I knew the look: slumped shoulders, crossed arms, glazed eyes. It was the teenage expression of tortured captivity, most often reserved for roadside attractions, railroad museums, and family reunion slide shows. Now the look was directed at me.

It was like that all day. My only response was to try harder.

I gathered the four blond heads of my cousins around a salon-style montage of art bulging from the SFMOMA’s wall like some sort of counterculture potbelly. “This,” I said while making an elaborate Vanna White gesture, “is Barry McGee.”

Four sets of blue eyes blinked blankly. The significance of Mission School Art was apparently not of interest to the 13- to 19-year-old Midwestern tourist subset. What was of interest? Fisherman’s Wharf, Ghirardelli Square, Chinatown—all the things my relatives had eagerly indulged in during the hours not spent at my brother’s wedding.

It was the San Francisco of snow globes and Rice-A-Roni boxes. It was not the San Francisco people lived in and certainly not the San Francisco of their 27-year-old hipster cousin—me.

So when a moody El Niño storm rained out their plans to zoom around town in those $50-an-hour go-carts, I seized the moment. We, I declared under a huddle of umbrellas, would engage in quintessentially San Francisco activities. Food, art, eccentricity—my cousins would see the side of SF most tourists only experience in passing.

I herded us over to SFMOMA’s 75th anniversary show. Amid the checkered scarves and asymmetrical haircuts of Bay Area art-goers, my cousins stood out, heads shining with the blond gleam of dairy farms and breweries. They wandered behind me as I excitedly pointed out notable works.

“Look,” I said, grabbing Katherine’s arm. “That’s a Jackson Pollock. You’ve heard of him, right?”

“Um, yeah, I think so.”

I poked Olivia. “Calder! He’s fun, right?”—met with a polite and somewhat pitying smile.

Thirty minutes of that was about all any of us could take. Slightly defeated but still clinging to hope—and the promise of an invigorating caffeine buzz—we tromped three flights of stairs and assumed a place in a line 20 people deep.

“Blue Bottle Coffee,” I explained, “is some of the best coffee in San Francisco. They’re part of this whole ‘third wave’ coffee craze, though, actually, the term is somewhat of a misnomer.”

At the front of the line, I asked for four mochas with whipped cream. The barista sneered, “We don’t have whipped cream,” as though I’d asked for ranch dressing at Michael Mina.

“Sorry guys,” I said, handing off cups with leaf designs swirled into their foam. “No whipped cream. But check out the foam.”

They sipped and nodded vaguely. “Oh!” Olivia’s eyes brightened. “Do you think the weather’s good enough to go to the Japanese Tea Gardens?” My heart sank.

“The tea there is kind of bad,” I began and then stopped. I realized suddenly that perhaps quality and contemporary relevance weren’t what they, and most tourists, were looking for. I felt the seize of the old travel writer debate: tourist versus traveler. It was one I’d always avoided—it sounded obnoxious and self-righteous to me. Now it was starting to make more sense.

Back on the sidewalk, in front of SFMOMA, the sun burst through the storm for a glistening moment of blue-sky crispness. The crowds milled about. Poking up above the bobbing heads, I spotted a black sign with neon block letters next to the angry twist of a face belonging to none other than Frank Chu.

I jabbed everyone in succession. “That dude,” I pointed out, not bothering to whisper, “is a Bay Area legend. He’s on some crazed conspiracy shit and protests everywhere. He shows up at every event. He’s more of a man about town.”

My cousins watched Chu as he uneventfully shuffled off. “So what does he do?” Kathryn asked.

“Um, well, nothing really. He just stands there. He’ll tell you all about his theory, if you ask,” I said, though I had to admit it was pretty anticlimactic. “Maybe it’s one of those things you have to see all the time to really get.” It occurred to me that maybe that was the answer to the debate and to why my cousins weren’t more excited about all the insider things I was showing them. It takes time for contemporary culture to be appreciated from the outside.

Andrew watched as a bus heaved past. “Hey, how would I get to Haight Street from here?”

“Haight Street?” I scoffed. “I can tell you how to get there, but I really don’t think it’s going to be what you have in mind.”

“Well, I don’t know.” He looked at his feet and leaned forward. “I mean, do you know of anywhere else to buy weed?”

I sighed. “No, I don’t. But I can tell you that Haight Street is probably about the worst place in the city to buy drugs.”

“But do you think I could? Even if, you know, it wasn’t good stuff.” I shook my head. Maybe it was true—tourists only come for the dead things, like the tie-dyed hippie days of the Haight, the relics of bygone culture that can be easily encapsulated and understood.

We took a moment to regroup and plot our next move. I bought a taco from Seoul on Wheels and passed it around. I didn’t bother to explain the cross-cultural significance of Korean barbecue tacos, high-end street food, and how years from now, my cousins might be lining up for this instead of bread bowls of clam chowder. “So,” Olivia said, chewing thoughtfully, “it’s like a fancy taco.”

I nodded. “Pretty much.”

Beside us, perched under a tree, Zach Houston set up his Poem Store, exchanging rhymes spontaneously written on his manual typewriter for pocket change. He eyed my group and gave his usual pitch: “Need a poem written?”

My cousins looked over at me. I smiled. “Now this will be a true San Francisco souvenir.” We fished together a couple dollars, and as Houston pounded the keys and chitchatted amicably, I didn’t attempt to explain the sociocultural import of San Francisco poetry. In the soggy sunshine, amid the hordes of art-goers, it pretty much spoke for itself.

Lauren Quinn’s blog is lonelygirltravels.com. She also blogs for The Huffington Post.