San Francisco is a good town for bookshops. This is a route I’ve done a few times. It’s like a bar crawl, but with fewer alcoholics.
Start at Stout Architectural Books. This is a great shop for flipping through pretty picture books – think Phaidon, Taschen, etc. Most of what they carry is foreign to me, and not the type of book I am likely to come across elsewhere. I can spend a long time here.
From Stout, it is only a few blocks to City Lights. This is the most famous bookshop in the city. It is always be packed with tourists, which makes it less pleasant for browsing. It isn’t a large place, considering the size of their collection, so you’re constantly squeezing around people in narrow aisles. But I seem to only end up here on weekends – weekdays may be better. If you are here on the weekend, you should see the legendary V. Vale and his RE/SEARCH Publications table just outside, in the alley between City Lights and Vesuvio. Make sure to browse his wares.
If you need a potty break at this point, you’re in luck. San Francisco is notorious for how few publicly accessible bathrooms it has, but one of the nicest is just a few blocks away at The Ritz-Carlton on Stockton & California. Walk in the main entrance like you belong. Try to project an aura of being parvenue and you’ll fit right in. Take an immediate left, and in maybe 10 or 15 feet there will be a short hallway to your left. The bathrooms are at the end of that hallway. No keys or code required. I don’t always defecate in this part of town, but when I do, I poo at The Ritz.
The next bookshop, Green Apple Books, is across town in the Richmond. This is the best general-interest bookshop in the city. It doesn’t look like much from the street, but is deceptively large inside. Of all the shops, this one takes the longest to browse. It is about 4 miles from City Lights and The Ritz, so if you’re on foot you might want to jump on the 1 California.
From Green Apple, head two blocks west to Pho Huynh Sang. This is, in fact, not a bookshop. But they have good phở and bún, so I pretty much always eat here when I’m in this part of town and can justify a meal. The staff is friendly and the place is big enough that there’s always a place to sit without having to wait in a line.
After you’ve had a meal, you are allowed desert, so you might as well walk one block east back to Toy Boat. I usually buy a loaf of the banana bread.
The final stop is Borderlands, recently relocated to the Haight. This is our genre bookshop – scifi, horror, fantasy. I’m only interested in the first of those genres, so I don’t usually spend too long here. But I do like to at least peruse the new arrivals table in the front, and the used book shelf in the back room under the office window. The staff here are exceptionally good at recommendations. Give them the name of some obscure SF book you liked, and they’ll be able to recommend something else similar. You don’t even need to remember the title – just give them a vague description of the plot and what the primary color on the cover was and they’ll probably know what you’re talking about.