As far as can tell, this has to be done in a single playthrough.
Every venue in hell has its own assortment of drinks at the bar, usually 4-5 different drinks.
Be sure to order all the drinks and take a sip, so it counts.
You can't go back to some places making some drinks and the achievement missable.
There are more than 20 drinks to be had, regardless of the path you choose.