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@Buffalo_Bill
Luggage - personally I wouldn't use handle-bar mounted stuff (apart from a map-holder which is absolutely essential!) or anything on the front-wheel. Have a look at the Carradice under-saddle bags. If you are serious about travelling light, then I think those might do for you - and they won't affect the front-end handling in the way that h/bar bags do.
+2 F1 Mille shorts. I was wearing those for the tour, with a cheaper pair over the top, but still ended up hurting like hell.
I wouldn't bother riding to Dover. To get a nice route, we ended up going Sevenoaks and south of Ashford, looping around over the A20 and coming in through the North Downs. 170k or something.