Like others, I haven't been to San Francisco since the last century. (I love saying that! LOL) My twins were born there, we stayed in the area for 3 years. The first year, however, I was homeless. I got to know a side of SF that most people don't know. If you'd like to see a less touristy side of the city, I'd recommend:
Haight-Ashbury area. This was my introduction to the extreme tolerance that California is known for. I also learned about how GREAT thrift shops and consignment stores are...nothing like what we have here in the South. These were actually shops that sold good quality, lightly used merchandise. Also, you will surely, yea most definitely, encounter a cross-section of people, beliefs and cultures.
The Mercado area. (Market street) This area is a concentration of open-air markets. There is food, food and MORE delicious food!! You'll see native culture, from the Spainard and Mexican points of view.
For a bit of reality, that all in America isn't wine and roses....the Tenderloin. It's only a few streets away from the Mercado area, but it's a totally different world. Here, you'll see the tired, poor. The wretched, the homeless........and yet......they all have a certain dignity. Here is where you will also find hope, generosity, kindness, understanding. The many good sides to humanity.
Golden Gate park. It is so very beautiful. You'll find various sub-gardens in this park. You can hug sequoias, a Japanese themed area, tunnels and green spaces. I lived here while I was pregnant and homeless. It was my safe have, my protection and my bit of sanity in a time of craziness in my life. I was here from the time I was 8 weeks pregnant, until two days before I delivered. This park saved me.
I only saw Alcatraz from across the bay. For myself, I never could understand the attraction to a place that was there because of the inhumanity of man toward man. If it was going to remain, I always thought it should have been made over into something positive. Even better, let go to return to nature.
I envy you that drive down the Coast Highway!! Be sure to check out Monterrey and Carmel. They are both beautiful!! The Napa Valley is golden, and amazing how they've been able to cultivate the vineyards out of a semi-arid valley.
Try not to be disappointed when you see Las Vegas in the daytime. After all, it (like much of Southern California) was taken from the desert. If you see it first at night, you'll be SO impressed! It's eye-catching, flashy, brilliant, full of noise and light. The casinos are easy to get lost in. I mean that on a metaphysical level. No clocks, no windows, a clinging, clanging, hodgepodge that will cause you to lose track of time. Not to mention the buffets. OMG!! Every type of cuisine one could desire! During the day, however, you see the concrete, and dust and tiredness. So, again, just try not to feel disappointed. My brother lives there, so I can ask him if there's anything or any place he'd particularly recommend, if you'd like.
Can't help you with New Orleans though. Sorry. :-)