I'm planning to take my struggling, recovering substance abuser sister to a winery for her birthday.
Are you still planning to do this knowing your sister has a history of substance abuse?
I'm going to, so I can have some fun.
Exposing your sister to another substance when she has issues with that is a recipe for disaster. If you want to spend time with your sister you should find other things to do that don't involve alcohol or other substances. If you expose her to alcohol she could lose all progress in her recovery.
So I can't drink because she's a recovering addict?
Well, you can drink if you're not an alcoholic, and you can do that without your sister being there with you so that you don't expose her to other addictions. Your sister is going through a lot and it is your job to be respectful towards her by making sure she stays clean.