A Series Of Stupid Events OR How I Ended Up In San Francisco

I don’t really know how this came about. Back in July I randomly got the urge to go to Seattle as I’ve never been there before. I knew my friend (I use this term loosely as we’re not super tight) had just moved out there with his girlfriend who is originally from there. In any case, I hit him up out of the blue and asked if it would be possible for me to crash on his couch sometime in September. He said it would be no problem and to just keep him posted.

Cut to the end of August and I’m at Andrew and Angelina’s wedding. I met up with Marcell and she tells me that she goes to school at Berkley in San Francisco. I offhandedly mention that my cousin Josh lives north of San Francisco and that if I ever go out there to visit him that I could visit her too. She seems receptive to this idea (probably because she thinks I won’t follow through).

Cut to a couple days later, September 2nd, and I hit up Ryan (my friend in Seattle) via email to see if he’s still down to let me crash with him. A few days go by and I don’t hear back from him. A few days later I come to the realization that Seattle is not only a short flight from San Francisco, but I remember that my friend (I use this term loosely as we’re not super tight) Shawn lives in San Francisco with his girlfriend. I send him an email saying basically the same thing I wrote to his brother and explaining that I was gonna try and kill two birds with one stone. Fly out to Seattle, spend a few days there, fly down to San Francisco spend a few days there (see my cousin Josh, crash at Shawn’s place (and go to bars with him at night) and see Marcell), and then fly home.*

I then waited a few days but heard no response from Shawn or Ryan. I then decided to call Josh. Not to try and crash with him, but to see if he’d still at least be available to meet me while I was there, if I was gonna be able to a) get Shawn’s attention and b) if he gave me the green light. After a few days of no response and a bit of telephone tag, I finally got a hold of Josh. At this point I had decided “fuck it,” neither one is getting back to me but I’ve had it in my head that I want to go on trip so I will at least go on one. Since there were/are more potential people to meet up with in SF (Josh, Shawn, and Marcell) than there are in Seattle ( just Ryan) -in spite of the fact that I’ve never been to Seattle and I really want to check it out- there were too many signs (things on TV and Instagram) pointing me to San Francisco.

When I finally got a hold of Josh, he told me that my timing was perfect. He was planning on driving from SF to Boston to drop off a friend and chill on the East coast for a few days before grabbing a girl friend of his and driving back to SF. He said that I should not spend my money on a plane ticket out there and instead just drive with him. Initially my reaction was positive but the second we hung up my heart sunk and rational Kyle kicked in. I didn’t really want to do this but I needed a reason not to, so I made a Pros and Cons list.

Pros: 1) I have to time to do this (since I quit City Express) 2) it’s a road trip, those are always fun 3) the spirit of adventure 4) I get to, at the very least, definitely see Josh. Cons: 1) having to pay for gas 2) it would take longer to get there 3) I have to deal with his schedule, wait for him to drive out here, spend a few days in Mass, then drive to SF 4) I have to bend to his plans; sort of already said but whenever I want to do something and Josh gets involved, it turns into us doing whatever he wants to do 5) I didn’t want to have to pay for motels or worse, have to sleep in his car 6) I don’t want to drive; I really don’t like it 7) I don’t want to have to deal with this girl I don’t know and feel like the third wheel the whole time.

A couple days later I booked a flight and a CHEAP hotel. I then emailed Josh my Pros and Cons list and apologized for getting his hopes up. …and so that is what led me to go in this semi-sporradic, Frances Ha-esque vacation.

*Actually the initial plan included a trip to New York to chill with Steve and Tom again and that I’d fly out from JFK; so the trip would have been as follows: Boston to New York (via bus), New York to Seattle, Seattle to San Francisco, and San Francisco back to Boston. But I didn’t want to throw this in the mix to make this already confusing and unnecessary backstory even more confusing.

San Francisco – Day 1

Friday 9/26 – I arrived at SFO at 12:56 (Pacific time), 36 minutes earlier than our scheduled arrival. This was good because it meant a slightly shorter flight, but bad because my check in time was not until 3pm. Oh well. I made my way from the terminal to the BART and began the ~30 minute ride from the airport to the Powell Street station in downtown San Francisco. From there it was a relatively short walk to hostel. I explained the situation to the woman at the front desk and she said I could leave my bags there and get them later (when I checked in). I then walked aimlessly up Mason street to Huntington Park at the top of the hill. There I got situated, figuring out where I was and putting on suntan lotion before walking back down to get food.

The place I ate at was across the street from my hostel. While eating, I texted my friend Shaun (who moved to SF for work upon graduating) to let him know I was in town and that we should chill if he wanted to. After eating I  checked in and brought my bags to my room. My first mission was to locate the hotel I had stayed at the last time I was in SF in 2006. The hotel was only a few blocks away near Union Square.

UnionSquareUnion Square

The moment I got there I remembered everything and knew exactly where I was. After admiring Union Square for a bit I took a cable car to Fisherman’s Wharf. After exploring for a bit I walked to Pier 33 to book my Alcatraz tour. The sign said that the next available tour for purchase was September 30th. However, when I asked if there were any tours sooner, the woman said that if it was just for one that there was a cancellation for the tour on Sunday at 11am. Sold.

I then continued to make my way down the Embarcadero. As I was walking, I noticed that this all looked familiar. I knew where I knew it from but I wasn’t getting to the main part of the attraction, the part that was so iconic to me. Suddenly, I saw it…

THPS_SculptureThe sculpture you use to get to the hidden tape in Tony Hawk Pro Skater.

The sculpture from Tony Hawk Pro Skater! Also, featured in THPS4, this sculpture is used to get to the hidden tape in the level. This area is not very accurately portrayed in THPS 1, but it is super accurate in 4. I saw…

EmbarcaderoStairsStairs featured in Tony Hawk Pro Skater 4.

the stairs you grind on in one of the challenges,

BigStairsMore stairs featured in THPS 4.

the big set of stairs you have to jump in another challenge,

StreetCarStreet cars and the Embarcadero are also featured in THPS 4. The building in the background is the Exploratorium.

and the awnings and street car wires you have to grind on in the C-O-M-B-O challenge! I felt like I was living the video game. After nerding out for a bit and seeing a bit more of the Piers and the Embarcadero, I noticed a tower at the top of a hill in the distance. Since this first day was purposely unstructured in order to allow for free roaming, I made my way towards it. However, before doing that, I felt I needed to make an important stop first. Along the way I went by the Transamerica building.

TransamericaBuildingThe Transamercia building has a small forrest of redwoods in which their employees can eat lunch and relax.

This building is so iconic to San Francisco and I hadn’t gotten a chance to see it the last time, so I was glad to pay my respects. Next, using mostly my eyes (in other words, not relying on the Maps app on my phone) I walked to Telegraph Hill. Along the way -as I climbed the various hills- I got stunning views of the city and of the Transamerica Building. Eventually, I climbed a series of stairs and got to the top of Telegraph Hill.

SF_SkylineSan Francisco skyline from atop Telegraph Hill; the Bay Bridge on the left, the financial district in the middle and the Transamerica building on the right.

At the top I got a great view of the financial district and the Bay Bridge. Behind me was Coit Tower. Unfortunately by the time I got there (I think around 6pm) it was closed. I don’t really know if you’re typically allowed inside or to the top, but I didn’t really care, there were still great views of the city from the bottom to of the tower.

CoitTowerCoit Tower

Once at the front side of the tower there were great views of the Golden Gate Bridge (see my Instagram). I took a few pics before using the public restroom* and making my way back down the hill.

SF_SunsetThe sunset on the way down the hill.

I ended up going down a different side than I walked up. I then made my way through the outskirts of Chinatown to start heading back downtown.

HippieVanSaw this Hippie van with the church and the clouds behind it on the way back downtown and couldn’t not take a picture of it.

As I did, I walked past Tonga Room/Hurricane Bar at the Fairmont Hotel. I knew about this bar because my friends had gone to SF about a year ago and had posted it on Instagram. I started to go in but immediately felt out of place based on how I was dressed. After going back to my hostel to change, I walked back to The Tonga Room.

TheTongaRoomThe Tonga Room/Hurricane Bar at the Fairmont Hotel.

Because I was by myself and didn’t need a table, I was able to go right in and grab a seat at the bar. I told the bartender that I was/am not a fan of mixed drinks, that I’m more of a beer drinker, but that I felt I should have a mixed drink since I was at a tiki bar. He recommended the Chi Chi and it was the perfect choice. I don’t know if the bartender made the drink weak or just blended it really well, but either way, it was delicious and I could not taste the booze.

ChiChiMy drink, the Ch Chi, a twist on a typical Pinã Colada.

The Tonga Room reminded me of a Boston area staple, Kowloon on Route 1. The difference being that Tonga is much nicer and brings it to the next level. In the middle of the restaurant/bar there is an actual lagoon. On the lagoon there is a small boat, and on the boat there is a house band that plays short sets every 15 or 20 minutes. While I was there, I even experienced a “rain storm.” The lights flickered, there were thunder sound effects, and there was even “rain” that fell from the ceiling into the lagoon. It was a great way to end my first day.


After my second drink, an Anchor Steam beer, I made my way back to the hostel and straight to bed.

*SF is great with public restrooms. This is a concept I wish more major cities would adopt. It is super convenient to get the urge to go to the bathroom and have a free one available nearby without having to go into a restaurant that probably wouldn’t let you use their’s anyway.


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