I think that would be a challanging, but very diverse and scenic ride...you'll get to see some of California's best, from big city San Francisco to the legendary Big Sur and Yosemite.
San Francisco has a nice hostel if you're on a budget--but get there early, it books up fast. Don't forget to visit a couple of quaint towns--Monterey and Santa Cruz-- on your way down to Big Sur. Monterey has a world class aquarium and a great detour called "The 17 Mile Drive" that passes by the famous "Lone Cypress" tree. Santa Cruz is a surfing/college town that oozes an alternative laid-back atmosphere.
Camping is plentiful around the Big Sur area. The coast ride has lots of moderate ups and downs, but no long climbs or passes. Most of the road is narrow and winding, but very manageable. It's a biker frendly area...you'll have plenty of company.
I can't offer any advice as you travel inland to San Luis Obispo (although it's another nice bike friendly college town set amongst rolling hills.) Crossing the Central Valley to get to the Sierras could be a letdown. When I biked through that area in early summer, it was unbearably hot and humid. Towns are few and far between, so you have to be pretty self-sufficient. Not much scenery either.
Getting to Yosemite will be dangerous but rewarding--no shoulder, unsuspecting tourists in RV's, blind corners, steep climbs. But once you reach the summit and zoom downhill through the 1/2 mile long tunnel to have all of Yosemite Valley open up before your eyes, you'll know it was worth it. After your long climb, you'll want to spend at least a few days resting, hiking and taking in the sights.
IMHO, your ride takes in a lot for a 2 week trip! If you want to relax a little, an alternative would be to stick to the coast--from Oregon to Big Sur or maybe SF to the Mexican border?
If I can be of any further help, let me know.
best regards,
Ron
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(take out the x's)