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I've thought about doing something similar but never been back!
I'd recommend heading to Cork, doing some of the coastal roads to Baltimore. There are lots of islands, I took a ferry to Cape Clear, which was great but then got the ferry to Schull. This part of Cork is great.
Healy Pass in Cork would be a must do (again) for me. Then the Beara / ring of Kerry peninsula. The inland roads (Balaghbeema pass I think?) Are great, and there are some options. I'd make time to visit the Skellig island even if it is a tourist attraction, it's quite something imho.
Then you could do Dingle although I found the traffic there some of the worst in Ireland. But I've heard it's scenic. Then back from Killarney or Tralee?
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I watched a slightly irritating video from GCN or Rapha with Kristian House about winter clothing a couple of years ago. It actually changed how I dress for cold rides, when I can be bothered.
It was less about number of jackets and more about layering. Removeable armwarmers under jackets was a big one. Gillets or jerseys under wind jackets (and now the indispensable burner), leg warmers etc. A couple of good but versatile bits of kit will see you through most conditions.
If you want to ride in squall conditions then yeah you're going to be spending a lot of money trying to avoid getting cold and wet.
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If you have something common in the title you can probably filter the activities in veloviewer that way and hence the squares. Probably worth testing ...
Edit: too slow