Goodbye SF Crawl
When I first moved to SF after graduating college in 2019, I had subletted a room from the brother of one of my friends from college in the Richmond District for the first 6 months being there. There was a random Sunday in early August of 2019 when I decided to pack my backpack & go on an adventure for the day. This wasn’t unusual for me. I had interned in SF for a summer in college & only had enough money for rent & groceries, so I got used to exploring through walks as something to do for free. You can essentially urban hike around the entire city. One day, I even walked all the way to Sausalito.
So that Sunday, I did just that. I walked from The Richmond, through the Presidio, Pac Heights, The Marina, Russian Hill, then I landed in North Beach. At this point, I wanted to grab some food & a little Aperol Spritz to treat myself. I stopped at this random bar, closer to the wharf. Knowing this area the way I do now, I don’t think I have ever landed back at this place, but this Sunday that is what I chose. It was pretty empty at ~1pm when I got there. I was in workout clothes & had my backpack with me. I sat at the bar. I have always felt comfortable sitting at a bar alone having a drink or food. I had been in the service industry from 16-22 & had bartended for a couple of years there too... so I just feel like I get it when I’m at the bar.
There were two other guys at the bar. They were strangers but had clearly formed a bond over the baseball games that were on that day. I minded my own business, ate my food, drank my Aperol Spritz, & then closed out & was going to continue on or go home. As I was about to leave, the guy next to me said something that kicked off a conversation. He then offered to get me an Aperol Spritz… I had a six-figure job out of college so I wasn’t strapped at this point, but I also was only two months out of college, so I still had that mindset of “I won’t say no to a free drink”. So we continued chatting & it turned out he was in tech too. He was on the sales side & most people in tech who were non-technical were always surprised to find out I was a software engineer, because there is definitely a certain archetype of software engineers in the Bay & I really don't fit it.
He had been an early employee at one of the bigger tech companies so he had some stories. He was at least 10 years older than me & had lived in Russian Hill most of his time in SF. I had told him how I just moved there & that I was figuring out where I wanted to live longer term after subletting. He said he was actually leaving SF in a month or two to move to San Diego. He offered to show me some of his favorite places since he knew the area so well & was about to leave. I was like fuck it. So this Sunday turned into quite the adventure.
Fast forward to 11 hours later & I found myself in this bar in Haight-Ashbury, still in my workout clothes & with my backpack, sitting with some comedians & watching this guy do an open mic comedy set. I was like “what in the actual fuck was this Sunday?”
We had gone to Blind Pig in the Marina for a cocktail on their patio. This then led to going to Devil’s Acre in North Beach where he knew the bartenders. We then were in Cow Hollow playing beer pong in the basement of a bar with random people. This guy was then an investor in a restaurant in North Beach, so we ended up there for dinner. We walked in & all of a sudden we sat down & he had aux over the whole restaurant. Then we proceeded to try over half the menu.
I saw him a couple of times after that before he moved & he continued to show me more places in SF. He invited me to an Oakland A’s game, back when they still had their stadium in Oakland, because he was throwing the opening pitch for the game. Every time he texted me, I was like “who is this motherfucker”. It sounds like this could have been romantic… but I assure you it was completely platonic & just a funny fucking dynamic.
As I was leaving SF, my friends proposed that we do a bar crawl in the city as our last hurrah before I leave & I thought about this day & him showing me his spots before he was leaving. I thought “okay what would I want to show people or do as I’m leaving??”
So I constructed this bar crawl in a very Connor fashion. I am kind of a fucking nerd about SF history. If anyone would walk through North Beach with me, they would get a random story or fact thrown their way. I also love leaning into the culture of a city that I am in. What do I need to eat or drink there that is infamous or historical? I wanted this bar crawl to tell a story. I would take someone who has never been to SF before on this tour & they would feel like they got to know me, got to know the city, got to know the food & drink culture, got to see views along the way. All of these things factor into the route.
There needed to be some sort of anchor & theme though. So the base was “drinks that are specific to SF”. They have a history linked back to San Francisco. They are heavily consumed in this specific geographical location. When you come to SF, people immediately say you have to get one of these drinks. That was the criteria.
My guidelines for the crawl:
“The whole basis is around famous SF drinks & the place (or group of places) we could get them at. Each stop is a cluster… some clusters have more than one bar, but those are just options for getting the same drink, not extra stops.
Not everyone needs to order these drinks at every place, but we do need to get at least one for the group to try together at each stop!!! There’s food mixed in too… Tommy’s, dim sum in Chinatown, pizza in North Beach. & the whole thing takes us through a little SF history along the way.
Besides getting to & from Tommy’s in The Richmond, everything else is walkable. ~2.6 miles total, with most of the walking upfront.”
Disclaimer: this crawl also included people who didn’t drink. Bar crawls can have a reputation of landing you on your ass by the end of it but there were NA options & we had food mixed in. Did those of us who did participate in the drinking still end up mixing a ridiculous amount of liquors? Sure did… but it was worth the headache that next day.
Tommy’s Margarita
Tommy’s Mexican Restaurant is a deceiving place. The first night I moved to SF in 2019, my dad & I were trying to find a place that was open to grab some food & stumbled upon Tommy’s. We had eaten there that night & I had never gone again. It wasn’t bad, but it is in a location that you have to seek it out if you’re in any other part of the city.
I didn’t realize the infamy of this place until 2023. I was in NYC for the fall & I had taken a trip to London. While I was there, I was at a speakeasy called The Blind Pig. I had told the bartender that I was in NYC for the fall from SF. He then went “San Francisco?? Have you been to Tommy’s??” I didn’t even know what Tommy’s was off the top of my head. I had to Google it & I was like “wait I have been to Tommy’s.” He then proceeded to tell me the lore of Tommy’s. Tommy’s Margarita is only 3 ingredients: tequila blanco, fresh lime juice, agave. They call it the original ‘Skinny Margarita’. Tommy’s son, Julio, is the ambassador for all tequila for North America so he trains & teaches top bartenders from all over the world. Some get selected to do an immersive training program at Tommy’s in SF & this is why you will see Tommy’s Margarita on a lot of top cocktail menus internationally. In 2025, I had been at the Chelsea Hotel in NYC grabbing a drink with a friend & we saw this on the menu.
Buena Vista Irish Coffee
This has to be the most recommended drink of SF. To watch one of the bartenders make 10 of these at a time is truly a treat. The sugar cubes go in, then the coffee & they stir them while splashing coffee all over the place.
The first time I ever visited SF was in 2015 on a family vacation. I was 17 & had just graduated from high school a week prior. We stayed in the Fisherman’s Wharf area. I really loved coffee in high school. I still do... but I especially loved it then. My family had kept talking about the fact that we had to go to Buena Vista to get an Irish Coffee. I had no fucking clue what an Irish Coffee was… I just kept hearing that it was a delicious coffee drink.
We sat at one of the round tables in Buena Vista. I remember we had a Stanford engineering professor & his daughter sitting with us at the table. The server came up to take our orders & around the table everyone started ordering Irish Coffees… it got to me & I confidently ordered an Irish Coffee as well. Nobody said a fucking thing. Now, I did just graduate high school & I was about to go to college so it wasn’t like a big taboo thing that I drank at the time, but it was at high school parties or in a friend’s basement, not ordering drinks at a bar or restaurant. My Irish Coffee came & I was like “What the fuck? Is there alcohol in here?” & my mom goes “Yeah… I thought you knew. You just ordered it so confidently that I didn’t say anything.” My palate wasn’t very mature at the time so I was not a fan.
Now, the reason that the Irish Coffee became so infamous at The Buena Vista was that in 1952, the owner had challenged a travel writer, who had just had an Irish Coffee at the Shannon Airport in Ireland, to help recreate the drink. They failed & eventually the owner even went to Ireland to learn how to make it. Apparently the trick was that the cream had to be aged for 48 hours in order for it to be able to float on top, rather than sinking to the bottom.
On the crawl, we got these to-go & went & drank them near Aquatic Park (it can be hard to snag a spot in Buena Vista on a Saturday). Getting them to go & sitting by the water is just as lovely.
Now, to get from Tommy’s to Buena Vista…
We had taken two separate Ubers. The traffic was brutal near Buena Vista (tourism was up that weekend because the SF marathon was the next day).
In one car, it was me & my two friends who were in “I ♥…” shirts. Mine was an I ♥ SF shirt & theirs were I ♥ NY shirts. This has been a running bit within our friend group because exactly two years prior, we went to cheer on one of my friends who was running the SF half marathon & it was a chilly morning so I had a sweatshirt on. I like to wear white tees under sweatshirts or long sleeves… for the vibe. Sometimes I will grab whatever white tee is accessible because in San Francisco, you usually don’t take that layer off. This day it ended up being hot as fuck as the day went on & here I am in this cropped white I ♥ NY shirt. I could not have gotten more shit when I took my sweatshirt off. The reason I had this tee was that I was in NYC the fall prior & was going out with friends for Halloween. I had to come up with a last minute costume so I went as a NYC tourist. I even went to fucking Times Square just to get this shirt that day. Turns out her other friend, without us talking, decided the same exact thing… so it worked out perfectly.
Then the next year for Halloween, after this happened, my dad was in town for the weekend & my friends were throwing a Halloween party. We needed another last minute costume & I was like perfect this time we can be SF tourists. So my dad & I showed up in matching I ♥ SF shirts as a bit.
It doesn’t stop there… In 2025, our friend group went to NYC because we had our friend’s engagement party in Greenwich, CT. We were all staying at separate hotels & I was on a mission to go to a restaurant I loved in NYC, but it was hard to go with a group so I went to dinner separate from everyone & met up with them for drinks at Cubbyhole that night. I got there first since they were all still wrapping up dinner & they showed up bundled up. Meanwhile it is the end of July in NYC, so it was hotter than balls. They then get all dramatic like “god isn’t it warm in here?” Like no shit, you guys have jackets on in the middle of the summer. Then they all collectively take them off to show off their I ♥ NY shirts that they bought in Chinatown that day. It was so fucking funny.
I knew I had to wear my I ♥ SF shirt for this crawl. One last usage of it. Then my two friends who were in NYC that night, wore their I ♥ NY shirts. That left the rest of the group with normal clothing. Like I said, all 3 of us were in one Uber with everyone else in the rest. We got to Buena Vista first & we started ordering all of the Irish Coffees for the group. We were like damn they must’ve really gotten stuck in that traffic. Then they finally stroll up all in different I ♥ SF shirts. They saw a shop when they got out of their Uber to walk the rest of the way. It was perfect.
Russian River’s Pliny the Elder
The location for this felt fitting to match our outdoor part of crawl. From Aquatic Park, there was a walking path that I wanted to take people on. It traced a common route that I would walk throughout my time living in North Beach. By the end, I found it hard to fully appreciate the walk because I had walked it hundreds of times, but objectively, this has to be some of the best views of the San Francisco Bay from this route. I found it fun because everyone in the group had lived in SF for 2+ years & not a single person had walked this route before the day of the crawl.
We passed through Francisco Park. We passed my first apartment in North Beach. We passed by Coit Tower. Then we landed at Washington Square Park (coming at it from walking south on Stockton St).
This is where we picked up some Pliny’s from Luke’s Local around the corner & had them in the park. Gotta be careful with a Pliny… it can get ya with it being 8%. For the sake of our livers & the marathon we were on, we just split a couple among the group.
I grew up around the beer industry & it wasn’t until trying Pliny for the first time… that I started to like beer. It was the first beer I was ever excited about at 25 years old. I associated a lot of beer with light beers & I never wanted to drink beer in college or after. I opted for liquor, seltzers or wine. NEVER a beer.
Pliny awakened my taste profile for beer. There is something about the Pliny lore that I appreciate too. This past year, I finally got to try Pliny the Younger for the first time. This is their seasonal triple IPA that they produce in limited batches. People travel from all over to their Russian River tap rooms to get it during the couple of weeks it is available at their tap room. They also have limited kegs that go out to bars in SF & they will announce if they are tapping them. I had been attempting to try Pliny the Younger for a few years now & the stars finally aligned. I had seen that Casements in the Mission was tapping their keg on a Monday or Tuesday afternoon so I went over to have a pint of it.
The story with the beer being named after Pliny was that Pliny the Elder was famous for dying while trying to save people after the eruption of Mount Vesuvius. But why name a beer after him? He was also an author… & in his writings, he had one of the first recorded references to hop vines (which we obviously know is very important to a Double IPA). There wasn’t just “the Elder” though. You had his nephew & adopted son, Pliny the Younger. Pliny the Younger was a witness to his uncle’s heroic move to go try to save people, but he stayed back & survived.
Chinese Mai Tai
Next up was the Chinese Mai Tai from Li Po Lounge. Technically you can get it at other bars in Chinatown. I had Buddha Lounge on the list as a backup in case Li Po is too busy, but Li Po has the trademark for the original recipe of the Chinese Mai Tai. I couldn’t find an actual answer on what exactly is in it, but you must know… there is an unspoken rule at Li Po Lounge that people should only get two of these max.
We ended up in the basement of Li Po lounge with our Chinese Mai Tai’s & this is where the crawl started to get sillier. They were playing 2000s hip hop & rap in the basement. It was so thick & humid down there with random couches everywhere. It truly felt like we were in a frat basement.
& I can’t forget to mention that this is a spot that Anthony Bourdain has hit on a trip to SF.
This stop also included a pit stop for dim sum in Chinatown.
Martini
There is a loose claim that the martini was invented in SF at the Occidental Hotel. I say “loose” because this is very much so a reported story of it but there are claims it actually should be credited to Martinez, CA. Whether it was or was NOT invented in SF officially, this story still ties it back to San Francisco. Plus, I will never say no to a dirty vodka martini so I was happy to add this to the list.
We needed to go somewhere that would represent this era of time when the martini was tied to the city. The original Occidental Hotel was destroyed in the 1906 earthquake (along with most of this area of SF), so we couldn’t go there. BUT there is still one place that is leftover from the Barbary Coast era & that is the Comstock Saloon. It was originally the Andromeda Saloon that opened in 1907, during the rebuild period after the Earthquake. It is right around the corner from The Montgomery Block (aka the Monkey Block). Now the Transamerica Pyramid is built where this was. Bohemian culture set the stage for this part of San Francisco. I think the origins of a place can define its foundation & DNA. It then drew the Beat Generation afterwards. Why has this part of San Francisco been such a literary haven for people? This question has haunted me on walks through North Beach & Jackson Square. One thing about The Bohemians & The Beats… they didn’t shy away from having a drink.
During the Super Bowl earlier this year, I was walking through North Beach & actually saw Jason Kelce outside of Comstock Saloon. He had been doing a video series where he was shotgunning beers all around SF. There was someone dressed up as Emperor Norton outside that Kelce was interviewing. It made me laugh getting to witness this on my walk. I’ll let you do your own research on Emperor Norton. It’s quite amusing & paints the picture of another character of the past of this part of San Francisco.
Fernet-Branca
What city is the top consumer of Fernet-Branca in North America? (A trivia question that loves to be asked at bar trivia in SF). ding, ding, ding It is San Francisco. SF is not the top consumer in the world though, Argentina beats them in that. (I actually got that question wrong at bar trivia once after being quite overconfident). Being from the Chicago area, I like to say Fernet is to San Francisco what Malort is to Chicago (except Fernet is obviously not made in SF). It became a cult classic among bartenders & others in the industry in the 90s. Then it just kind of took on a life of its own.
You can get a Fernet shot at most places in SF, but obviously the best place to go is a classic North Beach bar. There are so many historic bars in North Beach & any within the cluster is worth going to. Vesuvio is my favorite, but I knew on a Saturday night that there was no way we were getting in there. I only enjoyed Vesuvio in the afternoon or on a week night… it actually looks like my worst nightmare to walk into on a weekend night.
We chose to go to Specs’ for our shot of Fernet. The consensus among the group was one of pure disgust. We got a couple of shots for people to share & split, but it was more like a rocks glass filled way higher than it should’ve been with Fernet.
Specs’ is actually a really interesting spot though. A lot of history is baked into Specs’. So the building actually has the alleyway where Specs’ is & the front of the building is out on Broadway St. It is the Garden of Eden (I think you can guess what this is). For those who haven’t been to North Beach, there are strip clubs baked right into the main strip of the neighborhood, off Broadway. Now this really ties back to The Barbary Coast era… where this was the red light district of SF. It was lawless. Like I said earlier, I think that the origins of a neighborhood can live within it over the years. As much as things evolve over time, roots are roots.
Where Garden of Eden is now used to be Tommy’s Place & Specs’ (full name is Specs’ Twelve Adler Museum Cafe) was 12 Adler Place, the alleyway bar. These were interconnected lesbian bars. Tommy Vasu was the first lesbian to own & operate a bar in San Francisco. Richard “Specs” Simmons who opened Specs’ in 1968, had followed a girl to North Beach, where he eventually stayed. This girl apparently used to hang out at Tommy’s Place & 12 Adler Place. I like that he kept the nod to 12 Adler Place in the name.
Wine from Napa (Clos du Val)
We know that when people think of SF, they think of Napa. It is a 1-1.5 hour drive from the city. When I was 22 & had just moved out to SF, my family was visiting & we had a group of us that went up to Napa (family friends & a couple of my friends). Our second tasting of the day was at a winery called Clos du Val. It was in Stag’s Leap.
Walking in… it feels like exactly what you would expect from a winery in Napa. The entire vibe was immaculate. One of my family friends was older than me & had been living in SF for a few years at that point & she was like “you gotta get a wine membership.” I could tell that Clos du Val was where I would want it at. My decision making was also a little hasty after our tasting there so I signed up. I have a very clear memory of the fact that our server for the day was also a singer & as I was signing up, he was singing in the background to our group.
I had different people who would visit from out of state & we could go up wine tasting for free. I actually started a really solid collection of wines from Napa from that period, that I have kept & have been aging. I am not sure who I thought I was at 22 years old. I acted like I had a fucking wine cellar. Eventually I wasn’t going up to Napa as much & the wines really started to pile up so it was time to cancel the membership BUT it definitely got its usage for the 4 years I had it. This was actually a mess I had to clean up during my move out of SF… What do I do with these wines? They are now in wine storage in SF. Who knew that was a thing? A whole part of a storage facility just dedicated to lockers for wine only.
One thing about me is that I love a good story too. & Clos du Val had a great one. The owners hired a French winemaker to go to CA & find the best land to grow Bordeaux style Cabernets & they landed in the Stag’s Leap region. This was back when you could buy the land for a much cheaper price. Clos du Val had been in The Judgment of Paris in 1976 with their 1972 Cabernet. This is where Napa Valley was really put on the map as a respected wine region in the world. It was the first time a CA wine beat a wine from France. Stag’s Leap Winery took the top spot for reds that year. They argued that it was unfair because of how young the Napa wines were. They wanted to test them against the Bordeaux wines after they had aged. So they did a 10-year anniversary rematch of all of the same wines in 1986. In this rematch, Clos du Val scored as the top red wine, proving how well it aged.
This is the winery I will always recommend in Napa. I have gone to others & nothing fully matches Clos du Val in my eyes.
Coming up with this crawl was a fun creative process. I walked the route beforehand to map it out & know the exact mileage to ensure the logistics would work. I went to the SF Public Library to print out each little photo to cut out… & I even bought a glue stick just for this. I found this was a really fun thing to plan in the middle of the chaos of moving. It felt like it was something that could properly honor my time in SF & it was a way to productively put that grief into creation. It was one of those adventures that I will remember for the rest of my life. SF is very special to me & it always will be… even if it wasn’t the best place for me to live anymore.
