Sounds like a fun trip! You probably already know that October generally 
provides THE BEST weather in the Bay Area region.

Wow, for ten days, you could see a lot of stuff. I would make Marin County 
a priority. Marin Headlands, Mt. Tam, and Pt. Reyes are all amazing. Easily 
2-3 days of riding and sight-seeing, maybe more if you want to sloooooow 
down.

Not terribly sure about lodging...is camping in the mix? That opens options.

Along with all that rambling through Marin, find a way to take the ferry 
back to SF or Oakland, it is a fun diversion.

On your Rivendell HQ day, a ride up Mt. Diablo seems in order...pretty 
unique views of the East Bay on the way up, and you can see the Sierras 
from the summit on a clear day (rather rare, except when windy).

There are some fun road loops in the East Bay (Skyline/Grizzly Peak in 
Oakland/Berkeley hills, Three Bears through Briones Regional Park, Riv 
folks can direct you to more), but hard for me to say if they are really 
tourist-worthy...but they are some of my favorite rides.

Seems like Bay Area visitors are always tempted to hit Napa Valley wine 
country, but IMO those roads are really not great for cycling...very highly 
traveled, pretty much all year round these days, generally with narrow to 
non-existent shoulders. Also I find the vino-culture up there rather 
tedious and monotonous, but that's just me.

You can find some very nice, twisty, quite, shaded roads further north 
around St Helena, but you will be climbing a lot.

Oh, first weekend in October is Hardly Strictly Bluegrass in SF...if you 
are in any way into music, you will find something you like...all free, of 
course...and packed...but a pretty special social phenomenon.

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