Which way round?

The record attempts are anti clockwise. If you include Ireland then you can look at the Britrish Isles as being roughly triangular with the base at the bottom. Given that the prevailing winds are basically from the West you are likely to have fewer headwinds anti clockwise around.

Thats the conventional wisdom. However, if you are cruising you want to get to Scotland by mid May to early June to get the best of the weather and the least of the midges. If you are setting off from the South East there is a good chance of a longish period of easterlies/northerlies in early May which can get you to Lands End without beating. If you see that sort of system coming up make the most of it and go clockwise. If there is no sign of that sort of weather, and you cannot wait for it, anticlockwise is probably preferable, particularly if you are going to use the canals.
 
If you are going through Pentland Firth it's easier going east, which means clockwise. That might mean that the tides on the south coast are less favourable, but they are soft southern pussycat tides compared to the evils at the top of the UK. I went clockwise.
 
There is a good rationale for waiting till you get to the harbour mouth then going whichever way the wind is blowing. If you are on the South coast and there is an Easterly blowing when you start there's a good chance it will persist long enough to get you to Land's End so you've eliminated the chances of a beat for at least part of the Channel right away.
 
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