Why It’s Harrowing: Tucked into a tightly cropped valley and surrounded by 16,000-foot-high serrated Himalayan peaks, this is arguably the world’s most forbidding airport to fly into. It requires specially trained pilots to maneuver into this stomach-dropping aerie by employing visual flying rules and then approaching and landing through a narrow channel of vertiginous tree-covered hillsides.

Why It’s Harrowing: The length of the runway—just 7,152 feet—is perfectly fine for small or medium-size jets, but as the second-busiest airport in the Eastern Caribbean, it regularly welcomes so-called heavies—long-haul wide-body jetliners like Boeing 747’s and Airbus A340’s—from Europe, which fly in improbably low over Maho Beach and skim just over the perimeter fence.

Why It’s Harrowing: Because of the diminutive 1,312-foot-long runway perched at the edge of a couloir at 7,550 feet, becoming airborne at the end of the tarmac is virtually impossible. Instead, you drop down the face of a 2,000-foot cliff until you start flying. Says bush pilot Tom Claytor, "The rule in the mountains is that it is better to take off downwind and downhill than into wind and uphill, because in Lesotho, the hills will usually out-climb you. It's a little bit hard to do the first time."

Why It’s Harrowing: Wedged in by mountains and the Atlantic, Madeira Airport requires a clockwise approach for which pilots are specially trained. Despite a unique elevated extension that was completed back in 2000 and now expands the runway length to what should be a comfortable 9,000 feet, the approach to Runway 05 remains a hair-raising affair that pilots absolutely dread. They must first point their aircraft at the mountains and, at the last minute, bank right to align with the fast-approaching runway.

Why It’s Harrowing: Perched on a precipitous gale-battered peninsula on the island’s northeastern corner, the airport requires pilots to tackle blustery trade winds, occasional spindrift, and their own uneasy constitutions as they maneuver in for a perfect landing (there’s no margin for error) on a runway that’s just 1,300 feet long. "Shorting this means ending up in the cliffs," says one pilot matter-of-factly, "while overshooting it means an uncomfortable go-around. Either way, you’ll want to bring the Dramamine."