I will be taking my husband on a surprise trip to San Jose to see his brother in October. I would really like to go up to San Francisco a few times and check out the sights (we have never been there) Is it smarter for us to drive there ourselves.. Since I have read parking is hard to find and $$$(or is that just overnight parking) or take a train?

Is it doable: to stay a day or 2 with his brother, then move up to San Francisco and stay here?

When we go to SF for the day from San Jose, we either take Caltrain or BART.

Caltrain is a heavy rail line that runs from Gilroy to SF. The trip from SJ to SF takes about an hour and is around $10/person, round trip. Trains run fairly frequently and the terminal station in SF is downtown. From there you can walk or take public transportation to most place in SF.

BART is the other option. It doesn't go to SJ, so you have to drive to a station. We either drive to the Fremont or Colma station and take BART from there. BART also goes downtown - actually runs right under Market St, which is the main downtown street - so that is very convinient.

Occasionally we will drive into SF, but generally only if we are going for a specific thing and then back out again.

Parking is expensive and I believe the city has just raised the parking rates, and driving can be confusing.

Parking is expensive in the area, but not prohibitive if you have a car. There is a train, but it will be slower. I would go by car as you will want to drive over the Golden Gate Bridge and explore the area. You cannot do this on a train.

Pretty sure you'd be better taking trains and taxis.
Figure the cost of car rental, gas used, parking, time for navigation.

I prefer to let a pro drive. The overriding reason is that the grief expense is lower for me.

How long is the total trip? You say you want to go to SF a "few times". No matter how you do it the trip is NOT fast/easy - especially if you are traveling north into SF during the morning commute and south to SJ during the evening commute.

Instead of traveling up to SF multiple times, it would be much better to stay a while in SJ and then go up to SF and stay there for the rest of your trip. You would not need a car to tour around SF for a few days.

Caltrain now has the "Baby Bullet" service during peak hours, where you can get from San Jose Diridon to San Francisco Caltrain station in 55 minutes. From SF Caltrain, you can get on the Metro Line N to Downtown, or transfer in downtown to the historic streetcar lines to Fisherman's Wharf.

If you don't mind the hotel expense, the suggestion to overnight in San Francisco is a good one.

The high cost of parking is only in the certain areas, like downtown SF. Otherwise, parking is fairly reasonable, e.g., the huge parking garage across from the Metreon offers pretty good prices for a centrally located garage. In other places, free (gasp!) parking can be found in SF. For example, at the top (northend) of Van Ness Street, you can park for free for 4 hours. Over in the Mission District, I routinely find free parking, e.g., on Guerrero Street.

Driving the streets of San Francisco is another matter. If you take a car, you'll want to park it. You do not want to be stuck in a car on a one-way street crawling along like a snail. Your vacation is not long enough for such waste of time!

As mentioned, a car will give you greater flexibility - Golden Gate Bridge, Twin Peaks, Palace of the Legion of Honor, etc. You'll want to drive around San Francisco at least one day. Pick a weekend day if at all possible.

So, here's my suggestion: Drive up to SF one day to see the sights that would otherwise be hard to see by public transportation. The other days, either take public transportation back and forth OR stay overnight in SF.

Good luck! And maybe your brother-in-law could do the driving!

Easytraveler nailed it, IMHO.