San Diego to Portland OR X-mas to New years
 

I have time off, airfare flexibility to and from west coast. We are planning on San Diego and driving to Portland. I have up to 10 days and want to have fun along the way, not a hard drive along I 5. Thoughts?

Can you break down the ten days? How many in San Diego, how many in Portland?

In late December I-5 is seriously annoying as you can have fog in the California central valley, snow in the Siskiyous, and icy roads in southern Oregon - at a minimum.

Following the coast, you can count on wet conditions anywhere north of San Francisco. Plus, of course, daylight will be very short.

I personally would follow US 101 all the way to Reedsport in Oregon, then cut across to I-5 and north to Portland. Here's a five day/four night route with the overnight points highlighted: https://goo.gl/maps/jYGBythdRcy . Highlights will be Santa Barbara, San Francisco, the redwoods, and the southern Oregon coast.

What do you want out of this trip? A road trip, or sightseeing? It really isn't the best time of year (understatement) to be planning a road trip in Northern CA/OR. You could be lucky -- or you could have 10 straight days of fog/rain/snow (and rental cars usually do not allow snow chains)

Plus 10 days is not very long if you want any time at all IN San Diego, Portland, and/or San Francisco.

If you mainly want SD and Portland -- then spend 5-ish days in SoCal, fly to Portland and spend 4+ days in that area.

We've done the Benson Hotel in Portland for NYE. Lots of fun.

I'd probably do what Janis suggests. 10 days really isn't long enough for the driving when the roads may be bad. And that period between Christmas and NY is when they are frequently really bad in OR. I drive I5 in OR at that time of year frequently and if it isn't icy, it's foggy or torrential rain. Just no fun.

I would fly!

The roads could be fine or you could be sitting on a mountain pass in a snow or ice storm
Several years ago there was a big ice storm the week of Christmas.
It took me 10 hours to get from PDX to Eugene. Sat all night on 205.