There is a definite difference of character in Market street, once you head south-west (and a little uphill) away from the phenomenally sleazy downtown/civic center region. Things are pretty slick, but without that dull yuppie sameness that often infects upscale neighborhoods. This is usually called "The Upper Market", and it's essentially on the border of "The Castro".
You might want to save the Upper Market (and the Castro itself) for a late-night expedition, since it tends to run later than most places in the city, but it's a fun afternoon/evening place as well.
The L runs up and down Market 24 hours, so that might be the way to get there. If you're coming from somewhere else, the 24 line might be convenient, it runs down Castro, and you can pick it up in places like the Lower Haight (going south on Divisidero). From the Mission, I might just walk on over... they aren't that far apart (if you follow 16th Street West from the hipster strip by Valencia you'll hit Market Street where the Bagdad Cafe is... and if you follow 18th Street West, that'll take you to the center of the Castro.
Anyway, starting with Church Street a block south of Market St:
- On Church, at the corner of 15th Street, there's a very detailed mural by Mona Caron that covers a history of San Francisco in timeslices superimposed over Market Street. I like the view of The Future in the final frame... Reference
- At 262 Church Street, (between 15th St & Market St), there was one of the legendary, funky coffee houses run by the same Arabic family that were key to the SF hipster scene. Now it's under new management, it's called "Church Street Cafe" rather than "Muddy Waters", and it remains to be seen if it's worth much of a mention at all.
- Sparky's, Church St, also just south of Market street, on the other side of Church. A 24 hour place. Basic diner stuff.
- Azteca, Church Street, on the block south of Market. My current pick for Best Burrito in SF. Chile Reno Burritos are pretty cool.
- Aardvark Books, right next door to Azteca, excellent little used book store.
- I'm not sure what's up with the bar The Transfer on Church (very close to Market, right at the south-bound stop for the J line). They were doing some popular dance music events, but the word is they've been messed over by ownership changes recently... (Reference). Try "the Knockout" (way South on Mission St) instead? Reference
- Tucked away behind the Supermarket complex there is the "Duboce Bikeway" with another, totally brilliant, Mona Caron mural stretching along the whole length. This is a must see, a tribute to San Francisco cycling, from Ocean Beach to Critical Mass. Reference
Now moving up-hill on Market Street (toward Castro):
- Open Minds Music, recently moved to this new location on Market Street, between Church St and 15th Street. Nice, medium sized place, heavy on the vinyl, as I remember it. Reference
- Cafe du Nord is at 2170 Market, a little north of the Market/15th/Sanchez intersection, on the north side of Market. Downstairs, there's a classic darkwood bar with an attached performance/dance space. Reference.
- Orbit Room, 1900 Market at the corner of Hermann. The place where coffee and alcohol people go to meet, because it's one of the few cafes that try to do both well. The atmosphere has been called "deco-industrial" (by the now defunct "Digital Lantern" website), and I can't do any better than that. Open to midnight, 2am on Friday on Saturday.
- Bagdad Cafe, Market and 16th. Decent diner food. 24 hour place. A slightly different kind of hipster crowd than Sparky's.
- Sweet Inspirations - between Sanchez and Noe. One of the best places in San Francisco for serious desserts. Super-rich, huge portions (consider splitting a piece with someone). Open fairly late, like around midnight.
- IXIA - The window of IXIA is often worth a look: this is a florist with a creative style on Market between Noe and Castro.
- And as you get near Castro, right before 17th Street, you'll be going by a legendary piercing/tattoo emporium, formerly the Gauntlet, but now Cold Steel. Step right up.