I had envisioned sunshine on pastel Painted Ladies, effortless cable car rides up gentle hills, and days filled with tech-fueled wonders and artisanal coffees.
In my mind, the City by the Bay would be a soaring tech utopia with perfect California weather.
As a first-time visitor, I thought I knew what to expect. But from the moment I arrived, reality had other ideas. Nothing about my San Francisco trip went the way I planned, and it turned out to be a journey I’ll never forget.
Great Expectations, Foggy Reality
My fantasy of a balmy Californian welcome evaporated as soon as I stepped outside the airport.
Instead of golden sunshine, I was greeted by a chilly breeze and a haze of fog. It was June, and I’d foolishly packed mostly T-shirts and a light hoodie. Locals often joke that “the coldest winter I ever spent was a summer in San Francisco,” a saying popularly (if erroneously) attributed to Mark Twain. Now I understood why.
The famous fog, nicknamed “Karl” by residents, had rolled in thick. By the time I reached my hotel, my teeth were chattering. I remembered reading that the city’s weather can change by the hour and even from block to block, thanks to its microclimates.
Bring layers, the guide had warned. Yet here I was, shivering in June, scrambling to buy an “I ❤ SF” sweatshirt from a souvenir shop at Fisherman’s Wharf.
Despite the unseasonable cold, I was determined to dive into sightseeing. Day 1’s plan was to stroll along the Embarcadero to the Golden Gate Bridge, a gentle warm-up for the adventures ahead. But San Francisco’s terrain had other plans for me. I soon discovered that “flat” is not in this city’s vocabulary.
Every route I took seemed to end at the base of a towering hill. Streets I’d imagined as mild inclines turned out to be as steep as rollercoaster tracks. Huffing and puffing, I made my way up Nob Hill on foot, pausing every few minutes to catch my breath and marvel (or curse) at the 45-degree angles.
My calves burned, and my heart pounded. By the time I reached the top, any notion of a “gentle stroll” had vanished. San Francisco makes you earn its views.
Lost in the Urban Maze
The city’s geography and layout were an unpredictable maze. On a map, everything looked so close together – the 49 square miles of San Francisco deceive with their compactness. In reality, those miles are packed with winding streets and sudden changes in elevation.
My second day, I set out confidently with my phone’s map app to find a famous brunch spot. Twenty minutes later, I found myself completely lost in a tangle of one-way streets and hills, the skyline disappearing behind fog every few blocks. Eventually, I stumbled into a quiet residential street lined with Victorian houses painted in every color of the rainbow.
This wasn’t where I meant to be at all. Yet in that unplanned moment, panting from yet another ascent, I noticed something: a break in the mist revealing the Bay Bridge glittering in the distance, and the faint smell of fresh sourdough bread wafting from a nearby bakery. For a moment, being lost felt serendipitous.
Getting around the city proved to be an adventure in itself. I had envisioned zipping around on iconic cable cars and modern transit with ease. The reality? I spent my first bus ride frantically digging for exact change, having failed to purchase the all-important Clipper Card that locals use to navigate the patchwork of BART trains, Muni buses, streetcars, and cable cars.
One afternoon, I hopped on a historic cable car on Powell Street, determined to ride it to Lombard Street as I’d planned. But it was so packed with tourists that I clung precariously to the running board, the wind whipping my face as the car lurched over hills.
When I finally disembarked, I realized I’d overshot my stop by many blocks – the conductor’s announcements lost in the clamoring crowd. On another day, I descended into the BART station intending to visit the Mission District. Despite staring at the route map, I promptly boarded a train going the wrong direction.
I ended up in a part of the East Bay I’d never heard of, far from any itinerary, before I could switch back.
It was humbling. San Francisco’s transit had me utterly baffled at first, and I felt like a clueless outsider. (I eventually did get that Clipper Card, which made life a lot easier, but not before a few such misadventures.)
Encounters on Unplanned Paths
In straying from my plans, I also encountered sides of San Francisco I hadn’t anticipated. Walking back to my hotel near Union Square one evening, I took a wrong turn and found myself on a dimly lit block that felt worlds away from the polished storefronts a street over.
Here, people camped in doorways and tents lined the sidewalk. A man muttering to himself stumbled past, and on the corner a woman with a shopping cart was howling an incoherent song into the night. My heart rate quickened. This wasn’t the postcard San Francisco I’d imagined; it was raw and real.
I’d heard about the city’s homelessness crisis, but seeing it up close was jarring. The fact that San Francisco has a serious problem with homelessness is no secret – later I learned that an estimated 8,300 people were homeless in the city as of early 2024.
But statistics are one thing; the human reality is another. I felt a mix of compassion and unease as I navigated around makeshift encampments. That night, I lay in my comfortable hotel bed grappling with conflicting feelings.
I was grateful for my safety but troubled by the stark inequality I’d glimpsed. It wasn’t the experience I had planned, but it opened my eyes in a profound way.
Not all my unplanned encounters were so sobering. Some were delightfully quirky. On a crowded bus through Chinatown, I found myself squeezed in shoulder-to-shoulder with elderly Chinese grandmothers toting groceries.
The air was thick with the smell of fresh bok choy and whispers in Cantonese. At the next stop, nearly the entire bus emptied out (all the grandmas off to cook dinner, I imagined), leaving me chuckling and with plenty of elbow room.
On another day, while wandering through the Mission District after a detour, I stumbled on a vibrant street mural that wasn’t in any guidebook – a riot of color depicting community heroes and cultural history.
A local artist painting nearby nodded at me and smiled, as if to welcome me into this hidden corner of the city’s soul. Moments like these – completely unplanned – became the highlights of my trip.
And then there was the city’s vaunted tech culture, which I had expected to see everywhere in gleaming evidence. I pictured sidewalks filled with hoodie-wearing innovators riding e-scooters to sleek offices, maybe even robots delivering lattes. The truth was less flashy and more nuanced.
Yes, I saw plenty of people working on laptops in cafes, and I did spot a Google shuttle bus cruising through SoMa one morning. I even had a surprise run-in with the future: one night, a car rolled by with no driver in the front seat – one of those new autonomous taxis prowling the city.
Futuristic, yes, but also oddly eerie, gliding through streets where not far away people were sleeping rough. The juxtaposition of tech wealth and social struggle was impossible to ignore.
San Francisco is indeed a global tech hub, but on its streets you see a diversity of life beyond the tech bubble. In the end, the “tech culture” wasn’t a tourist attraction – it was part of the complex backdrop of the city, present but not overtly on display to an outsider like me in the way I had imagined.
Chasing Icons Through Mist and Change
Of course, I couldn’t leave San Francisco without paying homage to its most iconic sights – though even those didn’t go as planned. My carefully scheduled sunrise photo-op at Golden Gate Bridge?
It turned into a lesson in the supremacy of fog. I arrived at the Golden Gate Overlook in predawn darkness, expecting to watch the first light paint the famous orange towers. Instead, I found myself peering into a thick wall of gray.
Karl the Fog had decided to swallow the entire 1.7-mile span of the bridge that morning. As the sky lightened, I could barely make out one of the bridge’s towers before it vanished into a ghostly mist.
Disappointed, I started to walk onto the bridge anyway, bundled in every layer I had. The sound of the bridge was unforgettable – the eerie moan of fog horns blaring somewhere in the white void around me, and the distant cries of seagulls echoing off the bay. Moisture hung in the air, dewing on my eyelashes. I couldn’t see the Bay at all, let alone the city skyline.
This was not the postcard-perfect scene I had imagined. And yet, there was a strange beauty to it. Halfway across the span, shivering and wind-whipped, I laughed at the absurd magnificence of the experience.
Here I was, finally on the Golden Gate Bridge, but it felt like standing inside a cloud. When a brief gust cleared the fog for a few seconds, I caught a magical glimpse of sailboats below and the Marin Headlands in the distance before the mist closed in again. In that moment I realized: San Francisco was giving me the experience it wanted to give, not the one I had planned.
I adjusted my plans on the fly. Instead of the picturesque hike in the Marin Headlands I’d scheduled (called off due to that stubborn fog and an unexpected bus route change), I spent an impromptu afternoon warming up in the Ferry Building marketplace.
There, I sipped a decadent cup of hot chocolate from a local chocolatier while watching ferries come and go on the bay, the Bay Bridge now visible as the fog shifted. It wasn’t what I’d intended for that time, but it was cozy and comforting in its own way.
Later, when the sky cleared a bit, I made my way to Alamo Square to see the famous Painted Ladies – those elegantly colored Victorian houses. This, I thought, would surely go to plan. But fate intervened in the form of a film crew that had cordoned off the park.
I couldn’t sit on the grass for the classic view of the houses with the downtown skyline backdrop. Instead, I watched from a corner as the sun broke through at golden hour, illuminating the Painted Ladies just for a moment. I snapped a photo from my less-than-ideal vantage point and smiled. It was still beautiful, just... different.
Culinary Surprises and Detours
All my life I’d heard about San Francisco’s legendary food scene, and I had big plans to indulge: a reservation at a Michelin-starred restaurant, clam chowder in a sourdough bowl at Fisherman’s Wharf, and a pilgrimage to the Mission District for an authentic burrito.
Not all those plans panned out. The Michelin-starred dinner was scrapped when my sightseeing ran late after a delayed ferry (a bridge closure had caused chaos on transit). I ended up that night in a tiny family-run Italian joint in North Beach, sharing a table with two friendly strangers (fellow stranded would-be diners) because the place was so crowded.
Over plates of unexpectedly divine eggplant parmesan and glasses of red wine, we exchanged travel stories. It wasn’t the chic culinary experience I had reserved months in advance – it was something warmer, more spontaneous, and just as memorable.
The next day, I did make it to Fisherman’s Wharf, eager to try the famous sourdough chowder bowl. I found the Boudin Bakery, teeming with tourists, and finally cradled the hollowed-out round of sourdough filled with steaming clam chowder.
It was tasty, yes, but as I sat on a bench overlooking the marina, I found myself more drawn to the scene around me: sea lions barking on Pier 39 and a street performer juggling while balanced on a unicycle.
The chowder bread bowl had been on my must-do list, but it was the atmosphere of that unplanned street show and the ocean air that became the real treat.
My most delicious surprise came from a plan gone wrong. I had intended to have lunch at a trendy new restaurant in the Mission, but showing up without a reservation on a weekend was a rookie mistake – the wait was two hours.
Hungry and a bit dejected, I wandered down Mission Street until the smell of grilled carne asada and spices hit me. On a busy corner was a line of people outside a hole-in-the-wall taqueria. I figured why not join them. Ten minutes later I was biting into the biggest burrito I’d ever seen.
It was a classic Mission-style burrito, bursting with rice, beans, salsa, guacamole, and more. To my astonishment, it even had crispy tater tots tucked inside – a playful twist known as the California burrito. I hadn’t planned for this, but it was glorious.
Juice dripped down my hands as I devoured the flavorful, messy masterpiece on the sidewalk, vulturing a shared napkin with a laughing local next to me. That unplanned burrito blew my fancy restaurant plan out of the water.
Similarly, I stumbled upon a tiny bakery in Japantown where I tasted the most heavenly matcha cream puff after randomly following a sweet, toasty aroma down a side street. San Francisco’s food scene truly shone when I let go of the guidebook and went wherever my nose or whims took me.
Finding Meaning in the Unplanned
As my trip neared its end, I realized how transformative the unexpected had been. The city had humbled me, surprised me, at times even scared me – but it also taught me to embrace uncertainty.
Not once did my days unfold exactly as I’d drawn up on paper. And that was okay. In fact, that was wonderful. On my last evening, I walked out to Ocean Beach on a whim (another journey by bus where I almost missed my stop).
The Pacific wind was cold and fierce, and fog was gathering again, but the sound of crashing waves and the vast horizon at sunset gave me a moment to reflect. I thought about how I’d come seeking one version of San Francisco, only to meet another, more authentic one. A San Francisco that is messy and beautiful, frustrating and inspiring all at once.
My expectations had been upended at every turn: the weather, the hills, the encounters, the logistics, even my meal plans. I had been forced to live in the moment rather than in my itinerary, and in doing so, I discovered the real San Francisco – a place far richer and more complex than the postcards or Instagram feeds.
The city challenged my assumptions (sometimes harshly), but it also gifted me serendipitous joys: a kind stranger giving me directions in a confusing Muni station, a spontaneous conversation with an artist at a gallery I ducked into to escape the rain, the sight of the Golden Gate peeking through mist just when I’d given up hope, and the comfort of a good burrito after a long, hard day.
In the end, I left San Francisco not with the tidy album of perfect vacation photos I’d envisioned, but with something better: stories and reflections that felt genuine.
The trip that went “wrong” in all the right ways. On the flight home, gazing out the window as the plane ascended over the foggy Bay, I found myself already feeling fondness for the city that had so thoroughly derailed my plans.
In a way, San Francisco gave me exactly what I didn’t know I needed. I learned to roll with the punches, to find beauty in imperfection, and to appreciate a city for what it is, not what I imagined it to be.
Nothing about San Francisco went as planned, and that made it my own unique story to tell. I came for a dream, but I left with an experience, and a reminder that the best travel memories are often those we never could have scripted.