Should we be deterred by the weather in September? We want to travel around the country including Orkney and the Isle of Skye. We will book accommodations ahead of time for Edinburgh and Glasgow and then rent a car for the rest of the trip. Should we book accommodations ahead of time or should we be able to find accommodations once we are there?
Weather is weather, which means it’s always up in the air. September should be a nice month for the most part, but you should always be prepared for rain and wind and clouds and so on.
With Scotland, it definitely pays to make your accommodations ahead of time, especially on the islands, and especially on Skye. You can find a lot of posts here about accommodations either by doing a search, or just going to the Scotland forum and scrolling down and looking at some of the threads.
Yes, you'll need to plan ahead at least for lodging in Orkney as well as your transportation there. Are you considering a ferry or going via Loganair? How many nights for Orkney? I visited in August and thought Orkney was just amazing!
Here is a link to my Trip Report in case you want to know what I enjoyed on Orkney and get an idea of how my clothing worked the last half of August. Waterproof rain gear including rain pants are a necessity for Orkney.
I, personally, am a planner and would not go without lodging reservations but I understand others travel differently.
The days of turning up and finding B&Bs with vacancies are long gone I'm afraid. The Highlands and Islands have very limited accommodation and it gets booked up. You'll need to book in advance. I saw your other post about camper vans. You'll also need to book a place on camp sites.