If you want to taste multiple wines at dinner, and wish to have them simultaneously instead of consecutively over the course of the meal, that’s completely fine. Just make sure you clearly explain your game plan to the server or somm.
Let them know that you wish to order a few bottles of wine that you’d like to taste side by side with separate glasses for each. Allow them to decide which glasses they bring — don’t demand the largest glasses they have; your table may not have room. Plus, it is probably a good idea to make sure that you have the appropriate table space to accommodate the glasses and your food before you even begin this process. This would also be the appropriate time to ask for a spit bucket if you plan to taste more wine than you want to consume. Most restaurants will either have one on hand or at least bring you a mixing tin from the bar to serve the purpose.
The only faux pas you could make in this situation would be to bring multiple bottles of your own wine and expect to open them all simultaneously without calling the restaurant first to check and make sure that’s OK. Many places have a policy regarding how many bottles they allow you to pay a corkage fee for, so make sure you don’t exceed the limit. And by all means, please tip well.
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