Ken and I are heading to CSS in August. We love wine! We want to bring some of our favorite bottles from home. Does anyone know if there are any issues getting wine through customs? Also, would we be allowed to bring our own wine to a restaurant there and have them open it for us? Would they charge a corkage fee?
I don't know about getting wine through customs in Jamaica. A phone call or some internet research may clear that up.
Here is my feeling on the second part of your post. If you have a very special bottle of wine, say an anniversary bottle or unique gift bottle you want to drink to make a meal extra personal, then that is one thing. If you explain ahead of time to the senior waiter about this my guess is that they would accommodate you with your needs.
However, to repeat this process more than once may well be taken as a bit of an insult as to what is proudly offered by the very wonderful Sans Souci staff. It is my opinion that the wine offered at no extra charge at CSS is rather ordinary and as a wine geek I wish there was more of a selection. But the wine is fine and goes well with the amazing food you will be served.
One can not expect truly upscale wines to be served "all you can drink" at an all-inclusive without someone paying the piper some where along the way. There is an upcharge list of wines available with some good selections. It would be nice to have a few other wines available at a more modest up-charge, but one has to remember that only so many service options and complexities can be allowed in a restaurant.
An option for you if you really want to carry some wine to CSS would be to get room service and drink them in your suite. Room service at CSS is one of its special features and you should order it at least once during your stay. A Couples dinner on your balcony is very romantic!
Personally, I would leave the wine at home, just relax and have a wonderful time at CSS. Your wine won't enjoy the ride in baggage anyway.