Behind the Scenes on Tradewind’s BOS-NY Shuttle

On Prescott Street along the northwest edge of Boston Logan International stands a smartly landscaped Modernist building clad in sleek gray steel and stained oak. Offering an artful contrast to the massive parking garage and Massport administration building across the way, this is the Signature Flight Support private terminal. It’s where Tradewind Aviation customers board their 50-minute flight down to the Westchester County airport in White Plains, 20 miles north of Midtown Manhattan. From there they take livery service or the Metro-North commuter train into the city.

Passengers arrive 15-30 minutes before departure from Logan and gather in a clubby lounge with leather seating, attractive lamplight, soothing acoustics, and a soaring glass wall that looks out to the airfield. On this mid-winter Wednesday evening, with a Nor’easter rumbling up the Seaboard, the Tradewind 5:25 departure shows a full manifest of eight passengers, each intent on making a pre-storm getaway.

Soon they’ll be aboard a Pilatus PC-12, climbing to 17,000 feet of altitude in a streamlined, Swiss-made turboprop that cruises at 300 miles per hour. Inside the PC-12 it’s cozy but truly comfortable, with pewter-grey leather upholstery on the seats, the walls, and even the headliner. Baggage gets stowed in an open-rear compartment and standard seating configuration is four rows of two seats flanking a center aisle. This aircraft is squeaky clean and still has that new-airplane smell.

Climate control is critical to making air travel work as it should, and this plane is best-in-class in that department—another reason for its popularity with corporations and private aviation companies. Small planes flying scheduled routes in this part of the world are known to buzz along in summertime with an open cockpit window to cool the pilot, even as passengers feel the heat. Not so with the PC-12, which is also notably low-decibel in its cabin, especially for a prop plane.

At the far corner of the lounge, outbound travelers from this and various other flights speak with Signature concierge staff about their needs and arrangements. The Tradewind pilot, Trevor, his co-pilot, Omar, and a ground representative, Craig, converse with the clientele, many of whom they know on a first-name basis. Clearly this is high-touch, white-glove customer service, but it never seems forced or scripted. Instead there’s an easy camaraderie flowing between crew and passengers.

One flyer is running late, and indeed won’t arrive until 10 minutes before scheduled departure. None of the others bristle at the minor delay. “I think it’s a matter of them knowing that next time it could be them,” muses Craig, himself a trained pilot and flight instructor. “And with private aviation, altered departure times can work in the other direction. If everyone’s here and it’s 20 minutes before scheduled takeoff, we pack up and go.”

A luggage dolly is off to the side, gradually taking on the minimal baggage carried by these attorneys, consultants, investment bankers, venture capitalists, corporate finance officers, or the occasional university professor on a speaking engagement. Catering setup is part of the prep, although given how quick the trip is, in-flight food-and-beverage service is casual. “It’s maybe a two-beer flight,” estimates Trevor, who learned his trade as a bush pilot in Alaska. “Unless somebody’s had a particularly trying day, in which case there may be time for three.”

He has already completed his pre-flight inspection of the PC-12’s airframe, checked tire pressure, and examined his gauges for any possible irregularities—now he’s back to his customer-care detail. “We’re the ground crew, the ramp agents, the baggage handlers, and the flight attendants, along with our main job of piloting the aircraft,” explains Trevor. Tradewind policy is always to man the cockpit with two crew members—not a practice found everywhere in private aviation.

You can book this Tradewind flight through a travel agent or directly with the company. The price is $395 each way, but as low as $295 if you’re a regular who purchases books of tickets at a time—and they’re transferable to clients and family members. “These are people whose time is worth $150 an hour or in many cases much more,” says Craig, “so if they get in one more meeting, skip the need for a hotel night, or get the workday accomplished but stay married because they’re home for dinner instead of not, that’s where the value is.”

As he finishes his thought, a regular on the route—a gentleman with salt-and-pepper hair and wire-rimmed glasses—walks over, shakes hands, and starts up a conversation. Very likely their chat could be about his son’s peewee hockey team—Craig knows the boy’s name, his position, and all about that shorthanded goal he scored in last week’s game. It’s a game, incidentally, that the dad returned home in time to see, after a day spent doing business in New York. So, yes, there’s work, there’s life, and there’s traveling strategically to try and keep the two in balance.

Boston is More Than its Institutions—Right?

One of the highest market-cap companies in the world is depicted in “The Social Network” as the product of a young man’s intense desire to upgrade his standing in the world of Boston institutions—by gaining entrance not to Harvard, where he was already enrolled, but to an exclusive Harvard “final club.” True, Harvard lies across the Charles River in Cambridge, but we won’t split hairs—the movie makes a telling point about the importance of affiliations, in this corner of the world.

Somehow, the two adjacent cities, with their combined population of 750,000, have ended up with a cohort of consequential institutions you might expect to find in a place three or four times larger. One result is a professional class for which direct affiliation with the various monoliths, or a couple of degrees of separation, is common reality.

Harvard University

And so you must legitimately own a garment imprinted with MIT, Harvard, Boston University, Massachusetts General Hospital, Tufts University, Boston College, the Kennedy Library, Northeastern University, Brigham & Women’s Hospital, the Museum of Fine Arts, the Christian Science Church, the Boston Pops, and so many more—or else be closely affiliated with someone who does.

What’s sometimes forgotten is that Boston-area achievers who serve those institutions have commercial and professional connection with, um, the rest of the world—and particularly with the Northeast region. Tradewind, as Boston’s go-to private aviation connection with New York City (with both scheduled shuttles and private charter options), pays close attention to the travel trends that Boston’s innovators and thought leaders tend to generate. It may be, of course, that more than residents of other cities, Bostonians value the flight home most highly—it returns them to the narrow streets and ivy walls that represent uniqueness and greatness to them.

“It’s human nature to want to identify yourself with something of consequence—something that’s widely recognizable,” says Robert Savage, professor of Irish history at Boston College and a product of the Boston suburbs. “The Boston area is just so dense with these things; it can be overwhelming if you haven’t learned to navigate it.”

Boston College

Arriving as a Harvard freshman from Southern California 30-odd years ago, John Kelley appreciated the relatively ancient history of Boston and Cambridge because it made his new environs understandable. “When you come from far away, you arrive here with some basic knowledge of the place, given how many old, well-known landmarks there are,” says Kelley, CEO of the sports-performance company CoachUp. “That makes it easier to get acclimated, if you’re not intimidated by it.”

This brings up the issue of how welcoming—or not—Boston can be. New arrivals could stare at vehicles with three or four showoff windshield stickers and a parking decal for some chic neighborhood, plus various other insignia bespeaking insider status, and feel alienated. Mark Twain famously said: “In Boston they ask how much does a man know, and in New York, how much is he worth.” That’s very nice, but in the Information Economy, knowledge and wealth are tending to merge, removing some nobility from the pursuit of higher learning and thus some of the solace a Bostonian might take in Twain’s observation.

John F. Kennedy Presidential Library

Savage wonders if a movie set in any other city would feature an exchange like the one in “Gone Baby Gone,” in which the Boston street kid played by Casey Affleck questions Ed Harris’s character, a police detective, about his last name, Bressant. “It’s the kind of name they give you in Louisiana,” comes the answer, to which Affleck replies, “Oh yeah? I thought you were from here.” Those two words, “from here,” have clearly been a point of contention for the transplanted detective.  “You might think that you're more ‘from here’ than me,” he growls back, “but I've been living here longer than you've been alive. So who's right?”

As longtime director of events at the John F. Kennedy Presidential Library, Amy Macdonald served as a guide to the city for a stream of noted writers, musicians, and thinkers. “There’s a certain type of very famous, very accomplished person who stands in that I.M. Pei-designed building with its amazing Atlantic Ocean view, relives the JFK presidency, and appreciates the high ideals Boston can breed,” says Macdonald. “The U.S. poet laureate, Billy Collins, told me the experience gave him tingles.”

The worldly types she met from New York and Los Angeles were too polite, in her estimation, to dismiss Boston as provincial and parochial, though they commented freely about how early the bars closed and the subways stopped running. “Their attitude,” Macdonald says, “seemed to be: ‘Even though you haven’t got much nightlife you’ve got these famous universities and hospitals, and that seems to make you happy—but I’m going back to my real city.’ ”

General Electric Boston Headquarters Rendering

Photo credit: General Electric, © Gensler

Kelley works in corporate offices down the road from where General Electric is creating, in his words, “their own micro-city” in the revitalized Seaport District. He feels GE’s relocation from Connecticut will do much to answer the question of whether Boston’s old-line institutions will continue to define the town.

“GE seems to have this whole question figured out,” Kelley says. “They’re building their headquarters as a village of knowledge and innovation; it’s not walled off, it won’t have ivy growing on it, so it’s got the feel of a global crossroads.” Sounds from that like the country’s 10th-largest employer will soon be its own institution in Boston—just not the sort of Boston institution people “from here” have long been used to.