Isle of Skye/Fort William best time of year for hiking

Statistically speaking, late May is the Goldilocks balance of temperature, precipitation and daylight hours--not too cold, not too warm and not to wet and close to longest daylight month:

Northern Scotland Met Statistics

Sunrise-sunset

That said, expect to get wet even in the month of May (or any other month of the year).

We plan to hike the Highlands in 2017. I asked the tour company, based in Scotland by the way, which months would be best - choosing between April and September. (I was told to avoid the midges...don't hike in the summer. ) You'll get rain any time, any month. We probably will hike mid-late September and plan for rain and wind, but no/few bugs...

I can attest to encountering no midges the two times I've traveled in the highlands in May. Lovely blue bells were carpeting some of the meadows. Agreed you want to be prepared for rain. I pretty much lived in my knee-high boots with trousers tucked in, warm sweater, and raincoat & rain hat. Oh, and fingerless gloves.

we did early October 2014, no bugs during that time, we spent 4 days in Ft. William, 4 on Skye. It ws extremely beautiful but we did notice the day light hours are short, but the ruggedness of the hiking gave us all we wanted and our legs wore out before the sun went down! No crowd issues anywhere, only similar hikers wandering around so traffic too is light. We had to leave Skye a day early because a hurricane down in the Caribbean (figure that one out) a few days earlier blew up the Atlantic and forced us to leave the isle earlier than planned due to high winds closing the bridge. Makes you wonder if Hurricane Matthew will have an affect on Scotland in a few days, might take tht into consideration? There were limited numbers of blooming flowers etc but the fall hues were outstanding. Absolute must to have waterproof hiking boots, that grip the rocky trails. Ditto on the rain gear. I am totally pulled back to Skye daily! Here is a link for a great resource for hiking the highlands, the isle and most all of scotland. Hope it helps. http://www.walkhighlands.co.uk/#walks

Advantage of a late spring (May) walking holiday vs. early spring (October) is 16 hours of day light vs 10 hours where day light is the theoretical daylight of sunrise to sunset. (Mid-day in a UK storm can feel live evening twilight with rain). If you push day light hours carrying head lamps is a good idea. We have finished ski tours by moonlight and head lamp illumination when we mistimed tour duration.

An English friend did the Offa's Dyke walk during the fall season. He said that he was often if a dispute with his B&B host as to getting an early breakfast so that he could maximize day light hours.

Regardless of time of year, expect rain and have everything water-proofed or at least very water-resistant. You will need to protect maps (i.e. waterproof map case and/or waterproof/resistant map stock) and guide books. I carry copies of walking route instructions printed on sheets that I can encase in my waterproof map case.

Waterproof rain pants and gaiters help, but walk carrying spare wool or synthetic socks.

My late May experience was midge free.

Don't leave it too late as if a heat wave were to make it north of the border the nasty blood thirsties might be tempted to see who was around.