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(Here's my MotionBased GPS data, for those of you that like to skip ahead.)
We started from SF, went down Skyline (Hwy 35), and cut over to Highway 1 on Sharp Park Road. (Which, by the way, has a bike lane for the first hundred yards - then you're in the lane with traffic and need to keep pace with it to stay safe; fortunately the speed limit's about 30 and it's downhill.) That dropped us into Pacifica, where we followed the beach for a bit and watched the despondent surfers waiting for waves. Then we got to "http://maps.google.com/?ie=UTF8&ll=37.58635,-122.507987&spn=0.014487,0.043945&z=15">here, just south of Pacifica, where the road narrows to not-quite-one-lane-in-each-direction with negative shoulder (gravel leaks on the road, as opposed to there being excess pavement on the other side of the white line). It's twisty and the traffic is fast and it's pretty significantly uphill. I must have driven this road dozens of times, but somehow did not remember this four mile stretch. After an eternity we made it to the top, with a nice view of the ocean. The way down the other side is more complicated: instead of going 6 mph and keeping to the "mountain-side" edge of the road, you're going 25 mph on the "cliff-side" edge of the road. Cars that would have been able to pass you going up are now stuck behind you going down, with predictable displays of unhappiness. (It's a freaking construction zone - it's not safe for them to be going faster either.)
Anyway, we got to the bottom in one piece and decided we were definitely not biking back up that stretch of highway. The remaining descent into Half Moon Bay is very pleasant, with a wide shoulder and expansive ocean views. From Half Moon Bay, tere's only one other choice for getting back to SF: go up and over Hwy 92, then back on Skyline. So, after a sandwich, we headed up the 92. I remember this being ridiculously steep from the last time (5 years ago?) I tried it, so I stayed in a comfortable cadence in a lower gear the whole way, expecting it to get steeper. But I think it's a pretty even 7% grade for the whole way. Drafted off a motorcycle group on the way down. Back up Skyline was pretty uneventful, until we got lost and cranky in Daly City (a maze of twisty passages, all alike).
Total ride: 60+ miles, 6800 vertical feet.
Having learned my lesson, and still wanting to see what was further south, the next weekend I drove the car to Half Moon Bay and rode the bike south starting there. (This was a solo ride, as my better half was sleeping off the previous night's festivities.)
South from Half Moon Bay, Hwy 1 is almost-imperceptibly uphill for a while, then is a series of rolling hills into Pescadero. I assume this would be beautiful country on a nicer day, but the sky and ocean were both slate-gray and the temperature was hovering around 50F. The surf looked like crap but there were still some diehard folks out there. I didn't see many other cyclists.
Pescadero appears to have no actual, um, restaurants or anything, so I nibbled at the gas station and watched tourists complain about the price of gas. Then I took Stage Road north towards San Gregorio, which has some hills taller than "rolling" but with a similar effect of "climb 300 feet, descend 300 feet, repeat, repeat". There's a general store in San Gregorio with a bike rack out front and a sign that asks cyclists to take off their shoes before entering. I was going to lock up my bike before going in, but the motorcyclists having a heated debate out front assured me that the last thing anybody would steal around here is a bike. I went in and got a coke. Sure enough, nobody stole my bike, although when I came back a dog was... never mind.
Stage Road meets back up with Hwy 1 a few miles later, and it's all downhill back into Half Moon Bay. At this point I suddenly felt the need to make creme brulee that evening, so I bought a blowtorch from the Target and drove home. 30 miles, 2000-ish vertical feet. (MotionBased data)