Apple Jack
Footballguy
Don't take this the wrong way, but that sounds like a super-paranoid, terrified-of-cities take on SF. The TL and PH have no impact on an experience in SF if you don't want to go in them. Monterrey is nice and all, but outside of being on the Pacific coast it's nothing like SF.There are bad parts of SF that are right up against the other stuff. Tenderloin, Portrero Hill, etc. Just saying Monterey feels like all of the good stuff of SF without the crap parts.Wut?I would add at least a couple of days in Monterey/Carmel/Big Sur. All of the charm of SF but none of the crap.San Francisco 1-2 days, Napa for 4-days, Vegas for 3 days.That was an awesome vacation. Should have budgeted a couple of recovery days though.
Big fan of the autumn SF vacation. That's summertime there, when you are least likely to encounter the marine layer and it's when most of the killer festivals are planned. The best city in the country at it's best time of year. And you have an all-world golf course right there in the city limits in Harding Park. Best pro-tip for SF...a light dose of mushrooms and walk Golden Gate Park end to end on a sunny day, followed by sushi dinner in the Sunset.
ETA: And the TL has some of the best people watching on the planet.
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