If you ever go to Los Gatos, San Jose’s poshest sub-city, make sure that you have a designated driver or enough money on your card for an Uber. The town is absolutely beautiful and as a result absolutely overflowing with pretentious house wives and some of the South Bay’s elite. As a result, drinking in at least one of the town’s fine establishment to get through the conceit is strongly encouraged.
If you’re looking to get shitty drunk and dance I recommend Mt. Charlie’s. If you want to get dolled up and go somewhere where people stand around eye fucking each other, go to Los Gatos Bar and Grill. If you are on a first date, go to any one of the excellent restaurants and stop by Carnations for a drink after. But if you want a jukebox, a stiff drink, and to pour your own Kamikazi’s you should go to the Black Watch.
The Black Watch is as close of a place as you’ll find to a dive-bar in Los Gatos, their drinks are straight and the crowd is comprised mostly of blue-collar Los Gat-ians and a few local musicians. I like it as much as C.B. Hannigans around the corner, where I recommend going if you want to dine well and then continue drinking heavily after the dining room closes.
But whatever you do, when you come to Los Gatos, make sure to have yourself a drink.