Do these things when you’re in San Francisco: spend a day at Dolores Park, watch sea lions at Pier 39, and get wasted on an old-school streetcar. What if you could rent that train, invite all the fun people you know, blast music and have a party?
You can, and we did.
If you’re a longtime follower of The Bold Italic, you may have heard we have new owners; they hired me as editor in chief several months back, and I sweetened the deal by saying I’d bring back quirky TBI events that capture the fun of San Francisco. What’s more San Francisco than an OG Rice-A-Roni Powell St. trolley?
That was my original thought, at least. Both cable and streetcars are available for charter with some caveats: only historic and vintage streetcars allow booze, food, and music. Many have limited seating, and you can’t bar hop — the train goes along a predetermined route with very few stops. SFMTA actually told me no stops at all when we emailed, but the operators kindly made a bathroom break; they also let a few riders off early and picked one up belatedly.
I picked the F Line for its 52-seat capacity. The charter cost $500 for two hours, and remaining ticket sale dollars went toward every ounce of booze I could pack. Rye on the Road supplied us amply with a paloma cocktail and gin gimlets, and everyone drank those so fast, with my hands grabbing ice and filling airplane cups with sippy lids for a solid 40 minutes as the train got going. My boss hustled around too — oops — filling cocktails from Rye on the Road, and making sure everyone signed the “don’t sue us” waiver.
Everyone really enjoyed the experience and there’s genuinely no downsides to tell you. The train rolled from the Castro, along Market Street and then up Embarcadero on an uncharacteristically nice summer day for 2023. Everyone got along — nothing super trashy happened, much as that would have been fun to report. Who could’ve predicted success when publicly inviting friends and strangers to get messy on a 2-hour train ride? But it’s an experience I’d do again in a heartbeat.
Photos below of our shenanigans, and follow us on Twitter, Instagram and Substack to find out about our next event.
Saul Sugarman is editor in chief of The Bold Italic.
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