What happens when your first visit to a place goes wrong? T+L finds out on a rainy weekend in Cape Town.

Credit: Jason Fulford and Tamara Shopsin

I can’t tell you why it took me so long to get myself to Cape Town, a city with which I’ve been unfathomably obsessed since age 17, and I can’t say if things would’ve gone better had I not brought a quarter-century’s worth of expectations to our first encounter (I do tend to put a lot of stock in unseen places, and few held so much promise for me as this one). But I can tell you that my first encounter with Cape Town was quite frustrating. In fact, it outright sucked.

To understand how badly it sucked, you have to understand how much I was told it would not suck—how, in fact, seeing Cape Town would completely blow my mind, so drop-dead beautiful is it, so cool and cosmopolitan, with the music and the art and the mountain and the beaches and the waterfront and the Winelands and omigod Peter you’re going to LOVE it. No human in the past 20 years has uttered a less-than-exuberant word about Cape Town, at least nobody I ever met. It is the Radiohead of travel destinations.

The city had been lodged at the top of my life list for more than half my life, and although I travel for a living, somehow I never landed there. I suppose I held off for this long so I’d always have at least one great place to look forward to, one fail-safe option in my pocket. And Cape Town seemed as close as anyplace to being a sure thing. No way would I not fall in love with it.

Well. Last fall I finally made it to Cape Town, and things went south from the get-go. First of all, it rained nonstop: cold, harsh, bitter-making rain. The entire city was shrouded in mist—not the atmospheric mist of Tolkien or Japanese landscape paintings but the gloomy miasma of a sub-Antarctic squall. My hotel room ostensibly had a view of Table Mountain—I’d seen pictures on the website—yet for three days and nights I could barely see past the window, so thick was the fog and so heavy the downpours. I ventured out to get a closer look, sloshing up Kloof Street in leaky shoes and soaked socks, but wherever I went, a great black cloud loomed where the mountain should’ve been. The verdant hills, the sparkling sea, the gracious skyline were cloaked in murky sheets of rain. I might as well have flown to Worcester, Massachusetts. (At check-in, the receptionist had told me that Cape Town weather changes constantly, “like a teenager’s mood swings,” but this particular teenager managed to sneer at me for the duration of my visit.)

On top of the weather, I had arrived in the middle of a holiday weekend, when pretty much everything on my to-do list—the District 6 Museum, the galleries of Woodstock, most of the good restaurants—was shuttered and dark. With hardly anyone on the street, this so-called vibrant cosmopolis felt like a ghost town, all pulled-down grates and padlocked gates.

Dismayed yet determined, I pushed on. I’d waited 25 years to see Cape Town—would I be thwarted by some measly @#$%ing clouds? I would not! I would trudge my way up to Bo Kaap, the Cape Malay quarter whose famous pastel façades appeared decidedly less vibrant than in photographs. I would squish-squosh around the waterfront, imagining how much better it might look with actual people on it. I would comb the side streets and back alleys, searching for anyplace that was open and dry: the odd hipster café (YoursTruly, on Long Street), vintage vinyl shop (Revolution Records, a trove of Afrobeat in the Observatory District), or reflexology spa (Happy Feet, a cheap spot downtown). I would even hike to the muddy summit of Signal Hill, high above the city, to gaze out upon…a damp wall of unredeeming gray.

I would almost convince myself I was enjoying this. Was it really that bad? I was here, at last, in this long-dreamt-of city. For that fact alone I felt blessed. As for cruddy weather and rotten timing, I’d experienced plenty of both in other places—enough to know it needn’t spoil a trip. Rainy days and Sundays never get me down in London, a city that knows no “off” days; Waterloo Bridge looks as regal in fog as it does in clear sunlight, arguably more so. Tokyo overflows with life at all hours, holidays included. New York’s sidewalks are never entirely empty, even during a hurricane.

Yet there was something eerie about Cape Town on this rain-lashed holiday weekend: like a phantom city, it had virtually disappeared. Had I missed some tsunami or typhoon warning? News of an impending zombie attack? No, no, sir! the hotel concierge assured me. It’s just the time of year, plus the bank holiday, of course, and these nasty storms don’t help at all. But it truly is a lovely city, sir! You must return in summer, when it really comes to life.

This didn’t lift my mood. Even worse than rueing your own misfortune is realizing that it’s your fault—that if you’d just come in the proper season or on the right day of the week you’d be enjoying the city at its most resplendent. It wasn’t the place that failed you, in short; it was you who failed the place.

The upshot is that I spent three straight days feeling bad for myself, feeling bad about Cape Town, and feeling bad about feeling bad about Cape Town. I was a one-man feedback loop of woe, disappointed by my own disappointment, stranded on the Cape of Dashed Hopes.

By Tuesday morning I’d had enough of traipsing around in soggy loafers, so I rented a car and beat a hasty retreat to the Winelands. A few days at an inn in Franschhoek raised my spirits. At the end of the week, the sun miraculously returned to a clear blue sky just as I pulled back into Cape Town, this time on a sparkling Friday morning—and the city looked absolutely stunning. It was as if I’d stepped out to the theater lobby for intermission, then returned to find a whole new set onstage. I could see the mountain, I could see the ocean, I could see chic Capetonians in the parks and at sidewalk cafés; I could finally see what everyone has been raving about all this time.

It suddenly hit me that I was flying home in two days, so I spent the next 43 hours rushing around in a state of elated panic. I walked among beds of Namaqualand daisies at the Kirstenbosch National Botanical Garden. On a springlike Saturday I joined the bearded bread-makers and hipster charcutiers at the Neighbourgoods Market, where salvaged doors topped with gingham serve as communal tables for a few hundred like-minded food lovers. I made my way back to Bo Kaap, whose rose and marigold façades now shimmered brightly in the noonday sun. I discovered lavender-scented De Waterkant Village, which hits all the marks of gentrification: Vespas, French bulldogs, a Kartell emporium. (Very “vibey,” as South Africans say.) I browsed the funky design shops of Loop Street, then caught a cab to the Twelve Apostles hotel, just 15 minutes over the mountain, in time for sundowners above a golden, shimmering Atlantic. Ohh, I said to myself. NOW I get it.

I’m not sure what I could have done to make that first waterlogged weekend less frustrating. (Rescheduling my trip to January—South Africa’s high summer—might have helped.) But I do know this: even in perfect conditions, there was no way Cape Town could have lived up to my lifelong expectations. No place could. In some sense that unhappy first visit was sort of my fault: I’d no right to build the city up to that impossible standard—and no right to feel so crushed when it didn’t fully deliver.

Yet this is precisely what we do as travelers: we maximize anticipation. We believe the hype, then double down on it. We romanticize places beyond all logic, thinking we’ll be better, happier people there. We gaze upon too many sun-drenched photographs of our fantasy destination, until we’re convinced it never gets cloudy and summer lasts all year.

Lofty expectations, however, are not really the issue—in fact, they’re kind of the point. (Without them, who’d consider a 16-hour flight?) The trick is adjusting your expectations after you’ve arrived. On a big-ticket trip, acknowledging disappointment is akin to admitting defeat. Even a hint of disenchantment can seem like a personal failing. Everyone said this would be amazing…so what’s wrong with me that I don’t feel it, too? Moving past disappointment takes genuine patience and skill; it may be the hardest task a traveler has.

Ultimately, seeing Cape Town at its least flattering made for a truer, more intimate experience, albeit a maddening one at the time. On a gloomy Sunday when nearly everything was closed, I was forced to find other ways into the city, and wound up digging deeper than I might have otherwise. I had to earn the encounter, not merely show up for it. If and when I do return to Cape Town—and I certainly intend to—I actually hope it rains for a spell. A bit of drizzle would make me nostalgic. You never forget your first time.

Peter Jon Lindberg is Travel + Leisure’s editor-at-large.