October

[KDean]

The earliest I can do it this year is October ? Planning "The Safe Way " over 18 days ...or put it off until early next year ....not sure about weather & maybe ice in Scotland at that time ?

 

[Ajax Bay]

On the plus side, over 18 days you will have plenty of daylight for 50 miles a day, and the midges should have 'gone'. In any 18 day period in October you're bound to get some 'weather'. Ice? Doubt it (and mitigate that risk by going Great Glen and riding in the middle of the day).

 

[Edwardoka]

It's definitely doable - ice certainly won't be an issue that early in the season, but Scotland can have rubbish, cold, wet weather in midsummer, never mind October where the days are much shorter, especially the further north you go.

That's not to say that good weather at that time of the year isn't possible, just that you'll need to be luckier than usual to hit a weather window.
As a rule of thumb, the east coast is generally a lot drier but colder.