I've purchased air fare for me and my husband for a trip to Scotland, in May, (18 days, including those arriving and departing from Edinburgh). I've put together a tentative itinerary but have yet to book any accommodations. However, based on some reading here (and elsewhere) and some queries I've made, now is apparently not too early to begin doing so. --So any input on this and anything below will be appreciated.
First, I'm trying to limit our self-driving to the Isle of Skye, but I'm open to extending this. This is the reason why (and again your thoughts will be appreciated): We made a trip to Ireland a couple of years ago (also in May and a similar length of time). After three days in Dublin, we picked up a car (manual, which I now regret), and my husband drove us counterclockwise around the island, including Belfast, other towns (large and small), along scenic drives, across passes, etc. Though I charted us into some tight driving situations and onto some surprisingly narrow roads--surprising, even though I had read about the roads beforehand--we had no incidents (no damages, no additional fees, nothing, car and ourselves returned intact). I thought my husband drove great (better than here in the States), but ... in discussing our trip with friends afterward, I realized the stress of anticipating each day's driving had diminished his, overall, enjoyment of the trip.
He says he's willing to give the driving "a go" again, but I'm wondering if the itinerary below--traveling primarily by train--will work just as well or almost as well as hiring a car and driving ourselves. (For the record, my husband is not a timid man or a timid driver, but ... as he definitely felt under some unexpected pressure driving in Ireland, I'm conflicted about how I should plan this trip.) I will definitely reserve an automatic and add myself as a second driver (something I did not do before--again regrettably--to save money).
2 Nights in Edinburgh > Train to Glasgow
3 Nights in Glasgow (with a train to Stirling and back to tour the castle and an all-day Rabbies tour to visit castles and villages in and around Stirling and Fife) > take the West Highlands Train to Fort William
2 Nights in Fort William (with bus, Uber, or taxi to visit Glen Coe) > Train to Mallaig > Ferry to Armadale to pick up a car for Skye
3 Nights in Portree > and then Skye Bridge and over to Eilean Donan Castle before returning to Kyle of Lochalsh to drop off the car and pick up a train to Inverness
2 Nights in Inverness (with an all-day Rabbies tour to Clava Cairns, Cullodin, Glen Affric, Loch Affric, Beauly Priory, and Loch Ness but not Urquhart Castle)
1 Night Ullapool (on Rabbies North Coast 500 Tour)
1 Night Thurso (on Rabbies North Coast 500 Tour)
1 Night In Inverness (end of Rabbies North Coast 500 Tour) > Train the next day to Edinburgh
1 Night in Edinburgh before our next day's departure for home
Thus far, it appears that hiring a car on the Isle of Skye for our use there will be easy (if booked in advance, of course), but I haven't yet found evidence that it is routine or easy to hire a car on Skye and drop it off in Inverness or in Edinburgh--alternatives, which would negate our need to travel by train to Inverness and book a tour there to see the nearby sites mentioned above, as well as--potentially--some others.
The Rabbies North Coast 500 Tour, which I want to do regardless, has to be situated where it is in the itinerary because those tours will be leaving Inverness on Thursdays in 2020. (I did email to confirm that, and I'm keen to leave the driving to someone else for this portion of the trip.)
Sites that I have, so far, not been able to include in the itinerary above that I had on my list when I began planning this trip are ... Urquhart Castle, the Leault Working Sheep Dogs, the Scottish Crannog Centre, and a short trip to Pitlochry.