I was first there in May 2006
with Jane, and then the next time was November 2009
, with my mum.
And then... January 2012
(this post and the next one), and January 2013
(this post and the next two).
I recommend getting to Skye by taking the route up from Glasgow and then the ferry from Mallaig. The Marine Hotel in Mallaig is decent, or at least it was in 2006. Obviously, I'm a big fan of the Bosville in Portree, though in May it will be pricey. If you're in Portree on Friday or Saturday, you *must* eat in the hotel's Chandlery restaurant; the meal I had there in 2006 was one of the best of my life.
There are various walks near Portree, including the Old Man of Storr, though I've always stuck with the tame ones within a mile of the town because it's been winter and the Old Man of Storr route sounded scary for a lone walker in damp conditions. The circular bus route around the north is wonderful, but you'll be doing at least part of that to get to Uig, anyway. My experience of Skye has been that of someone dependent on public transport (and on a winter schedule at that), and this makes ones options very limited indeed (which is actually part of the appeal). After a day there with a car, you'll be able to tell me
what there is to do on Skye.
To leave, I'd recommend taking the bridge to Kyle of Lochalsh and then doing the route to Inverness. Of course, you could do the whole route the other way around, but that would be anti-clockwise and that's fundamentally wrong.
I really envy you the trip! Of course, it also feels fundamentally wrong to me that you'll be on Skye in May and not in January as God (and off-season hotel bargains) intended. But if you want to see St. Kilda I guess you have to resign yourself to visiting at a time of year that means you don't get to experience Skye with the full quantity of driving rain.