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The wind blows to every direction on the compass, and from every direction on God's green earth. The one place where there is definitely a prevailing wind on which you can rely is the Pacific coast bicycle route. Sure you may get some side winds now and again. The prevailing goes from north to south and it can be a stiff prevailing wind.
I always carry a mini-pump. One advantage is that you get a great upper body workout using them, which helps to balance out all the legwork of cycling. JK. I bring them but hate using them because I'm at the age (73) where I don't really want that extra workout in a crunched over position. Instant backache!
A great workout? Do you get a flat every day? That's the only way it would be a "good" workout. I average one flat every 6 months, so not much of a workout there going on.
I chose to ride through SF from Samuel Taylor State Park to Half Moon Bay, for the reasons you stated. I didn't want to pay SF prices. There's a nice campground at Half Moon Bay, but watch out for the raccoons there.