Hi
It's about 350 miles as the crow flies. I have driven both ways in January and had good weather. California is known for it's winter sunshine and people sunbathe on beaches in December in Los Angeles. It is not impossible but very rare to get icy roads.
Do have a look around San Francisco before leaving. A fair number of places to see. A car can be handy there. They do tow if not properly parked. I went to Chinatown there one quiet Sunday morning and the place was packed with people.
Lots of nice towns and places to drop in on the way. I could name some I liked but you may not. If I were you I would invest in a California Travel Guide from Lonely Planet. And a good road map rather than the little thing the hire company gives you.
Check out your car before you leave. I had one where I just touched the brakes and the car stopped dead from over 10 mph and had I not had my seat belt on, I would have hit the window with my face. Another time on my first night I found the headlights (searchlights) were on full beam and I had to pull over and find out how to dip them (there was a button on the floor).
Do take out Collision Damage Waiver (CDW). It's expensive but having an accident can be a lot more expensive. Personal insurance too. In the unlikely event of a serious hospital visit there for any reason, you don't want to take out a second mortgage to pay for it.
Right hand drive is no trouble. Remember, take your time. It is when hurrying that trouble occurs. Also early morning when you first pull out. Instinct says the wrong side of the road.
Observe the speed limit as there are cops about. If you see a motorbike on a motorway, it is probably a cop. If a cop pulls you over for any reason, hands on the steering wheel till he says otherwise.
Don't take the scenic coast road. Lots and lots and lots of sharp twists and turns for dozens of miles. I still remember a sign "Sharp bends for the next 46 miles". I just beat it before it got dark.
Accommodation is expensive if you turn up but can be booked a lot cheaper on the internet, if you can do so, with internet cafes.
LA is a BIG place. I had to drive through it once and I hit the City Limits and 85 miles later, I'm still in LA. People generally travel by motorway any distance there, as normal roads take far too long.
Sign posts will not always give destinations but sometimes compass points so you have to know what direction you are driving in. Don't overtake a stationary school bus letting kids on or off unless you want a ticket.
It is tempting to dress up for such a holiday but that will label you as tourists in some areas. Keep some money handy (maybe $60 in small notes) and the rest hidden and if you are held up, hand it over and do not do anything (the guy may have a gun or knife). Use common sense, especially about going out at night. I've spent well over a year in America in various places at various times and never been held up, but it can happen.
After 2 weeks there you'll wish you had booked another week or two instead of going home to cold weather.
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