Hi FC and welcome. So, are you bringing your own bike over or buying something over here? There's plenty of stuff in the archives here about doing the latter but if you're starting in Ireland in winter I hope you like rain!
If, as you say, it's your first time out of the US you might find riding on the left an interesting diversion from the water but normal service will be resumed as soon as you hit France or any of the other mainland countries.
Most of the decent riding conditions are likely to be in the south of Europe - now(ish) is a popular time of year for e.g. Morocco. Winter biking in northern Europe tends towards the expedition type of trip - camping in a snowdrift type bike rallies etc (for example - https://www.bvdm.de/index.php?id=47&lang=3 ).
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