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Do you need to stay in Union Square? I recommend not staying there, or surrounding neighborhoods.
Well, I’m thinking of staying at this historic hotel called The Beacon Grand. It’s gorgeous. But of course we are venturing out of Union Square. Just want to be safe but also have fun.
Most hotels are in Union Square so I don’t think OP can easily avoid the area. It’s SF - any bars are gay friendly. I don’t enjoy being in straight places when drinking out so my recommendation is skewed. I personally like Lobby Bar. It’s attached to a neighborhood hotel in the Castro and is often bustling without being crazy. Not sure if it’s upscale enough for you though.
Horsefeather, trick dog, last rites, whitechapel
I lived in sf for 9 years before moving back to ny a couple years ago. Go to blackbird! It’s a bit more upscale but gay friendly crowd. They make craft cocktails and it’s a nice vibe.
Castro is fun but more of a get wasted and dance kind of place.