How to make your dream of becoming a travel writer a reality

Young, poor and traveling: Mark Chesnut wasn’t a travel writer yet when this photo was taken in the 1990s, but he knew what he wanted.

If you ask fifty people to name their idea of a dream job, at least one of them will probably say “travel writer.” I’m one of those people. Who wouldn’t want to get paid to travel around the world and enjoy free stays in luxurious hotels, international delicacies, and visits to world-famous tourist sites?

Actually, most people wouldn’t want the job when it comes right down to it, because most people wouldn’t want to earn legendarily low writer’s wages, even as they enjoy the magnificently glamorous perks. (I supplement my travel writing with copywriting, branded content, and consulting for travel industry clients. But that’s another story.)

I created this 10-point plan for those who do suffer from a wanderlust more powerful than their common sense. It’s those daydreamers who sometimes ask me how I got into this career.

The truth is, I don’t really know the best path to become a travel writer. I never followed some strategic, predetermined route to get to where I am now. I just followed my passion. After graduating from college, it took me about eight years to gradually steer my career toward the prestigious halls of the nation’s leading travel trade publisher. Once I was there, things started to fall into place (even after I was laid off).

So, for those of you who long for a life on the road, here are the steps that I took. You can ignore any details that don’t apply to you.

1. Study whatever you want in college. Get drunk too. Maybe get a trendy haircut and wear eye shadow on your lips.

Oh sure, a fancy degree in journalism or creative writing would be a great idea if you want to be a travel writer. But you don’t really need specialized education to be a writer. You just need to write well, get your point across, and understand the industry. I had no specific goals when I enrolled at the State University of New York at Albany—aside from spinning tunes as the DJ of Club 91, a weekly dance music show on the university’s radio station, where the synthesizer-driven beats got me pumped up for drunken nights out at Albany’s hottest New Wave clubs. I did my best to look the part, with thrift store clothing, heaps of black eyeliner, and naturally red hair that I sometimes enhanced with various shades of blond, either combed down to cover one eye or sprayed up with so much cheap hairspray that even a hurricane couldn’t have moved it. I also found that green eye shadow made an especially stylish fashion statement when applied to the lips. My makeup even stayed on when I got so drunk that I fell asleep in a snowbank outside of a dance club called 288. Luckily, my friends found me, woke me up, and escorted me home.

What does all of this have to do with my formation as a travel writer? Nothing. But it’s all I can tell you about my college years. I guess I should mention that I did work in the library throughout my time in Albany too, although that doesn’t have anything to do with my eventual career, either. I even studied a bit and got decent grades (the State University of New York is an admirable institution, by the way, and supposedly the largest network of universities and colleges in the United States; my mother and sister both got degrees from SUNY Brockport and my father taught there, so you could say we’re a SUNY family). But my area of study wasn’t related to what I do now: I had a major in Communications with French and Spanish minors (read that out loud and it sounds like I was learning how to converse with coal mine workers in France and Spain).

Mark’s New Wave haircut was a key part of his university education strategy. His grandfather never quite understood.

2. Move to where the work is, even if it’s only because your mother doesn’t want you to come out to your grandfather.

Since being a travel writer involves travel, you’d think that it wouldn’t really matter where you live. But it actually does. There are two reasons for this: 1) If you want a permanent, full-time job with one company, you may need to be where that employer is located (unless they allow telecommuting). 2) If you’re freelancing and plan to take press trips, you need to be somewhere that’s fairly well connected by air to far-off destinations.

I didn’t have travel writing in mind when I was in college, so I wasn’t thinking about any of this when graduation approached. But I did want to live in a big city since I wanted something different from my small-town upbringing. My options were limited since I had no jobs lined up and no real money saved as graduation quickly approached. I realized that I needed a place to live for free until I could find a viable source of income. Maybe moving back home to Brockport would make sense, if only for a while.

Or maybe not, as I discovered during one definitive phone call with my mother. As usual, I still tried to keep lines of communication open to talking about the fact that I was gay, and I thought that eventually, more people in our family should know. After all, being gay isn’t a bad thing, right?

“I know it may be weird to talk about my sexual orientation with Pop and Rarene,” I told my mother, referring to my grandfather and aunt, both of whom lived with her. “I just want you to know that you can decide when you think is the best time to let them know that I’m gay. I’ll follow your lead.”

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“If you were going to live here with us after you graduate, then we would deal with that,” she answered calmly. “But since I know the last thing on earth you want is to move home, then there’s no reason for them to know.” Case closed. She hadn’t even asked me if I wanted to move back, or if I wanted to come out to the rest of the family. I didn’t know how to respond, so I changed the subject to some boring topic like how many Buffalo wings I’d eaten that weekend.

Half of her statement was on target, I have to admit. I really didn’t want to move back in with my family. I was considering it only because I was broke and had no post-graduation job. At any rate, my mother helped to obliterate any doubts I might have had. It was a bit harsh, but what could I do? I’d already sent her books and magazine articles about how parents can deal with having a gay kid, and her response was always radio silence.

Her attitude, to be honest, pushed me to be independent and do what was best for my own mental health: to go out into the world on my own. The end result was positive.

Still, I needed psychological support. A university therapist helped me to confront the three overarching issues that vexed me during my senior year: my graduation and career anxiety, my mother’s unwillingness to talk about homosexuality, and the breakup of a disastrous relationship with my first-ever boyfriend (we’ll have to deal with that in another essay; it would be too distracting now to bring up the beautiful boy I dated who unintentionally looked like a young Lana Turner. See? You’re already distracted and trying to picture what he looked like. Unless you don’t know who Lana Turner is, which is quite likely).

In spite of my mother’s reticence about fully accepting my sexual orientation, she still managed to be warm in other ways during my final year of college. She even bought me my first (and so far, only) car as an early graduation gift: a spiffy little-used sports car, in the same maroon color as my grandfather’s long-gone luxury sedan. I called my car the DiscoLiner to reflect my love of dance music.

As it turned out, I didn’t have to look too hard to find a post-graduation crash pad. My salvation came from one of my best high school friends, who was confusingly named Mark too (he was the same guy who as a teenager had coveted the name-brand cookies and other name-brand snack food that my mother used to buy me). Mark had moved to New York City several months before my graduation, and he offered to let me sleep in his living room in Brooklyn, rent-free until I found work.

3. Find a job that’s somewhat related to what you really want to do—preferably, one that allows you to commit aviation fraud.

Few people land their dream job right away. Like many recent graduates, I made frequent job changes in my early years. Only a couple had travel benefits, but first I had to suffer through an excruciating job as an “executive assistant” to a high-ranking director at a major cosmetics company, which sounds glamorous but mostly involved arranging magazines and a water pitcher just so before he arrived every morning to his corner office, then fetching his dry cleaning and occasionally chatting by phone with a mildly famous celebrity who’d lent her name to a line of fragrances. It was all a bit like The Devil Wears Prada, but less interesting. (I also accidentally ate dog poop on a croissant while I worked there, but that’s one more story that must wait for another time.)

Much better was my job as an editor at a small medical publisher, which provided the unexpected opportunity to fly free by committing aviation fraud. It was an idea hatched and proposed by the company’s president. After noticing the airline memorabilia that decorated my cubicle, he realized that I was a travel addict and decided that I could help him maintain his elite frequent flyer status with a now-defunct airline that was one of the world’s most legendary carriers at the time. He asked me if I’d like to fly an annual mileage run to California so that he could keep his elite status.

To do this, I had to assume his identity, which was much easier than you might think. Back in the late 1980s and early 1990s, believe it or not, airlines didn’t yet ask passengers for identification at the airport. I could just march my 24-year-old butt up to the ticket counter at JFK, glide through security, and strut effortlessly aboard a glistening, Los Angeles-bound jumbo jet, all using the name of a 50-something businessman. It was disorienting at first to hear the staff address me by someone else’s name, but I got used to it quickly. I’d do just about anything to fly for free.

4. Build your personal route map.

We all have route maps, even if most people never document them. A route map is a diagram of everywhere you’ve been— whether by plane, car or even by foot. We’ve all traveled somewhere, even if it’s just to the neighboring town to buy porn as a teenager (okay, maybe that was just me). Whatever the map looks like, where you’ve been says something about who you are.

I got hooked on travel so young that I started drawing my own personal route map in middle school, and I updated it every time I flew a new route. The point is, if you’re interested in becoming a professional travel writer, it’s not a bad idea to follow your passion now and start exploring the world, even if it’s on your own and even if you’re not traveling far from home.

Mark Chesnut’s personal route map, circa 9th grade. He’s such a travel nerd he’s saved this map for decades.

You don’t need to be rich to travel. I didn’t have much time or money to travel when I was in my twenties, but I squeezed maximum value out of every opportunity. And even though I wasn’t writing articles for any magazines yet, I took notes, wrote journals, and snapped photos to document every important moment. It was instinctual. I didn’t want to forget a thing about any journey I took.

I taught myself how to work the system. A key part of this involved learning the fine art of being bumped from a flight.

During trips back to see my family, I aimed to be the first person to volunteer my seat and get bumped when flights were oversold. Depending on the airline, that got me either a free domestic round-trip or a cash voucher. I used those credits to visit San Francisco, New Orleans, Los Angeles, and San Diego.

Frequent flyer miles are another important tool for anyone obsessed with travel. I hoarded miles and scoped out irresistible deals. One of my biggest coups was using a triple-mile promotion on a $250 round-trip ticket from Newark to London Gatwick, which produced enough frequent flyer mileage for a free ticket to Buenos Aires. Between 1987 and 1991 (all while I was in my early twenties), I added England, Holland, Argentina, the Dominican Republic, Puerto Rico, and Mexico to my international route map. Not bad for a kid just out of school whose salary had only risen from $12,000 to $25,000 a year.

5. Get media attention—even if you’re not really newsworthy.

An easy way to dip your toes into travel journalism is to inject yourself into the news. One thing to note: It’s not easy to get a TV reporter to notice you when you’re one of hundreds standing outside of an airport terminal. Back in 1989, I had to stare at one of television journalism’s biggest rising stars for about ten minutes before she even looked at me. I was just a face in the crowd, standing in a seemingly endless line outside of New York’s LaGuardia airport on a chilly day in 1989. Hundreds of people had gathered, eager to pay the ridiculously low fare of $12 to board a shuttle flight to Boston or Washington, D.C.

The cheap tickets—and the national news coverage—were all because this particular airline was desperately trying to attract passengers back during a crippling strike. The flash sale even included bonus frequent flyer mileage.

I knew it was wrong to cross the unions’ picket line. But the trip. The mileage. I was young and poor and desperate to travel. So I donned my psychological and moral blinders and walked straight into that overcrowded terminal with a crisp $20 bill in hand. And when I saw that up-and-coming reporter, I wanted her to document my transgression.

I could have hidden from the cameras. But no, this was my big chance to be on the national news. Years earlier, a TV reporter interviewed me in front of Greater Buffalo International Airport after J.J., Kenny, and I had slept all night on the outside sidewalk in order to get a twenty-nine-cent promotional fare on New York Air (yes, twenty-nine cents, and yes, our parents were permissive enough to let their teenage sons fly all the way to New York City and stay unchaperoned in a hotel).

An interview on a national newscast would take me to the next level. Eventually, the famed reporter did approach me for a one-line sound bite, which I completely flubbed because her sophisticated, international speech patterns made me so self-conscious of my Great Lakes accent that I tried to answer her with the same high-class vocal intonation. Instead, I sounded like an extraterrestrial who’d just learned English. She disappeared before I had time to do a makeover, leaving me to hop aboard a shiny jet on my next adventure.

If you don’t find yourself in front of a camera talking like an idiot with a fake accent, it’s probably best to just follow a more professional path, as highlighted in the next step.

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6. Use freelance work and personal projects to steer your full-time career in new directions.

I didn’t know exactly where I should be working, but I knew what I liked: being creative, writing, and traveling. So I decided to follow my passions and see where they led.

I enjoyed my work, but I knew there was something better out there. I began using freelance endeavors and personal projects to steer myself toward a more rewarding future.

To prove my ability as a travel writer, I took on small freelance assignments that would result in writing clips that I could then show to other publishers. I began by writing a monthly travel column—with no pay—for a tiny monthly newspaper that was distributed for free in Greenwich Village. Then I founded a fanzine (there were no websites or blogs back then) called Skyjack Magazine, which was dedicated to “gay people who fly.” For Skyjack, I wrote and published off-the-wall articles and interviews with flight attendants, pilots, and snarky LGBTQ travelers who reveled in the campy aspects of the airline industry (one of Skyjack’s ongoing columns was “More Movies the Airlines Won’t Show You,” which provided tongue-in-cheek reviews of bad airline disaster movies and other films that celebrated over-the-top images of air travel). Believe it or not, I actually made money on Skyjack, attracting paying subscribers and even an investor who bought the publication and then paid me to stay on as the part-time editor for several years.

Mark Chesnut’s book, Prepare for Departure, is a quirky memoir about a single mother, a misfit son, inevitable mortality, and the enduring allure of frequent flyer miles.

7. Don’t ever give up.

You’ve got to keep on going. That’s good advice for any career or goal.

If I’d given up, I wouldn’t have become a travel writer. For months, I scanned the want ads and applied for any full-time job I could find in travel publishing. One particular employer kept popping up in the listings. The company, which owned a variety of top travel industry publications, sounded like the perfect place for me. The only downside: the office was in suburban New Jersey, which required a bus ride from my home in Manhattan. But passion outweighs practicality, so I applied for an editorial job there and got an interview.

They didn’t hire me.

A few weeks later, I applied again for another job, in a different division of the same company. I got an interview. They didn’t hire me.

I tried a third time with yet another division. Still no offer. And yet those “help wanted” ads from the Garden State kept appearing, enticing me.

I decided to give it one last shot. The human resources guy seemed to like me enough to keep showing my résumé around the company, so it would be silly not to keep trying. Luckily for me, the fourth time was the charm. After just one interview with the department head, the company hired me as an assistant editor in the custom publishing department. I have a wonderful woman named Jane to thank for giving me my first shot on that career path.

Custom publishing is different from journalism. It’s an editorial hybrid that goes by many names—branded content, sponsored content, or strategic content, for example. But they all pretty much mean the same thing: advertorial content, created in cahoots with a sponsor who pays big bucks for promotional material that’s good enough to attract attention and engage readers. I was finally writing about the travel industry. It was spectacular. During my time in that position, I wrote and edited copy for clients ranging from tourism offices to hotel chains and airlines. After just a couple of months, my boss sent me on my first press trip. I was in heaven.

That work prepared me for another position, within the same company, that involved travel on a regular basis— thanks to another wonderful manager, Claudette, who hired me to become her Caribbean editor. Throughout those years, I never stopped freelance writing, either; I even found time to write an entire book called The Gay Vacation Guide: The Best Trips and How to Plan Them.

8. Learn how to fake it.

You may think travel writing is all glamour, but if you’re a serious travel writer and editor (especially if you work for travel industry publications rather than consumer outlets), you must also be able to comprehend complex industry issues, and

sometimes pretend you’re interested in less-than-fascinating topics. Trade publications are produced for people who work in the industry—travel agents, tour operators, hoteliers, meeting planners—and they require close attention to the nuts and bolts of the industry. Average travel enthusiasts might find some of it a bit dull. But you need to understand your readers (even when their interests are different from yours) and make everything compelling, relatable, and useful. Flexible meeting space? Fascinating. Hotel cleaning protocols? Love it. Airline codeshares? Nothing better in this world.

You’ll also need to master the concept of the press trip, those legendary junkets that take reporters off to the far reaches of the world.

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To outsiders, press trips might look like a free vacation. You’re flown to an exciting destination, checked into a luxurious hotel, fed gourmet cuisine, and toured around like a VIP. Friends, family, and followers only see your photos of lush swimming pools, shimmering beaches, and posh accommodations, so they could easily assume that you’re spending every day lazing on a lounge chair and sipping piña coladas. What most people don’t realize is that travel writers often don’t have time to dip their toes into the pool or lie back on the beach. Meetings and interviews with hotel and tourism officials often fill our days, as well as site inspections and tours that sometimes require participants to “ooh” and “ahh” over meeting rooms and half-built construction sites. Press trip schedules can sometimes be tiring, too, with early-morning wake-up calls and late-night dinners that last way longer than you’d like with people who may not be your first choice as dining companions. But in my opinion, it’s an exciting learning experience and it’s worth every minute.

9. Learn how to meet—and insult—celebrities.

When you’re a travel writer, if you’re lucky, you might even meet the occasional celebrity. I’ve shaken hands with Sidney Poitier, conversed with presidents of several Latin American countries, and kissed the cheek of Mexico’s former first lady.

Meeting celebrities is even more memorable when you accidentally insult them. At the grand opening party of a lavish resort in the Bahamas, for example, I failed to recognize a 1970s pop star and repeatedly asked him to get out of the way as I tried to take photos. I thought he was some random hotel guest.

“You want me in the picture too,” he assured me.

“No, I don’t, but thanks!” I said, laughing politely as I waved him away. Repeatedly.

He still didn’t move. He even told me who he was. I looked closer and suddenly recognized the eyes, the smile, the slimmer man inside. It really was him. I apologized profusely and took the photo. He was gracious about my mistake. “It happens all the time,” he said.

The point is, you should be happy when you get the chance to meet people of all backgrounds, and travel writing is a great way to do so—even if sometimes you don’t realize who you’re talking to.

Travel writer Mark Chesnut today, exploring the streets of Mexico City. His new book, Prepare for Departure, is out now from Vine Leaves Press.

10. Commit to being a trip whore.

If you’re passionate about being a travel writer, prepare to be called a trip whore. But don’t misunderstand. The term doesn’t mean that you have sex everywhere you go (although if you were truly following in the footsteps of some secret agents, you might).

Being a trip whore just means that you don’t know how to say no to a free trip.

I first learned the term when I started working for that travel trade publisher in 1994. The moniker seemed perfect for me.

I was ready to go just about anywhere. After all, I’d spent years building a career centered around my passion. Writing and editing were the only things I did fairly well, and traveling was, well, the most important thing in life, so why would you ever turn down a trip? (Oh yeah, my husband, family, friends, and other loved ones were more important, for sure. That’s what I meant to say. The intoxicating aroma of jet fuel that blew in from the tarmac at the airport temporarily clouded my mind as I wrote this).

An excerpt from “Prepare for Departure: Notes on a Single Mother, a Misfit Son, Inevitable Mortality and the Enduring Allure of Frequent Flyer Miles” (Vine Leaves Press, 2022)