San Francisco: Last Days Before Heading South

Every city has a moment where it shifts from a place you’re visiting to a place you’re leaving. San Francisco hit that point on my second-to-last day. I still had places to go, things to see — but the energy had changed. Everything had that specific edge of knowing you’re about to move on.

Two days left before the Coast Starlight south to LA. Decided to spend them the way I’d spent the best days of the whole trip: walking, looking, eating, being present. No agenda. Just the city.

The City on Foot

San Francisco is a walking city, if you have the calves for it. The hills are not a metaphor or a charming feature — they are genuinely, absurdly steep, the kind of inclines that make you wonder who decided to build a city here. But the reward for every climb is a view that makes the burning in your thighs feel like a reasonable deal.

I wandered through North Beach, the old Italian neighborhood, where the smell of espresso and garlic hits you on every block. Walked the Embarcadero and watched the ferries come and go from the Ferry Building. Climbed Telegraph Hill — actually climbed it, stopping twice to breathe — and looked out at the bay, the bridge, Alcatraz sitting on its island in the water like a warning from history that the water decided to keep.

The Transamerica Pyramid seen from below against a blue sky
San Francisco in the afternoon. Every hill is a workout and every crest is a postcard.

The thing that kept surprising me about San Francisco is how many completely distinct neighborhoods exist in such a small geographic space. Seven miles by seven miles, and within that you’ve got the Castro, the Mission, North Beach, Chinatown, the Haight, Pacific Heights, the Tenderloin, SoMa — each one with its own personality, food, energy, history. It’s like someone took ten different cities and shuffled them into one grid. Chicago has neighborhoods but they blend. San Francisco’s neighborhoods have hard edges. You know when you’ve crossed into somewhere new.

I ate constantly. The Eat part of Eat Gay Love doing the work. Sourdough bread, which tastes different here than it does anywhere else — something about the fog and the local wild yeast cultures gives it a tang that you can’t really replicate. I know because I’ve tried. Seafood at Fisherman’s Wharf, which is touristy and I stand by it. Burritos in the Mission that were roughly the size and weight of a newborn, which I consumed standing at the counter feeling no shame at all.

Walked through Chinatown on a random afternoon and got completely turned around trying to find my way out, which is apparently a rite of passage. Found a bakery selling pork buns out of a window and ate two of them on the sidewalk. This is the correct approach to San Francisco.

One Last Night in the Castro

My last evening I went back to the Castro. It felt right. Walked the same streets I’d walked a few days earlier, but this time with the weight of departure on me — the rainbow crosswalks, the neon signs, the easy energy of people being themselves without apology. Wanted to soak it in one more time.

The Contemporary Jewish Museum at night, angular modern architecture lit up against the San Francisco skyline
San Francisco after dark. This city knows how to do nighttime.

Stayed out past midnight. San Francisco doesn’t shut down the way you might expect from a city that runs on tech money and cold brew — the Castro especially has a late-night pulse that keeps going. I sat outside somewhere with a drink and thought about what I’d done: the Empire Builder, the rainy week in Seattle, the Coast Starlight north, wine country, and now this impossible city built on hills and fog and defiance. It was, if I had to say, the best stretch of the trip so far.

San Francisco deserved more time. I was already planning when I’d be back before I’d even left.

Heading to Emeryville

The morning I left, packed my bag, checked out, and took the bus across the bay to Emeryville station. Same station where my stepbrother had picked me up when I arrived from Seattle. Different direction this time — southbound, the Coast Starlight continuing all the way down to LA.

Looked back at the skyline from the bus window. The city was half-wrapped in fog, the tops of the buildings poking through like they were wading in clouds. Familiar already. That’s how fast San Francisco works on you.

I’d be back. A city like this doesn’t let you go that easily.

But first: the California coast by train, and then Los Angeles.

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Michael Eisinger

Michael Eisinger

Program manager, nonprofit founder, and LGBTQ+ travel writer based in Silver Spring, MD. I’ve spent over a decade managing programs across nonprofit, healthcare, and medical education — and another decade finding out where the bears go. I write about travel that’s real, destinations that are genuinely queer-friendly, and the places that changed how I see things.

Filed under: Bear Travel