San Diego fishing trip and then road trip to San Francisco

So a couple of buddies and I are heading to San Diego next week, fishing for a few days, and then taking our time driving to San Francisco and flying back. Only one of us has ever been out there before, and it's been probably 20 years since he was there last. We're flying in Thursday night and we've got a boat rented for Friday, Saturday, and possibly Monday if we're feeling up to it. It's a 23' boat that we'll be captaining, leaving out of the Dana Landing Marina, I believe it's called. Tuesday morning we'll be renting a car and heading up to San Francisco over the next few days, aiming for the most scenic route possible. Our flight doesn't leave from San Francisco until later on in the day on Friday, so we'll have plenty of time to stop along the way. One thing we do have to include is a drive to the Redwood Forest so my buddy can scatter his parents' ashes. I've gotten a few suggestions from other friends/family on what to do while we're out there, but I figure it couldn't hurt to have more input. What I'm really wondering is--

1) We fish all the time here in Florida, but we're on the gulf side and it barely gets deeper than 50 feet out here. Is it feasible to think that we'll be able to take a 23' fishing boat out on to the pacific and land some monster fish, or is that just a pipe dream?

2) We will also be bringing barely any fishing gear besides just a few basic tackle boxes with sinkers/planers/hooks/etc... and no rods or reels with us. Are there any good tackle shops nearby that will rent us gear for a few days without charging us an arm and a leg?

3) What kind of techniques should we be expecting to use out there? I've tried googling, but haven't really been able to come up with much usable info. Are there any wrecks/reefs/particular spots we should be focusing on hitting?

4) I just read that this is gray whale migration season and we'd love to catch a glimpse of a whale or two. Is there anything special we need to know about, I guess it would be whale watching? I.e. Where to see them, how to not get capsized by them, etc...

5) Once we're all fished out, where should we head in San Diego before we leave, or at night, whenever?

6) We're aiming to mostly drive up the coast, what are the can't-miss spots that we should stop at on our way north?

7) Once in San Francisco, what kind of things should we be looking to do or see? Is Alcatraz worth it?

Sorry for the long-winded post, but the trip was sprung on me at the last moment and I really want to get the most bang for my buck, so to speak, especially with the fishing. Thank you in advance for any insights.

Thanks Adam, some great tips in there. I hadn't even thought of Big Sur, but it's definitely on the list now. None of us are into wangs and it's probably going to be a pretty tame trip since we're trying to get so much done in a little time we'll probably end up sober most of the trip. Maybe a brothel, but we're all married or close to it, so probably wouldn't be worth the effort.

Thanks for the heads up about Alcatraz, I had no idea. We'll definitely make sure to do that once we know what day(s) we'll be up that way. And the google image search for Marin headlands looks pretty awesome. Thank you guys again for the recommendations, we're all getting pretty excited, especially about the fishing and the scenery.

Well now I'm definitely in for the headlands and hipster hunting. That sounds badass. We're planning on the 1/101 up for the scenery. We figure it's worth the few extra hours not to be stuck inland, and not to smell cow shit either. Carmel was one of the stops on our list, especially since one of the guys going with us is a big golfer and Pebble Beach is right there apparently. Is it worth wandering over that way to check it out if we're not going to be playing a round? Thanks again.

I've actually been going back and forth on the aquarium idea. It seems like a great idea, but we are coming from Florida so usually what we end up seeing in aquariums is stuff we end up running over on the way out to fish here anyway. Side note: One of the main docks I use shares their dock with that bullshit winter the dolphin tour and the bastards think they own the waters and get in everyone's damn way because they were in a crappy movie. How does the aquarium stack up against, say, the aquarium at Mandalay Bay in Vegas? That's one of the biggest I can recall going to lately and it was pretty decent. Along those same lines, would the San Diego zoo be worth it? I was thinking yes, but then they pointed out that we can go to Busch Gardens any time we want and none of us could even remember the last time we went there.