Over Memorial Day weekend, my boyfriend Cameron and I took our first trip out to San Francisco. I made an ambitious itinerary full of places to dine and day-drink, along with all of the inevitable sites to see, but a key item on the list was Don Herron’s Up and Down These Mean Streets. The tour has an illustrious reputation: For the past 37 years, Herron has donned a fedora and trenchcoat to walk visitors through Dashiell Hammett’s San Francisco.

My fandom was mostly based on the films Hammett inspired rather than his novels, but I was sure that could change. Visiting Berkeley, I dropped by Half-Price Books and picked up the cheapest copy of The Maltese Falcon I could find. I read the first few pages of Dashiell’s classic and tried to imagine myself in that kind of San Francisco.

Of course, the inevitable happened, the thing that always happens when you visit a place with the desire to do an explosion of things all at once: We couldn’t catch Herron’s tour. It fell on our last day in the city and last-minute things kept piling up — an old family friend was finally able to meet, there was a Carnaval parade in the Mission, and we still hadn’t seen the Sutro Baths.

Herron’s website firmly instructed that tourists allow four hours for the tour. That kind of time-frame begged for commitment. After surfing the internet and digging up a few locations, Cameron and I thought, hell, we’ll just do it ourselves.

We passed by The Westin St. Francis Hotel and admired its luxury from a distance. Fans of The Maltese Falcon believe this is the real-life equivalent of Dashiell's fictionalized St. Mark’s Hotel, where Brigid O’Shaughnessy first stays in the novel. We took our photos and caught a glimpse of its classic red awnings.

We hiked up Powell Street (quite literally), finally making it to Bush and Burritt Street, where a small alley houses a plaque that reads: “On approximately this spot Miles Archer, partner of Sam Spade, was done in by Brigid O’Shaughnessy.” Without Herron, this was our closest glimpse of where fact and fiction met.

On our first night in the city, before we had tried to tour Hammett's mean streets, Cameron and I had drinks at the Tonga Room & Hurricane Bar, afterward walking back to the Powell Street Station over the hills and through the fog. It was the San Francisco I imagined from Hammett’s stories, the San Francisco I’d see romanticized in pictures, one that lent itself irresistibly to the mystery and dark glamor of noir. The day we visited a few spots from Herron’s tour, it was just passed 11 A.M. and the sun was blinding. It was much too warm for a trench coat.

After just two landmarks from Herron’s tour, we took the MUNI Metro to catch the Carnaval parade. I wondered what it would have been like to see Hammett’s apartment and the other sites from the tour, if any of it would have given us a clearer view of old San Francisco. After the parade, Cameron and I saw an old family friend who hiked with us up to the Sutro Heights and took us down to the bath ruins, where the biggest salt water baths in the world once stood. We watched footage from 1897 of long-dead people slipping down water slides and stared out at the Pacific Ocean as it beat over the shore, the fog off in the distance, just waiting to come in.

After reading more of The Maltese Falcon on the plane back to New York, tourist’s remorse set in. Why didn’t we go on the tour? How could we have missed hanging out in the Tenderloin? Why couldn’t we just stay? (All signs of a good vacation, people will tell you.) I worried I had missed something larger by trying to see everything at once. Flying closer to New York, my East Coast neuroses came on: But what if Herron dies before you come back to San Francisco? What if you never actually get to go on the tour?

After some serious self-regulation, I told myself that we could always go again sometime and that when we finally did, San Francisco would bring its fog back.

Freddie Moore is a Brooklyn-based writer. Her full name is Winifred, and her writing has appeared in The Paris Review Daily and The Huffington Post. As a former cheesemonger, she’s a big-time foodie who knows her cheese. Follow her on Twitter: @moorefreddie

(Image credits: All courtesy of the author)

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