Another cocktail bar we enjoy in San Jose is Paper Plane https://www.paperplanesj.com/ - the owners are involved in a number of bars and restaurants in San Jose including MiniBoss and Alter Ego.
Paper Plane isn’t really an intimate cocktail bar but has more a large floor plan with several booths and tables but a place at the bar tends to be best option. The quality of cocktails is high and often quite creative. We also like their approach of a cocktail menu map which visually shows you the different types/flavor profiles of cocktails on their extensive menu
Outer Sunset isn’t really a hotspot for cocktails but has a few very good cocktail bars which fly a bit under the radar. One of these places is Lost & Found https://www.lostandfoundbarsf.com/ on Taraval (which also has the advantage of easy parking). Outer Sunset has quite a number of different Asian restaurants and so it is no surprise that some of their very good cocktails tend to have sometimes an “Asian” spin. Normally Lost & Found had also a good kitchen open late but it was closed on that night
Speaking of Outer Sunset cocktail bars on Taraval, I was super impressed with White Cap when I went a year or so ago. My feeling was that it’s in the same league as ABV, PCH, Trick Dog, and my distant memories of Haberdasher and Paper Plane from a decade ago.
I really like White Cap and their Surfer on Acid signature cocktail is really nice. Feels overall like a neighborhood bar but with much better cocktails than you would expect