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having ridden quite a lot in cornwall (my mum lives on the lizard) i wouldn't recommend brakeless. a lot of the hills are 25% and super windy and narrow, not to mention that locals drive pretty fast on them!
although you could probably avoid a lot of the hills, but to do so would involve riding on busier roads, which would be a shame as the lanes in cornwall are spectacular.
I'm thinking about doing JOGLE fixed/brakeless this Summer. I did London to Cornwall last year on a TT bike so I know the hills in the SW are tough but I reckon it should be OK - does anyone have experience of this??