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Mark Beaumont did it clockwise - https://www.komoot.com/collection/1120567/-around-britain (as did @TheBonk from this parish, if I remember right. I remember a lot of content involving headwinds along the south coast, in fact)
honk
I would be inclined to go clockwise to get the wind all the way up the west coast, which must be far longer, and just suck it up on the south coast.