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PubClub Travel Adventures: Our Funny San Francisco Travel Misadventures

August 3, 2026 by kevinwilkerson Leave a Comment

Wrong Turns, Cable Car Mistakes, Missing Wine in Napa and Other Travel Blunders In The City By The Bay

Ashley & Kev's travel adventures San Francisco Lombard Street
Exhausted from our climb up Hyde Street, Ashley & Kev enjoy Lombard Street. Photo: PubClub.com

Not every trip goes according to plan. This one certainly did not between navigating San Francisco, missing signature cocktails and somehow visiting Napa without actually drinking much wine. But in the end, our mistakes became our biggest memories.

By Kevin Wilkerson, Editor of PubClub.com

Part of the PubClub Travel Adventures series, following firsthand journeys to nightlife destinations and unforgettable experiences around the world.

We were continually headed in the wrong direction, walked up a 40% grade street instead of taking a cable car and somehow wound up in downtown Napa and didn’t drink any wine.

This is the story of the misadventures of myself, Kev, and PubClubette Ashley as we sometimes stumbled our way through a weekend in San Francisco.

To be sure, we had some major scores, too, not the least of which was a room at the San Francisco Hilton Union Square with a sensational view of the bay and drinks at its rooftop Citiscape lounge. We also found a lively Friday afternoon bar for cheap drinks and good food, went to Alcatraz Island, had Irish coffee drinks at the famous Buena Vista, rode a cable car and walked up and down Lombard Street.

But those were our good travel adventures in San Francisco, which you can read in Ashley & Kev’s travel adventures, a separate post. This is about our mis-adventures in San Francisco.

Much of it involved navigation. Mine was off a bit, because it had been too long since I had been to San Francisco. I was convinced we should head off in one direction, only to realize we were going in the opposite direction.

Ashley, being younger and hipper than me (translation: she uses apps while I prefer to figure things out on my own) quickly realized Google maps would be better than relying on my “expertise,” but even that strategy failed us on occasion. “Hey, it showed we were 15 minutes from our hotel and now it shows 20 minutes,” she said on one occasion. “We’re headed in the wrong direction!”

When even Google maps can’t figure out which way to go, you know you’ve got a confusing city for getting your bearings.

PubClub.com travel blogger San Francisco street
Okay Ashley, I give up – which way back to the hotel!? Photo: PubClubette Ashley for PubClub.com

Part of the problem is the fact that San Francisco is on a peninsula. So, unlike just about any other place, you can’t use some obvious landmark like the water as a reference point because the water is all around you. Plus, all those downtown skyscrapers hide any other visuals; I had trouble locating Union Square even though we were often just a block or two from it.

Also working against us was the fact that we typically run into obstacles beyond our control when we travel. We once flew on a friend’s private plane to Catalina Island specifically to get its signature buffalo burger and Buffalo Milk cocktail. The day we went, the grill was broken (figures!) and we learned the Airport in the Sky no longer serves Buffalo Milks.

Fortunately, we both have good travel attitudes and let these little obstacles roll off our shoulders when things don’t go our way. Or, as Ashley says, “when life gives you lemons … drink champagne!”

Speaking of drinks, since Ashley was denied her signature drink on Catalina, I was eager to get her the signature drink of San Francisco. It’s the Cable Car cocktail and a few years ago, I made a trip to San Francisco specifically to research the bars that serve the signature Cable Car cocktail.

San Fransisco Cable Car Cocktail Johns Grill
The signature drink of San Francisco, the Cable Car Cocktail, as served (at least at one time) at John’s Grill in Union Square.

So I took her to John’s Grill which had the best one in the city. After we sat down, the bartender told me he never heard of it. A manager – who was not nearly as friendly as the one I encountered on my previous visit – looked at me like I was crazy and declared “we’ve NEVER had a Cable Car cocktail.”

“But I had it right HERE,” I protested as I pulled up the PubClub article and showed her a picture of two drinks at that exact spot on the bar.

That did little to impress her and, quite frankly, neither Ashley nor myself was really surprised.

I also had a plan for a cable car ride and while we eventually did get on one of San Francisco’s iconic trolleys, we blundered there, too.

San Francisco cable cars Hyde Street turnaround PubClubette Ashley
PubClubette Ashley at the Hyde Street cable car turnaround. Photo: PubClub.com
Hyde Street one of San Francisco's biggest hills
You can see me (blue shirt on sidewalk) trudging up Hyde Street, one of the steepest hills in San Francisco. Photo: PubClubette Ashley for PubClub.com

My plan was to jump on one at the Hyde Street turnaround and take it up that huge hill to the curvy part of Lombard Street. From there, we would take it back to the Hilton. This plan quickly unraveled as the line at the cable car turnaround was so long we would have had to wait close to an hour to catch it. As we were running short on time to join the rest of our group, we hiked up the hill. Let me tell you, that was like hiking up the Swiss Alps. With no switch-backs.

Later, after our Lombard Street experience (recommended for any first-time visitor, by the way, and while I’m on the subject, it’s far better to walk it rather than drive down it), we walked a few more blocks on Hyde Street and hopped on a cable car.

After Ashley was told to “get back” while she steeped into the driver’s compartment to take a video, we disembarked to catch another car to get to the Hilton. Naturally, we took off in the wrong direction and I later realized had we just stayed on that cable car we would have wound up back at the hotel.

Ashley & Kev's travel adventures San Francisco downtown Napa
Denied wine in Napa, Ashley and Kev have a travel misadventure. Photo: PubClub.com

The next day, we boarded a Tower Tours bus to Sonama and Napa Valley. We were part of a press tour group and as such, didn’t get to choose the tour. It certainly started nicely enough, a champagne and wine cheese pairing at the Gloria Ferrer winery.

We then spent 90 minutes drinking not wine but olive oil at a local producer and when we got to Napa, we went into a chocolate store for an hour rather than into several wine tasting rooms. We then left Napa and went back to San Francisco.

Granted, Tower Tours does have wine tours of Napa and Somoma but here we were, left high and dry in one of the world’s best wine regions with no wine.

As compensation, we did end our trip back up at Citiscape and then with great rum drinks at Smugger’s Cove, a somewhat hidden and locally famous downtown tiki bar.

We certainly managed to overcome our minor San Francisco travel misadventures and had a great trip to the City by the Bay. Most importantly, we were able to laugh about it during the trip, as well as afterward.

Now Hop On The San Francisco Party Bus To…

• San Francisco City Guide

• San Francisco Neighborhood Guide

• Bay to Breakers

• San Francisco: The One Line Single Peole Need To Know

Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and nightlife for more than two decades. While working as a newspaper reporter, he received an Associated Press award for investigative journalism.

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Filed Under: Blogger Tagged With: Ashley & Kev's Travel Misadventures in San Francisco, PubClub Travel Adventures, San Francisco Travel Misadventures, travel bloggers, travel blunders

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