Good to see the forum, up and running again. How did the CW & YWW go, Harland. I'm planning to walk the Cleveland Way in 4 weeks time and always a good walk to do.
I walked the first 4 days that most guide books show in 2 days which was about right for me. I stayed at Helmsley youth hostel the night before then stayed at Osmotherley the first night then the YHA Kildale Camping Barn the second night. Whilst the time walking was about right in those first 2 days I must say that Osmotherley to Kildale did test me as I do weigh some 16 stone being 6' 4" tall. The rest of the Cleveland Way was roughly as per the guide book. As you have walked it before you will know that the signage is first class.
A different walk than my previous ones albeit that I have walked the SWCP before but the walk from Saltburn to Filey was different but enjoyable and a bit easier than the north coast of the SWCP. I didn't know the east coast very well beforehand so it was all fairly new to me but I did enjoy it. Not many fellow walkers apart from day walkers until you get to Robin Hood's Bay where there were lots of people completing the C2C. There was a bit of sea fret that did reduce my enjoyment a bit but when it cleared the sun was red hot! Never having been there before I even enjoyed walking along Scarborough sea front.
The part of my walk that I enjoyed far more than I expected was the Wolds Way, walking in, around and over the dry valleys was a real pleasure. Thixendale was a real delight and a wonderful place to stay the night. I did the walk from Filey to Hessle whilst I met a few people coming the other way I didn't meet anyone going my way. Nobody could understand why I was walking it in that direction notwithstanding that they knew I had walked the CW first finishing at Filey.
If there is anything specific you want to know then let me know.