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Ah, another psychopath like me! Yes everything was pre-booked about 6 months in advance. I even had a spreadsheet of all the details under the clear pocket on my rando bag - romantic I know. Slight gamble because if one of the ferries couldn't run then everything's messed up, but we passed literally hundreds of B&B's and I'd guess 80% showed 'full' so glad we did.
Regarding the shorts, they were actually an old paid of (Wrangler?) trousers. Like most of the shorts I wear nowadays when they get holes in the knees they're given another lease of life. Sorry that's probably not very useful answer!
Love a chilled tour. How did you work out the accommodation for the airbnbs? Pre planned it all out like a psychopath (me) or took it free and easy with last minute booking?
Also I like your shorts, where'd you get them if you don't mind me asking?