What I See Flying Over the World’s Cities

Airplanes or cities? As a pilot who flies the Boeing 787 Dreamliner from London to many of the world’s largest and best-known metropolises, it’s hard to say which I love more.

Indeed, these passions are as inseparable to me today as they were throughout my childhood in my small hometown of Pittsfield, Massachusetts. As a kid, I often couldn’t decide between finishing the assembly of my latest model airplane—the Boeing 747s were always my favorites—and slowly turning the illuminated globe on my dresser as I read aloud the marvelous names of the cities marked on it.

My new book, Imagine a City: A Pilot’s Journey Across the Urban World, is both a memoir and a pilot’s love letter to our planet’s great metropolises —what they once meant to me as a globe-spinning child, and what they mean to me now as an aviator who sees so many of them so frequently, first from the skies above and then from the ground. I hope that as travelers return this summer, a pilot’s perspective may help us all to remember how amazing cities are—how majestic they appear from your window seat, how decisively they’ve shaped our history and our civilization, and how fascinating they are to explore.

When pilots speak of cities, we often rely on the three-letter codes familiar to frequent fliers. For example, I might text a pilot friend: I’m back from YYZ on Monday at 10am, how about coffee at LHR before your PKX? While, when we enter our destination in the aircraft’s navigation computers, we turn to a separate set of four-letter codes, by which the same three airports—Toronto, Heathrow, and Beijing Daxing Airport—are known as CYYZ, EGLL, and ZBAD.

Our fluent urban shorthand reminds me that airliners would hardly make sense in a world without cities and their need for connection; and that pilots today experience the urban world in a way that no one else ever has before. I’ve flown from London to cities such as Beijing, Istanbul and Lisbon more than a dozen times each; Vancouver, Cape Town, Tokyo, and Boston more than two dozen times; and New York, San Francisco and Los Angeles at least fifty times.

One result of experiencing cities in this manner is that in the days leading up to a flight—to Santiago, say—I might find myself looking forward to a hike and the view from a particular hill, followed by a few hours at the nearby café that serves the best breakfast burritos. Then I’ll remember: the hill I’m thinking of is, in fact, in Lisbon. And those burritos? They’re in Phoenix.

One older colleague I knew used to carry a diary with him wherever he flew, so that after he retired, he could recall with ease his long years crossing the world. Today, alongside my logbook’s legally mandated fields such as the aircraft registration and the departure and arrival times of each flight, I record hasty notes on some of the world’s greatest cities. MEX: Bookstore café south of main road from hotel was closed, try next time. NRT: Sachiko recommends day trip to Kamakura. HEL: Old Olympic pool—chilly but awesome.

The more cities I see, the more I’m struck by how easily we speak of cities in the most basic human terms, that is, as possessing lungs, arteries, hearts, characters and even siblings. I’m also drawn to the idea that each city is formed from smaller entities that may only rarely, if ever, consider the part they play in its wholeness—a biologist might be reminded of the cells of a body, while a pilot who sees so many cities from above, at night, may think of the millions of lights that appear to constitute a single, strikingly beautiful life.

Indeed, to pilots, it’s exquisitely clear that cities are sited or sculpted by nature long before they are by people. Often, an aerial route runs almost parallel to that of a great river. In Europe, this occurs most often on flights between London and Bucharest, when we might first spot the Danube as we pass north of Munich, before following its path through the hearts of Vienna, Bratislava, and Budapest, where we say farewell as it turns sharply away to the south—though we know we’ll meet it again as we near our destination.

On flights from London to Jeddah, we follow the Nile from its Mediterranean delta south through Cairo and Luxor, and on overnight flights the life-giving river appears to be made of light, so closely do human settlements follow its path through the harsh Egyptian desert. Meanwhile, en route to glittering Gulf cities such as Doha and Dubai, we may see both the Tigris and the Euphrates—a reminder that “Mesopotamia” means “the land between the rivers” in Ancient Greek—as we look down on the home of some of our planet’s earliest urban civilizations.

Sometimes a friend will ask me: What’s your favorite city in the whole world? For me, it depends on the season (Cape Town is always amazing, but its climate and beauty are especially striking when you journey there during the Northern Hemisphere’s winter) and on whose path I might cross (San Francisco, for example, is even better when you can make dinner plans with friends who live there). My long love affair with Japan began in high school when I lived there a summer with a host family. Today, whenever I fly to Tokyo, I’m astonished all over again by the largest city that has ever existed.

If it’s hard to pick a favorite city at ground level, it’s even harder to say which is the most striking from the air. A nocturnal approach over London is always special to me, and not only because Heathrow is my home base. If the winds dictate that we approach from the east, our final approach path roughly parallels the dark ribbon of the Thames as it curves through the glowing capital, past the towers of Canary Wharf, the ghostly gray dome of St. Paul’s Cathedral and—so familiar from movies and postcards that it’s hard to believe that what’s about to pass below the wing is the real McCoy—the Palace of Westminster.

Los Angeles, however, might well be the world’s most astonishing place to land after dark. In 1946, Eleanor Roosevelt wrote that “the most impressive time to fly in to Los Angeles is at night, when all the lights are on and the city lies below you like a multi-colored heap of jewels.” The best part of a century later, whenever I descend over the dense and glittering circuitry that lies between the curtain of mountains and the matt and dark waters of the open Pacific, I know exactly what she means.

And then there’s Pittsfield, in western Massachusetts. I see my hometown most often from cruising altitude, on flights between London and Dallas, New Orleans or Mexico City. With around 40,000 people, no one would mistake Pittsfield’s nightscape for that of Boston or New York. After two decades of flying, however, I know precisely which set of lights to look for within western New England’s dark carpet of forest.

In middle age, whenever I recognize the glow where my first journeys began, I feel more and more that I’m looking down on my past, as if the neuron-like patterns of Pittsfield’s lights are a blueprint of my own memory.

And almost always at such a moment—for no cockpit view lasts long when you’re traveling at 85 percent of the speed of sound—I think of my parents. They’ve been gone for years, but whenever I cross Pittsfield’s skies it’s easy to recall our ordinary, long-ago evenings: a steaming casserole is taken out of the oven and laid to cool on the stovetop; I’m sitting at the small wooden desk by the east-facing window of my bedroom, in the light of my illuminated globe and the shadows of my model airplanes, when I hear Dad call my brother and me down for dinner; Mom turns on the light above the kitchen table, and the nightly news, too, and a few more watts are added to the upwards-shining face of home.