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Many sites state that bottles of vintage port should be stored on their side, like wine, in order to prevent the cork from drying out. However, at the bottle shop, bottles are standing upright on the shelves to display themselves more attractively.

We don't know how long the bottle has been standing upright, and it could have dried out the cork, and then do bad things to the port once layed on its side again. Once a bottle comes out of the cellars and is put upright on a shelf for let's say a couple of months or a year, is it advisable to lay the bottle down in storage again?

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It is generally preferred to store wine on it's side, but I think the climate the wine is stored is even more important. Generally, a wine like a vintage port, will spend only a short part of it's lifetime on a shelf in a store. I really doubt that even a year or two will dry out the cork unless the humidity levels are very low. One way to check if the ullage level is low. Ideally, any wine that you want to age should be kept on it's side, in a dark, cool location. Moving the wine upright and back once a years is not ideal. Will it hurt the Port? I really doubt it. Port is pretty sturdy stuff since it's fortified. I wouldn't worry too much about it. The age is also a factor. If it's 10 years old, that's nothing for a port. If it's 50 years old, then I start to worry about it...

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