It would have been difficult to have had a less favorable impression of the city of San Francisco than my girlfriend and I did on our first excursion into town. We headed in looking for lunch and decided to stop off in the Mission, the first point of interest on our list of things to see. We started somewhere near 21st and Van Ness and walked up Mission Street looking for a nice cafe to sit down and grab some food but it became quickly apparent that we weren’t in the right location for that. We wandered through several sketchy blocks and grabbed a hasty meal at an overpriced and underwhelming Mexican restaurant before jumping back into the car to see if we could find the awesome San Francisco that we’d heard about.

We drove for three hours, covering neighborhoods from the Marina to Sunset to Height. Every time, we managed to miss all the interesting stuff and only drive by the low rent or completely residential areas. I realized after a while that all I wanted to see were some bars to give some indication of life in a city that otherwise appeared to consist of nothing but homeless people or sterile rows of townhouses. I counted four bars in three hours. Needless to say, we were pretty discouraged by the end of it.

We met a friend for dinner and she managed to talk us off the ledge. She gave us some more perspective on where we should have gone and we devised a plan to see the “real” San Francisco. That core of that plan was actually to Google “bar” and see which areas of the city had some sort of concentration of a social life. It proved surprisingly effective.

Two days later, I dropped my bike off for service and set out with a mission to walk through every neighborhood in the city that I could. Using the route derived from the “bar” search, I wandered through 12 miles of hills and, this time, the journey was far more positive. I managed to cover the brief but classy Hayes Valley, the hippy feel (and smell) of Lower and Upper Height, the sketchy streets of Tenderloin, residential Sunset Heights, the preppy retail empire and nice restaurants of the Marina, the quiet dignity of Nob Hill, and (briefly) the breadth of the Mission. Neighborhoods in San Francisco seem to extend East-West for a ways but are extremely short when you walk North-South. I was constantly surprised how much of a different two blocks could make.

The housing situation is a total madhouse. I went to a couple of open houses that I found on Craigslist and they are packed from the moment the doors open. People show up with custom-made “renter’s resume” packets and gladly compete to pay 40% more than the previous tenant of that particular dump. I rented in New York and, while prices haven’t quite yet hit those levels in San Francisco, they are alarmingly close and the whole process seems even more grueling. Since apartments typically fill immediately, landlords aren’t in the habit of posting anything more than a day in advance. I guess I’ll be showing up in October with a moving truck and nowhere to live.

The two standout neighborhoods were the Marina and the Mission. The Marina really felt familiar with its nice stores, nice restaurants, and nice cafes throughout. There were people all around and everything about it was lively and, well, nice. The Mission was a bit of an ugly duckling neighborhood to me. Luckily I got advice to stay west of Valencia and that helped introduce me to the friendlier parts but it’s still definitely a place with more character than class (and a whole lot of hipster).

I met up with several friends in SF and they all pointed me towards the Mission as a place that fostered interesting vibes, creative people, and a certain gritty persistence that seemed custom tailored to the startup community. I’m still not completely sold on the area, but I’m certainly open-minded about it and more than a little curious to see what it has to offer.

As far as the startup scene goes, my brief time in the Bay Area certainly wasn’t a waste. I met up with some local tech bloggers, attended a few meetups, and generally got the impression that no one is more than a degree removed from someone in the business. Every night of the week, at least a half dozen different events demand your attention and there is an underlying buzz of energy that I haven’t found anywhere else. I’m glad that my hopes for finding a dedicated and dynamic community weren’t misplaced.

The most surprising part of my west coast visit was how positive my experience was in Oakland. My step brother lives out there with his wife and they have a wonderful apartment in an area (near Lakeshore Ave) connected to all kinds of nice shops, restaurants and bars. We spent a few nights going out locally there and it definitely grew on me. Were I not so adamant about living in the city itself to stay as plugged in as possible, I’d definitely put living in Oakland high on the list of possible alternatives. The only downside is that once you leave the city, it seems to take an incredible amount of energy to overcome the inertia preventing you from crossing the Bay Bridge back to San Francisco. I’d liken it to living in Queens in New York but without the same quality of public transportation back into the city.

Overall, I’m very happy that we got a chance to scout out San Francisco, whether that is from the perspective of understanding the housing situation, getting a feel for the neighborhoods, or dipping into the startup scene. After having sampled my future life in the city, it will be difficult to rejoin my quest to see the country without having that other part of my mind just wanting to dive in and get started. Difficult, but not impossible. There are still a whole lot of miles of USA yet undiscovered and I’m supremely excited make my way back to New England for the next leg of my journey. Some of the best parts are yet to come.