I have seen lot of sailboats sailed from Europe to the States and Caribbean, they are not Hallberg Rassy. Most of them are Beneteau, Jeanneau and etc.
They don't call it the milk run for nothing. They go downwind from the European mainland to the Azores in the late spring or early summer, and then continue on - downwind again - to the Carribean. Typically undercanvassed, they get to the islands and fly home rather than try to beat their way back. Going into the North Atlantic would be a whole 'nother experience. Columbus did the same thing, but came home on the Gulf Stream. (Not that he knew what it was.)