Slow Six,
Your daughter can advise you on routes and sights to see near Seattle. As you move south you can cut over to 101 via several routes.
I haven't crossed from California into Oregon enough to know which route would be better in the winter, but there seems to be some good advice from others on that issue. Just be aware than when crossing the mountains you may be required to mount chains on your truck if the weather is bad. In that case, if it were me, I'd stay put until it cleared up. You, being a resident of the Great Frozen North (It's just a joke!), might not find it as intimidating as I would.
Hwy 101 along the Oregon coast is beautiful, with lots of medium-sized fishing villages. To get a feel for the area, check the scenery in the movie "Overboard" with Goldie Hawn. (It's a pretty good movie as well. )
After you leave Eureka, CA, 101 cuts inland, but it's still a nice drive -- much nicer than I-5. If you want to stay on the coast, which is probably the most scenic route, you'll have to cut west to hwy 1. This will eventually take you through Bodega Bay, just north of San Francisco (never called "Frisco", but "San Fran" is acceptable). Bodega bay is where Hitchcock filmed "The Birds" and also where the San Andreas fault passes out to sea to the northwest. (Notice the long slim bay, right along the fault. )
There are several ways to get through S. F. , but I agree with Brian. Unless you are worried about the traffic and city streets, I'd drive through the city. If you follow hwy 1 off the Golden Gate Bridge, you will avoid the downtown area. It will take you very near (if not right alongside) Golden Gate Park. Depending upon your timetable and inclinations, that might be worth a stop. There is the De Young art museum, a great aquarium (more later), a museum of natural history, and more!
As you go farther south along hwy 1, you will pass through Santa Cruz, where almost all of America's brussels sprouts are grown and home to a Wrigleys gum factory. (Tours for organized groups only, the last time I checked. ) A little farther along and you'll be in Castroville where almost all of America's artichokes are grown at the mouth of the Salinas river.
The Monterey Peninsula is worth some time. The Monterey Bay Aquarium (MBA) in Cannery Row is literally world famous. You may prefer it to the one in Golden Gate Park, although the MBA is limited to sealife that is found in the Monterey Bay. Carmel is just a little past Monterey. Great shopping, but expensive. There is a mission in Carmel, as well as almost every city whose name starts with "San" or "Santa".
If you decide to take 101, you'll miss some of the above, but you'll drive south through the Salinas valley. Almost all of our country's lettuce, celery, carrots, and many other vegetables come from there. There is good camping at the Pinacles Nat'l Monument just south of Salinas. You'll have to get off of 101 to get there though.
If you decide to stay on hwy 1 south of Monterey, you'll go right through Big Sur and see lots of redwoods. The biggest trees are over in Sequoia National Park (in the Sierra Nevada mountains) but those at Big Sur are still impressive. Lots of camping at Big Sur too.
Between Monterey and Big Sur you'll cross the Bixby Creek Bridge. It's the curved concrete bridge with the beautiful arch under the roadway. You'll recognize it when you see it; it's in lots of commercials and movies.
A bit farther south on hwy 1 is San Simeon, the home of Hurst Castle. Plan on spending an entire day here. William Randolph Hurst built it and it's now owned by the state of California and kept as a museum. If they still offer the upstairs and downstairs tours, take both. More camping.
Hwy 1 joins 101 just north of Santa Barbara along the coast. There used to be a refinery along this stretch of road that was the only place on the American mainland that was bombarded during WWII. A Japanese submarine surfaced and lobed a few shells from her deck gun. I don't think that there's even a marker there.
Try to find the time to visit the mission in Santa Barbara. It's the "Queen of the Missions", and the last time I was there the friars gave tours.
There are so many things to see in L. A. that books have been written. Check one out.
At the southern end of the state is San Diego, with the largest and most famous zoo in the world.
As you might imagine from all the above, I agree that I-5 through most of California is really boring, especially compared to the alternatives. The coast road will be slow, winding, and sometimes narrow, but is well worth the drive if you are not in a hurry.
You'll be one of those guys I used to pass when I'd ride from San Diego to Monterey on a fast motorcycle.
Sorry this is so long, but you asked. Happy motoring.
Loren