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@Sam
I've done right around the coastline a couple of times, it is pretty hilly on the eastern side. I plotted a route for it on Bikely which a) looks to be down at the mo, and b) I don't use any more. Basically I just stuck to the closest road to the sea I could all the way round. Works out at around 65 miles, including a trip down to the Needles lighthouse, and using the chain ferry in Cowes.