The Cuillin are not large mountains by world standards, topping out at 992 metres on Sgùrr Alasdair, but they are exceptionally difficult ones. The black gabbro rock weathered to a sharp edge, the ridges narrow to inches, the weather turns instantly. Sgùrr Dearg above Glenbrittle is crowned by the Inaccessible Pinnacle, a vertical fin of rock that requires actual rock climbing to ascend, the only Munro that does so. The Cuillin attracted a particular kind of Victorian and Edwardian climber and have a particular kind of literature about them. Their dark profile defines Skye's southwestern view. On the other side of the island's history, the rugged ground and the poverty it generated drove the Highland Clearances of the 19th century. Landowning chiefs replaced subsistence tenants with sheep, and emigration ships left for Canada and Australia. The population today is less than half of what it was in 1841. Many Skye townships exist now only as walled outlines in the heather.

The Trotternish peninsula, the long finger of land running north from Portree, was warped 10,000 years ago when the retreating ice age glacier stopped supporting the mountainside. Twenty miles of cliff collapsed eastward in what geologists still consider the largest landslip in Britain. What remains is a contorted, unearthly terrain of grass-topped pinnacles, sheer escarpments and disordered green hills. The Old Man of Storr is a 50-metre rock spike standing alone below the main cliff line; you can see him from the road, though clouds often have him to themselves. The Quiraing further north is a more elaborate version of the same phenomenon, hidden plateaus and rock pillars that require a hike to appreciate. Kilt Rock on the east coast is a dolerite sea cliff said to resemble pleated tartan, though the resemblance is generous. The Trotternish road is single-track in places with passing places.

After Culloden in April 1746, the Stuart claimant Charles Edward Stuart spent five months on the run in the Highlands. In June he reached South Uist, where local sympathisers told him he had to get off the islands or die there. Flora Macdonald, a 24-year-old who was not herself a Jacobite, agreed to help. She arranged a passport allowing her to travel to Skye with her Irish maid, Betty Burke, who was the Prince in a dress. They landed near Kingsburgh on Skye on 29 June 1746. The Prince was famously bad at the disguise, taller than most women and inclined to swear in unmaidenly fashion. He stayed briefly in Portree, crossed to Raasay overnight, came back, then made his way south to Elgol and a boat to the mainland. The thirty-thousand-pound reward on his head was never claimed. He escaped to France in September. Flora was eventually arrested and held in the Tower of London; the Prince never wrote her so much as a letter again. The Skye Boat Song, written more than a century later, romanticised the whole affair and bolted the Prince permanently to Skye in popular memory.

There is no airport. The Skye Bridge from Kyle of Lochalsh on the mainland is the main road approach; the A87 crosses it toll-free since 2004. Scottish Citylink coaches run from Glasgow (about 7 hours) and Inverness (about 3.5 hours) twice a day to Portree. Calmac ferries from Mallaig dock at Armadale near the south tip in 45 minutes. The tiny Glenelg ferry, the last manually operated turntable ferry, runs from April to mid-October, taking six cars per trip. Uig at the north end has ferries onward to Harris and North Uist in the Outer Hebrides. Once on Skye, the A87 is a proper road; most of the rest are single-track with passing places. Visiting in July or August without booked accommodation is a bad idea; the police have, in some years, turned travellers back on the A87 approach if they could not name where they were staying.