Chiming in a bit late here, so apologies for not getting this in before you sat down and did your planning. I've done two similar trips. First one was when I was younger... we went down to San Fran and back up through Reno and onto the I-15. On that trip we took 5 days on the way down, two of which were days trips to Mount Saint Helens and the Oregon Caves National Monument. We also stopped at the Sea Lion Caves, which despite their "tourist trap" vibe were actually fairly impressive. Don't have much other advice from that one because I was pretty young and my memories have gotten a bit foggy.
Did a similar trip this summer, but only one way (flew into Seattle, rented a car, drove it down to LA and actually flew out to London from LA). Dunno if you're camping or staying at Motels/Hotels, as that can factor in to what you want to do. I was camping. Went Seattle -> Seaside OR -> Florence OR -> Trinidad CA -> San Francisco -> just past Monterrey -> Yosemite National Park -> Lone Pine CA -> Vegas (via Death Valley) -> Grand Canyon (via Hoover Dam) -> San Diego -> Los Angeles
You won't miss much if you skip the area around Seaside to hit up Portland instead. Florence was a good spot to stop for the Dunes. We stayed at a campsite in a state park just past Florence and you could walk to the dunes from your tent. Be sure to go quadding on the dunes while you're there! Trinidad is a quaint little town with a very scenic harbor, which made for a nice place to stop in the vicinity of the redwoods.
At Leggett we switched to the 101 to keep up our schedule, so I can't say much about the 1, except for the end. It's a great drive as your approaching San Francisco, if you're not afraid of heights and your passengers don't get carsick. Be sure to take the last turn of before the Golden Gate bridge too, as it's a great spot to stop for pictures.
Santa Cruz is a laid back beach town, but there's not much real interest there. Good place to stop and chill out on the beach though on the way down to Monterrey. I'd definitely include this portion in your trip because of what lies South of Monterrey. Spend a couple nights in the area, and be sure to explore Point Lobos State Reserve and Julia Pfeiffer Burns State Park. These are two lesser known gems. Point Lobos has great wildlife - tons of birds, and a few seals and sea lions as well. China Cove there has a gorgeous white beach tucked away between the rocks, as well as some caves to explore if you're feeling adventures, so don't miss it. Julia Pfeiffer Burns has a waterfall that lands right on the beach.
Unless you don't mind doubling back, it sounds like if you keep going down the coast you're going to miss out on Yosemite. That's too bad, as it's a great drive and one of the best parts of California. It's a pretty good route... go from Monterrey to Yosemite, through Yosemite to Lone Pine (neat place to stop as it's where most of the Westerns were shot and has some really funky rock formations - and if you do stop there The Pizza Factory is pretty good stuff) and then through Death Valley to Vegas. Going through Yosemite you'll probably see snow (at least I did, in May), and Lone Pine is right in front of Mt. Whitney, the highest point in the Continental US. Then within a few hours you're under sea level and it's 100 degrees out.
Don't really have to tell you about LA, as there's lots that you can do there and what you do will depend on your taste. If you're going to visit Santa Monica though, make sure you're close enough to bike/walk/jog/rollerskate to Venice. There's a huge character change as you go from one town to the other, simply because Venice rents out its sidewalk to street vendors. And while you're there, you can check out the Venice Beach Gym.
San Diego's also worth checking out. Great place to go surfing, as it gets a warm current that heats up the water. Nicer city than LA overall as well. We stayed at a campsite next to the beach at a town called Carlsbad, and there were pelicans sailing past all day. On the way up to LA, we stopped at Laguna Beach (just because) and there were dolphins jumping up out of the ocean.
Not much to say about Vegas, Hoover Dam or the Grand Canyon, as you pretty much know what you're going to get.
My recommendation: if you have time, go from Monterrey through Yosemite and Death Valley to Vegas, head down to LA from there. To keep things interesting, you can go back up via San Diego -> Phoenix -> Grand Canyon.
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