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Please comment on proposed US itinerary

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Hello US Friends,
this is the itinerary I would like to suggest to my family for a long overdue trip to the States. But before I do, I wanted to get some advice from the locals.
We are travelling from Italy, kids are in their 20's - one works in the wine industry and we all like eating, drinking, cities, walking, driving....
Here goes:
Rome -San Francisco 2/3 days in the city
3 days Driving round Napa Valley
Head South stopping one night Carmel/Monterey
One night St Louis Obispo
2 nights L.A:
2 nights San Diego
Fly to Los Cabos (San Lucas or San José?) for 4 nights
Fly to Houston (1 night to visit old friend)
Fly to New York - 3 nights
Day 21 fly back to Rome
My questions are...is it worth stopping in San Diego? We have never been there but we have been to L.A.
Is Los Cabos fun? Worth the trip in February? Presumably too cold to swim. Is it an interesting place to visit? We don't really go for resorts or mega hotels but we did want to go somewhere warm with a good vibe. (will also post this on Mexico forum)
Any suggestions for things to do/see/eat on this trip.
Any advice greatly appreciated.
Thanks!

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