All PostSouth Africa Women’s Trip Recap | Part 1: The Women
Just back from South Africa and still processing how good this one was.
Eight women. Three US states. Ages 58 to 82. Some knew each other, some had never met. All of them showed up open, game, and ready — and what unfolded over 10 days was one of those trips I’ll be talking about for years.
I want to share this in two parts — first the women and what happened between us, then the places, the wine, and the wildlife. Because honestly, the women always are the trip. The destination is the backdrop.
The Travelers
I knew everyone coming in — they came from different corners of my personal and professional life, some from prior Wonder Well trips, some from local women’s travel meetups I’ve hosted where they’d already become friends, a few who knew each other through work. Three were married, the others divorced or widowed. Some retired, some still working full-time at places like Microsoft and Bank of America. Most from the Philadelphia area, one from outside DC, one from Houston.
One thing I find consistently remarkable on these Wonder Well Travel small-group women’s trips is how quickly women connect across very different life paths. When we got together for dinner that first night in Cape Town, there was no formal kickoff, no orientation, no “go around and introduce yourselves.” I had sent brief bios by email before we left, and once we landed the getting-to-know-each-other just unfolded naturally, the way it does in any good social setting. By the end of the trip, someone observed that it had all happened so organically — and that that was perfect.
The first day or two was the natural conversations — where you’re from, what brought you here, any nerves about the trip. Someone admitted she almost didn’t come. Someone else said she’d never traveled with women she didn’t already know well. By mid-trip those early exchanges had given way to something much deeper — real conversations about losses due to divorce, death, and work transitions; what it feels like to reclaim independence after loss; men and dating after 55; what they wished they’d done sooner and what they want to do next.
Those discussions reminded me of a conversation I find myself having on every trip: I design these experiences not as a retreat, not as a workshop, not as a structured program to work through life challenges. Just a genuinely fun trip to a wondrous place — a chance to step away from the things dragging you down, or even just the everyday routine, and in doing so, with a group of women both similar and different from you, something quietly life-changing happens. You come home happier, stronger, more confident, and more yourself. Not because we scheduled it. Because travel — the right kind, with the right people — just does that.
The walls come down fast when you’re navigating a new city together, sharing a meal you didn’t expect to love, finding yourself halfway up a cliff in a strong coastal wind with nowhere to go but forward — or coming almost face to face with a female lioness in the dark, with nothing between us and her but the calm reassurance of our expert guide.
One Woman’s Triumph
Speaking of cliffs.
One woman in our group has been working through a fear of heights that developed after losing her husband — a real, physical anxiety response: panic on staircases, freezing on bridges. On a previous trip she needed two people flanking her to cross a hanging bridge with her eyes closed. On another she froze coming down from a rooftop restaurant in Greece.
This trip included a hike along the cliffs at the Cape of Good Hope — a narrow path and boardwalk, a strong coastal wind, and the cliff edge close. Honestly, it was a little unnerving for all of us. The wind was strong enough that at points we ducked down just to feel more grounded.
She started the hike fine on the dirt path, her close friend walking beside her. Then the boardwalk narrowed, the wind picked up, and the cliff’s edge came into view. Her anxiety rose.
She didn’t freeze.
She told us afterward she had been working on overcoming the fear for months before the trip. She also said something we all agreed with: once we’d come as far as we had, turning back wasn’t any easier than going forward — so we may as well power through. Pure pragmatism in the face of fear.
Then came the boulders — a scramble up and over large uneven rocks, manageable for her going up, genuinely nerve-wracking on the descent. Her anxiety peaked again coming down. Her friend stayed close. A few of us fell in around her. And then our guide — strong, calm, and yes, good-looking — came up from below to meet her and walk her down the last section.
She made it. All the way down.
We cheered. Loudly. She beamed.
That moment — unscripted, unplanned, completely earned — is everything I want these trips to be. Not the cliff, not even South Africa. The fact that she came, that she pushed herself, that the group showed up for her without being asked, and that she completed the hike successfully and proudly.
The Friends Who Joined Us
One more thing that made this trip special: two South African friends — a mother and daughter who have joined Wonder Well trips before — came to meet us on our first full day in Cape Town. They joined us for dinner, stayed at our hotel, had breakfast with us the next morning, and spent quality time with us sharing their love of their country — local tips, favorite spots, perspectives we never would have gotten from a guidebook. They were both so lovely and personable, and the warmth they brought into the group from day one set the tone for everything that followed.
We clicked. All of us. Immediately. Which, I’m grateful to say, has been the case on virtually all of my small-group women’s trips.
Every single woman on this trip said the same thing at the end: we came home with friends for life.
More on the itinerary, the Winelands, the penguins, and those unforgettable safari moments in Part 2 — coming soon.If any of this resonates and you’ve been wondering whether a trip like this might be for you, my DMs are always open. Our next Wonder Well Travel South Africa women’s trip is in the works. Send me a request at https://wonderwelltravel.com/contact-us/and let’s talk.
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Lori Zelko
Founder, Wonder Well Travel
Curated trips for women & beyond
