Yes, I have the "Trucker's" tan too. And, my face is bright red. I am going to bring a radio next time. We were confused by all the stops. Overall, it was a good drive.
How about a run down 880S/17S to Black Road? We can take Black up to Skline. At skline and hwy 9, we can go south on hwy 9 to Santa Cruz. The club could hit the boardwalk. Then, it's just a drive up 17N/880N to get back.
Alternatively, we could take Skyline to 92 and then come back on 280 or 101.