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@middleofnowhere
Round the Isle of Wight following the Cycle Island Route: http://www.visitisleofwight.co.uk/dbimgs/RTICycleMapNew.pdf
We will aim to get the last ferry from Portsmouth Harbour to Ryde which leaves at 22.45. We will then waste a bit of time, possibly by sitting in the King Lud, possibly another pub depending on how busy they are, and set off in a clockwise direction. The ride will have to be slow enough to arrive at the floating bridge in Cowes after it starts up at 5.00
There are trains from Waterloo and Victoria, the ones from Victoria seem to be quite a bit cheaper. The viable trains are:
Victoria 20.05 arr 22.05
Waterloo 20.30 arr 22.02
There is a later train from Waterloo that gets in at 22.37 which might be cutting things a bit fine.
https://ridewithgps.com/routes/665774