I'm glad that @ChickenRacer answered you and I too don't have the Square answers, but it also sounds like you're looking for someone with some business experience, specifically in your field, to give you some answers on the physical operations of your business, not the Square side. Would that be correct? If not, by all means ignore my ramblings below, lol...
While I'm not in your field, I can make a couple suggestions. I haven't looked up your location to see where you are, but here in MT, tap rooms are extremely popular. I can't speak to specifics for your business, but just in general marketing I would do both - tasting and the bottle. I would calculate the cost of the individual tasting, based on the price per ounce from the bottle. Determine how many ounces is the tasting, to calculate the price, the add your markup, just as a starting point.
Another suggestion that I would make is, if you haven't already, check out the other tasting rooms in your area. See how they are charging and how they are serving. Compare their offerings and prices to what you plan to do. Can you do something similar and competitive or are you completely different? Is the difference between you and then going to be appealing to your demographics?
If this didn't help, please be sure and let me know so that your post will keep popping up and we can get more answers for you!
Owner/Business Manager
Arctic Heat
R&C Property Management
Event Planner/Business Trainer
Member - Women in HVACR
Member - NAWIC; Mentorship Chair for MT Chapter
Square Champions Expert
