I like to ride up the waterfront, from Pioneer Square or the ID, to Golden Gardens. Heading back into civilization usually means climbing Ass Kick Hill until you're at the top of Phinney Ridge. Then the reward for all of that is to head down Fremont Ave. I always want to scream "No brakes no brakes no brakes" but luckily I can usually recognize when something has "bad idea" written all over it...

I've never tried 4th Ave on the north side of the hill, but will have to give that a try. Third is just barely doable, but what an awful climb! I've found that it can be easier from the south if you start at 5th Ave, near the Mercer intersection, and then climb whatever that turns into. It goes by Trolley Park ( or something like that ) and lets off at the top of Nob Hill, slightly above upper QA. It's a longer ride, but much less steep because of it. The second best ascent I've found after this one, is Olympic Ave ( a block up from Roy ). But I'm always on the lookout for a better approach, especially since my brother just got a job at the top of the hill.