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I highly recommend the Crosstown Trail, a grassroots-developed 17-mile hiking route across San Francisco that strings together existing paths through parks, urban greenways, stairs, and the bits of road needed to connect them.
There's an associated bike route that combines parts of that trail with parallel road routes where it would be impractical to ride (though even this route also includes some carry-your-bike staircases and narrow dirt paths). Just imagine, you can experience all of this within the city limits:
I rode this route twice this year with friends, details continue below:
There's an overview of the trail as well and maps and cuesheets on the official site, and I especially like these maps of both the hiking and biking versions of the trail (consult the legend to see which is which). In case that link breaks in the future, I've cloned a ridewithgps route I found and have started to add markers for food, water, viewpoints to climb, and other stops we found along the way. Even with maps, we had to use our eyes when navigating-- some trails and turns are not obviously named, but there are some signs and hints from the contours of the land...
We split the riding over two days (months apart) to have plenty of time to sightsee along the way-- there are a lot of interesting things to look at if you're going slow. We also needed time to ride to and from BART, get lunch, and walk our bikes on a few steeper / rougher dirt sections (we were all riding our "everyday" bikes). On narrow trails whenever we encountered people (which we often did midday around Laguna Honda, but much less when we rode it a second time on a Sunday morning) we dismounted to be polite and turned it into a walk in the woods.
For our first "tour", we met at the Ferry Building, took a twisty shoreline-parks route down to Candlestick Point (avoiding 3rd Street completely), and rode the first 2/3 of the trail to Golden Gate Park, then stopped for lunch and detoured to visit Sunset Dunes park. This was our route (currently just a screenshot and not a clickable map, but see the RWGPS link above):
This was about 33 miles, and took us most of the day, about 7.5 hours(!) with all our stops and exploration.
The second time we toured it we started at Glen Park BART, rode the trail to Lands' End, then toured Sunset Dunes and rambled back to the Mission, something like this:
This was about 22 miles and my phone says we spent 6 hours together (though only 3 hours actually moving) when you add in birdwatching, climbing stairs to scenic viewpoints, and a casual lunch.
But enough about the maps, here are some more photos to convey the vibe. Riding from the Embarcadero down to Candlestick Point:
A new-to-me highlight was the Vistacion Valley Greenway-- multiple mid-block paved trails past community gardens and murals:
McLaren park views, a few staircases, and one steep bit of hill:
Between parks, a bridge over a highway:
Dirt trails near Laguna Honda Hospital:
Some of the later trails near Golden Gate Park and approaching Lands' End:
And some panoramic views along the way:
I loved both of these days as ways to explore the city-- I'd bike (or walk) this again in a heartbeat.