(caveat: i haven't done this ride exactly, but have ridden from north
of santa rosa through napa to vallejo, and have done a lot of riding
in marin. i would also be eager to hear input from santa rosa/sonoma
locals!)

i'd suggest you take the ferry (either to larkspur or vallejo) to get
started.  only problem is that to take the ferry to either of those
spots you can't go from oakland, but must start in SF. since you seem
willing to BART you could always start by doing that. you can also
take the ferry from jack london to the ferry building and sf and
transfer (check http://www.eastbayferry.com/ for schedules etc).

from vallejo...well, you'd have to ride along hwy 29 to get to napa,
and it's not very pleasant. wide shoulder but trafficky. (the bay
trail is not yet finished between napa and vallejo, though they are
making progress). once in napa, the easiest route would probably be
via the silverado trail, then cut over to the west at st helena and go
into santa rosa via spring mountain/st helena/calistoga. steep,
narrow.
you could also devise a route that got you to hwy 12 without having to
go on the busiest roads, but you'd likely have to do a stint along 12
or 121 at some point, and on the weekends these roads are congested
with drivers and would not be fun. also, since many tourists are in
the area to drink wine, i would try to avoid riding them after noon if
you must ride them at all.

via marin - little more wander-y, but you could take the ferry to
larkspur, head west along sir francis drake past fairfax, turn towards
to nicasio valley road (just past san geronimo), then turn right on
petaluma-point reyes road...then, when you get to petaluma, head north
via either stony point (west of 101) or redwood/petaluma hill road
(east of 101). these are probably the most direct if semi-trafficky
options, so ymmv depending.

(after i wrote this i checked google maps' bike option - google
suggests the petaluma hill route - 65 miles, 6.5 hours. napa route
adds 20 miles. good luck!)

ian

On Aug 3, 11:14 am, CR Masterson <crmaster...@gmail.com> wrote:
> I'm happy to BART across the bay, head up through Marin.  Or any other
> way you have fallen in love with.  It would be nice avoid huge trucks,
> mondo hills and traveling way out of the way as much as possible.
> Thanks.

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