind of moments that remind you why gathering people from all corners of life matters. A wedding has a way of grounding you like that. It slows time, centers you, and fills your cup in ways that feel both joyful and emotional all at once.

And then… it ended.

As the family portion of the trip wrapped, I felt that familiar transition point—the shift from shared schedules and group energy back into myself. Over the last year, I’ve learned that this is where solo travel fits me best: not instead of family time, but after it. As a way to process, explore, and move at my own pace.

So when the wedding festivities concluded, I didn’t head home just yet. I flew from Port Elizabeth to Cape Town for a brief—but ambitious—solo chapter: a day and a half to get a true taste of one of the world’s most spectacular cities.

I landed in Cape Town that morning, picked up a rental car, and wasted no time. No hotel pause. No easing in. I headed straight down the eastern coastline, choosing momentum over comfort.

Driving through Fish Hoek, the scenery softened—quiet neighborhoods, calm water, an almost peaceful introduction before the drama that Cape Town is famous for. From there, I continued into the national park to see the penguins. Seeing African penguins up close on a beach, living their best lives, was one of those moments that feels oddly grounding.

I kept going south to Cape of Good Hope, where the land sharpens and the wind reminds you how powerful this place really is. Standing there, you feel small in the best possible way—humbled, present, awake.

From the Cape, I looped north along Chapman’s Peak Drive, a cliff-hugging road that feels like the U.S. Route 1… if Route 1 decided to be a little unhinged.

It’s breathtaking. And demanding.

Somewhere along those cliffs—right as confidence was peaking—Cape Town delivered its reminder: a flat tire, on the side of the road, with nothing but ocean below.

Not ideal. Slightly terrifying. Deeply character-building.

I handled it, stayed calm, and eventually got back on the road—making a mental note that this was definitely a story to share with my family after I was safely back on U.S. soil. Solo travel has a way of testing you just enough to prove you’re capable.

The payoff came at sunset in Camps Bay. Golden light, palm-lined beach, mountains glowing behind the water. After the day I’d had, it felt earned. Dinner followed before an early night because the next morning had one non-negotiable plan.

The next morning began with a hike up Table Mountain. Challenging enough to feel accomplished, rewarding enough to stop you mid-climb just to stare.

At the top, I lingered. The views stretch endlessly—city, ocean, mountains all competing for attention. I took the cable car down, legs grateful, heart full.

From there, I wandered through the vibrant streets of Bo-Kaap, soaking in the color and history that make the neighborhood feel alive.

Even on a solo adventure, work found its way in—in the best possible form. I snuck in a working lunch with one of our employer partners at the V&A Waterfront, a reminder that meaningful conversations don’t pause just because you’re traveling.

I ended my Cape Town sprint exactly how it deserved to end: at Beau Constantia. Rolling hills, thoughtful pours, and a moment to reflect on just how much I’d experienced in such a short window.

From the winery, I headed straight to Cape Town International Airport for a direct flight home—trading vineyards for runways, Africa for the familiar.

It was only a day and a half, but Cape Town delivered everything: coastline and cliffs, penguins and peaks, challenge and calm. It was the perfect bridge between family celebration and solo reflection—and just enough to make one thing very clear:

This wasn’t a goodbye. It was a preview.