San Francisco: Day 1 of 5

As you can imagine, I was up at the crack of dawn on Wednesday. After having a quick shower, I called a cab and was out the door around 4:30 a.m. I got to YVR just before 5 a.m. and sailed through Customs (always a blessing, when that happens). My 7:00 a.m. flight to PDX left on time, however, my 9:30 a.m. connecting flight to SFO did not. When I finally landed in SFO at 1:00 p.m., I was so incredibly happy to walk outside and see this.

Palm Tree

Pure sunshine.

I hopped into a cab to drop my stuff off at Vince’s. The day before, Vince had given me some pretty hysterical instructions on how to find the spare key and get into his place. When I got inside, I met one of his roommates who then offered to drive me down to his office so I could say hi. (Talk about a warm welcome!) After popping in and saying hello to the Planwise team, I ventured out and did what any West Coast girl would do: walked along the water.

San Francisco Fire Department

San Francisco-Oakland Bay Bridge

One of my girlfriends and I have a running joke (ok, it’s probably not a joke) about how much she loves firemen and I love sailors. Knowing that, I had to capture the fact that the first guys I met in the city were sailors in the San Francisco Fire Department (SFFD). This boat was actually built in British Columbia in 1951 and served in Vancouver until 1987 (cool, eh?). Then it was retired under the name Fireboat #2, which it is still known as today in the SFFD.


There are so many piers in San Francisco that run perpendicular to the shore; I walked up and down almost all of them.


“Blue sky, you are my only witness.”


The view of Alcatraz from Pier 39. Unfortunately, I wasn’t able to go on a tour (day or night). Everything was sold out weeks before I left and the earliest tours available right now are in mid-August. (Seriously. If you’re going to San Francisco sometime after mid-August, purchase your tickets online now!) While I’m sad to have missed out on this, I can say that it’s probably the only thing on my wish list that I didn’t get to do… so that’s pretty good.

Fisherman's Wharf

Without planning to, I ended up walking from AT&T Park all the way to Fisherman’s Wharf. It becomes pretty apparent, even before you get to it, that everything between Pier 39 and Fisherman’s Wharf is meant strictly for tourists. The area is just full of small shops selling the same t-shirts, keychains and hats. I walked in and out of it all pretty quickly, stopping for nothing other than to see if any sea lions were out (none were).

Food at Fisherman's Wharf

I also couldn’t help but notice that every food shop at Fisherman’s Wharf sold the same stuff and it all looked like what you see here. (This all looks disgusting to me, but I thought it might interest some of you.)

Lombard Street

I then realized that it was already after 5:00 p.m. and I had to be back in the Financial District for a Meetup at 6:00 p.m. As if the 5K walk I had just finished wasn’t long enough, I decided to walk back. Crazy, right? And where did I start? By taking a detour and hiking up Lombard to see this famous windy street, of course. It was actually pretty cool… but I’m pretty sure this hill is the reason I’ve had a blister on my heel ever since.

Cable Car

I could seriously feel the blister forming, as I walked back down Lombard. Serendipitously, I stumbled upon a cable car, which carried me most of the way back to the Financial District. There, I attended my first Bay Area FinTech Startup Meetup – an event Vince hosted and where more than 100 startup founders and employees listened to 4 startups present their product and ideas. StockStats, Jemstep, Planwise and Puddle all presented this month. Based on the presentations, Planwise is still the only one I’d use, but it was cool to see what other people were working on.

After the Meetup, a few of us popped into a pub for an hour, before Vince and I headed back to his place and crashed. Honestly, after waking up at 4:00 a.m. and travelling all day, I’m amazed I stayed awake until 11:00 p.m. It was a great first day in the city and I can’t wait to share pictures and stories from the other days…

  • Great pics of San Fran, Cait. You sure covered a lot of activity on your first day there. Thanks for sharing with us.

  • Day 1 of your trip sounds amazing! Sounds like you took in a lot of San Francisco on your first day. I’m pretty sure I would have been snoring after getting off the plane. Can’t wait to hear the rest – your pictures are awesome!

  • Cait, I was so excited to see this post of your first day in San Fran. My husband and I, along with 2 other couples are going there in September. I have never been and I can’t wait. We were lucky enough to already book Alcatraz, as we had heard how quickly it fills up. Can’t wait to see your other posts! Have fun!

    • So happy to hear you got tickets to Alcatraz already! You guys are smart ;) I have a couple more posts to write but I will say that my one other piece of advice would be to bring a jacket and layer up! It gets so freaking cold at night. (I was not at all prepared.)

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