The Great Divide is a series about inequality.

As the travel season kicks into full swing this Memorial Day weekend, many of us are anticipating the rites of the modern vacation with a quiver of dread — crawling along the Long Island Expressway; stalling in endless security lines; gnawing on pretzels while squeezed into ever-smaller airplane seats. It’s hard not to envy today’s über-rich, whose getaways, on private jets to Caribbean villas, take place far above the sweaty fray of mortal tourists.

But not long ago, on a journey through India, I began to see things a little differently. For two weeks, I had been fairly battered by the daily chaos of budget travel. Then, on my last night in Kolkata, I met up with some particularly affluent friends who had spent their vacation escorted by private staff from one security-gated refuge to the next, and who were staying in a palatial five-star hotel on the outskirts of the city. In their cocoon of opulence, they quizzed me about my comical but vivid excursions, which had left me both exhausted and exhilarated. I began to realize that they suffered their own form of travel envy. The sense of control money provided them had also served to deaden their experience.

The economic gulf between travelers is part of a great tradition. Since the birth of leisure travel, aristocrats have been devising creative ways to isolate themselves from hoi polloi.

It began with the ancient Romans, whose elite set off every summer along the Appian Way, sipping Falernian wine in sumptuous carriages, to fantastical villas by the Bay of Naples. But even the slightly less well-to-do had to tolerate far less regal conditions.

The first-century philosopher Seneca, who took a room at the resort town of Baiae, was kept awake all night by partying neighbors — classical spring breakers. “Why must I look at drunks staggering along the shore or noisy boating parties?” he railed. Another disgruntled hotel guest in Pompeii scribbled his complaint on the wall: “Innkeeper, I urinated in the bed. Yes, I admit it. Want to know why? You forgot the chamber pot.”

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It’s precisely when Roman travelers ventured out of their comfort zones that their accounts become most compelling. Classical literature contains a litany of complaints about bad food, rock-hard mattresses and pushy guides. The Romans may have had paved roads and plumbing, but meals at highway inns were rumored to include human flesh in the stews, with unlucky travelers discovering knucklebones or worse. Fellow travelers could be oafish: Plutarch hummed to himself to block out the noise of drunken mule drivers. And rapacious locals were everywhere. One Roman traveler in Alexandria griped: “Unus illis deus Nummus est” — “They worship only one god there: cash!”

But the intrepid Roman traveler was able to behold many wonders: festivals and sacred sights, the pyramids of Egypt, the oracle of Delphi, the battlefields of Troy. To quote another piece of ancient graffiti found in a tomb in Egypt’s Valley of the Kings: “Those who have not seen this have seen nothing. Happy those who have!”

The words echo throughout history. When leisure travel was revived in Europe in the 18th century, a well-connected young gent on the Grand Tour could stay in the palaces of royals, dining on roast quail and dancing in all-night masked balls. But the rewards for the impecunious traveler could also be great. The young James Boswell, effectively backpacking across Germany and Switzerland, filled his journal with remarks that would impress any Travelocity reviewer: his inns were “dreary,” “comfortless,” “wretched,” “indifferent,” “grievous” and “sorry.” Supper tended to be “pitiful,” the landlord “a stupid, miserable-looking old man.” But his accounts involve hilarious encounters with eccentric characters and alluring women, and are eagerly read by historians and lovers of literature today.

In the United States, traveling for pleasure largely began after the Civil War, when the burgeoning middle class was able to take rejuvenating summer trips to the Adirondack Mountains in upstate New York, hiking, canoeing and sleeping in rustic tents — and just as often being harassed by insects and soaked by rains.

Despite such democratic origins, America’s rich quickly found their luxury niches, as the Rockefellers, Carnegies and Vanderbilts built their own “Great Camps” in the Adirondacks. Arriving by private trains, the families of robber barons could disport for the entire summer in artistic elegance, surrounded by armies of servants and chefs. (It’s from this seminal period that the word “vacation” entered common usage, replacing the British use of “holiday.”) But to purists, the wealthy were merely playacting at being in the wilderness and recreating their Fifth Avenue drawing rooms in the forests.

THE more popular travel became, the more extreme the lengths the rich would go to set themselves apart. No sooner had the Victorian businessman Thomas Cook created the first package tours to Europe than scions like Lord Randolph Churchill (Winston’s dad) realized they could travel in style to just about anywhere. Churchill set off in 1892 on an exotic African safari, with 200 local porters carrying 20 tons of baggage, which included a dozen crates of Bollinger Champagne and a grand piano. But the deadening effect of all those creature comforts had a price: Lord Randolph’s memoir, “Men, Mines and Animals in South Africa,” is one of the most pompous of the colonial era.

Today the 1 percent are going to even greater lengths. Some use their wealth to positive effect, making charity-driven excursions to remote villages in Madagascar, while others are more self-indulgent, flitting about in light aircraft to shake hands with Amazonian shamans. By early next year, for $200,000 a head, travelers are expected to be able to take a commercial spaceflight on Virgin Galactic, including a whole five minutes of weightlessness.

But perhaps gravity isn’t the only thing missing from these luxury travels. Epictetus, the first-century Stoic philosopher, argued that a certain degree of physical discomfort was an integral part of a rich experience on the road. He used as an example the Olympic Games, where 40,000 travelers crowded into a remote Greek sanctuary, like the Woodstock of antiquity. “Don’t you swelter all day in the sun? Aren’t you jammed in with the crowds?” Epictetus asked. “Don’t the din and the shouting and the petty annoyances drive you mad? But of course you put up with it all because it’s an unforgettable spectacle.”

What we all want from travel is essentially the same, a vivid and memorable experience. So when I’m lined up on the sands of the Jersey Shore this weekend, and I see the first megayacht gliding across the horizon toward St. Barts, I will smile and ask myself: how much fun can that really be?

But I’ll try not to get too self-satisfied. We travelers should all remember that, even with increasingly affordable air travel, tourism is very much a first-world pursuit, and only a small percentage of the world’s population travels for pleasure in any capacity. (Statistics are few, but the United Nations’ World Tourism Organization calculated around the turn of the millennium that only 3.5 percent of people on the planet traveled internationally, a figure that was expected to rise, all going well, to 7 percent by 2020.) So when you think about it, even the chance to spend a few days in a Holiday Inn in Ontario makes you part of a modern aristocracy.

Tony Perrottet is a contributing writer at Smithsonian magazine and the author of “Pagan Holiday: On the Trail of Ancient Roman Tourists” and “The Sinner’s Grand Tour: A Journey Through the Historical Underbelly of Europe.”