Planning a return trip to Orkney & Isle of Skye for two weeks either the beginning or end of October, but I’m a nervous about the increased chance of rain. We are planning to take a campervan from Perth to Orkney for 3-4 days then head to Isle of Skye for 3-4 days, if possible we considered trying to fit in Isle of Lewis. We are mainly interested in hiking and the outdoors.
I think the fall colors would be nice my gut tells me to wait until May for better weather. We have been to both in April and experienced periodic heavy rain and wind.
The later you leave it the more travel disruption due to wind is likely.
That is what would concern me more than rain . And I speak from experience of being on Orkney in late October and it raining every day for a week. Incessantly.
You are doing 3 ferry crossings- Orkney to the Mainland, Ullapool to Stornoway and Harris to Skye.
If I was a bookmaker I don't think I could price the odds on at least one crossing not being disrupted - potentially all 3 if Lady Luck was against you. The up side is that the roads and all the historic sites will be quiet, probably very quiet.
There aren't many trees on Orkney, the outer Hebs or Skye, so not really the best places for the fall colours.
It is a very hard call to make, given the pluses and minuses but May feels like a better time for this. I know I should be encouraging off season travel.
You are much more likely to be OK weatherise if you can make it early October rather than late October. Personally I wouldn't try to fit in Lewis & Harris as well as the Orkneys and Skye. In fact it would probably make more sense geographically to miss Orkney and combine Skye with Lewis & Harris. You could drive from Perth to Skye via the bridge, explore Skye, then take the ferry from Uig to Tarbert, Harris, then explore Lewis & Harris before taking the ferry from Stornaway to Ullapool and from there head back south to Perth. Plenty of hiking opportunities in both locations. Lewis & Harris also has some ancient sites, which while not as many as Orkney, are still impressive.