San Francisco: The Trip That Didn’t Go According to Plan (And Why That Was Perfect)

Planning trips in advance can be one of the most satisfying parts of travel. There’s something powerful about mapping out the perfect route, timing golden hour down to the minute, stacking iconic landmarks in geographic efficiency, and knowing exactly where you’ll be when the light hits just right.

But what happens when things get in the way?

What happens when a thick blanket of fog erases your sunset? When traffic shifts your timeline just enough to make the ending impossible? Or when a conversation with a stranger becomes so enthralling that you lose track of time?

What if all of it happens on the same trip?

Are you stuck? Or do you lean in and come home with something even better than what you planned?

If you know me, you already know the answer. San Francisco became another beautiful reminder.

My plane landed fifteen minutes early at SFO, and I felt that familiar rush of momentum. I had built a fully optimized photo itinerary. Sunset at Crissy Field. Blue hour in North Beach. Chinatown after dark. The Ferry Building glowing beneath the Bay Bridge lights. It was tight. Efficient. Dialed in.

And then I stepped onto the curb outside the airport.

No sunshine.

Instead, thick low clouds and hazy wisps of fog wrapped the skyline like a heavy gray blanket. The kind of fog San Francisco is famous for—but not the kind photographers pray for when chasing fiery sunsets. I only had this one afternoon. The next two days were packed wall-to-wall with meetings. This was my window.

So I did what travelers do. I pushed on.

Randy, my 65-year-old locally grown cabbie, drove me up to Coit Tower while narrating how the city had evolved over his lifetime. We talked about neighborhoods, about tech, about how the city “used to feel different.” Eventually he asked what brought me in, and when I told him I was chasing the best photo views the city had to offer, he paused before throwing me my first curveball.

“Treasure Island,” he said confidently. “Best skyline view in the city.”

Treasure Island? Across the Bay Bridge? In this weather?

You can get stuck on that bridge for an hour if you’re unlucky. It felt risky. But I’ve always believed something simple: high risk often leads to high reward. I filed the idea away as I shot panoramas from Coit Tower—skyline compression shots, Alcatraz hovering in haze, the Bay Bridge dissolving into gray. The city felt moody and mysterious. Not what I planned. But interesting.

Next stop: the Palace of Fine Arts.

If Coit Tower gives you perspective, the Palace gives you poetry. Massive columns, intricate carvings, symmetry reflected perfectly in the lagoon. Engagement photos were happening on one side. A wedding shoot on the other. Life unfolding in front of timeless architecture.

As the afternoon light softened, I focused on the transition from brightness to shadow, from solid stone to fluid water. The fog filtered the sun just enough to create depth instead of drama. It wasn’t golden hour fireworks. It was subtle. And subtle has its own beauty.

Standing there, I made the call.

Treasure Island.

The drive out across the Bay Bridge wasn’t bad at all. Light congestion, but nothing alarming. The skyline slowly revealed itself as we crossed, buildings rising through layers of fog like something half-real. My Uber driver’s name was Rajesh, but on the way out we mostly rode in comfortable quiet. Just another ride. Just another stop.

He dropped me off and I went hunting for the angle.

The view from Treasure Island was moody and layered, fog drifting between buildings, the city textured instead of polished. It wasn’t the crystal-clear postcard skyline I had envisioned. It was more cinematic than that. I grabbed a handful of shots and ordered my next Uber to head back into the city so I could catch golden hour at Crissy Field.

And that’s when everything shifted.

Guess who pulled up.

Rajesh.

This time, as we merged back onto the bridge, traffic tightened. What had been smooth on the way out turned into steady congestion heading back into the city. Brake lights stretched endlessly in front of us. My carefully timed golden hour window started slipping away minute by minute.

We started talking.

About the bridge. About how unpredictable it can be. About how San Francisco light rarely does what you expect. And somewhere in that slow crawl across the Bay, photography entered the conversation.

It turns out Rajesh loves shooting the city as much as I do.

By the time we reached the city limits, golden hour had mostly dissolved. Blue hour was approaching faster than planned. The schedule I had optimized so carefully was no longer possible.

And that’s when the trip got better.

Instead of rushing to salvage the original timeline, Rajesh began mapping out a different plan. If we were going to miss golden light, we could chase night reflections. If traffic had shifted the rhythm, we could lean into it. He pointed out angles that work best after dark, secret overlooks that glow when the city lights come alive, streets that transform once headlights replace sunlight.

Rajesh didn’t just drive.

He curated.

He took me to quiet overlooks where the bridge framed perfectly between buildings. To streets where damp pavement reflected city lights like glass. To corners that would never show up in a standard “Top 10” list.

We compared shots. Adjusted framing. Watched the sky transition from muted dusk to deep indigo. The evening I had planned for golden warmth unfolded instead in cool neon and shimmering reflections. What I thought would be a sunset shoot became a night photography session I never would have engineered on my own.

Did I hit three-quarters of my original itinerary?

Not even close.

The congestion on the bridge had erased my golden hour window. The fog had muted the dramatic skyline I expected. The timeline I built never fully happened.

But what I gained instead was better.

We drifted through North Beach as café lights flickered on and conversations spilled onto sidewalks. Through Chinatown, where lanterns glowed against wet pavement and neon signs hummed to life. Toward hills where cable cars crested with headlights cutting through dusk. Down near the Ferry Building, where the Bay Bridge shimmered in quiet symmetry against the dark water.

It was colder than I expected. The fog never fully lifted. The city never gave me the blazing sunset I had designed my schedule around.

And yet it was unforgettable.

Because it wasn’t about the weather.

It was about the moment.

You should plan the perfect itinerary. Structure creates opportunity. But flexibility creates magic. If I had stubbornly clung to my timeline, I would have rushed conversations, ignored local insight, missed secret angles, and lost a potential friendship.

Instead, I gained a skyline I didn’t expect, perspectives I couldn’t Google, a new friend named Rajesh, and a story better than the one I planned.

Travel, like life, rewards those who pay attention.

So here’s my advice: talk to your Uber drivers. Ask questions. Listen closely. You never know when bridge traffic becomes a turning point. You never know when fog becomes atmosphere. You never know when a missed sunset becomes the best night of the trip.

San Francisco didn’t go according to plan.

It went better.