I have been thinking about this question and after much thought I think it would take 2-3 days to cross the Channel and the time frame depends on the time of year and currents. I came to this conclusion by using the Spanish Armada crossing as an example. Ships mainly followed coast lines until the early 1400's when several inventions allowed for changes in the ships, maps, and tools needed for exploring. So, the crossing of the channel was rare in the middle ages.
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