Done it many a time, but not wild. You will need to make sure he is really secure in his crate and make sure zips close at the top, to stop any snozzle unzipping
I'm sure you're aware that if he worries sheep he could be shot
I would invest in a groomers dry towel, to remove any excess water off him, should it rain, (which it will on Skye) won't be pleasant for him to go to bed in his crate wet. We always had our dog in the tent with us, I felt it safer for her that way. A long line might be useful, unless you're dog has impeccable recall?
Having lived on the Isle of Skye, i can guarantee these two pieces of equipment are a must, an Otom tick remover and a bottle or three of Avon skin so soft (for the midges, well you spray it on you and the midges don't like it)
We gave up tenting a few years back now, we now have a caravan and Charlie loves it!
Happy to help with any advise on things to see on skye
Enjoy
Link for the towel, we find them a godsend in the caravan and at home!
Groomers Aquasorb Towel - Medium
https://www.amazon.co.uk/dp/B003BOCFQ4/ref=cm_sw_r_cp_tai_f-1izbX8ECQ9R