Staying for extended stretches in exotic and culturally rich places for free? Then being paid for pieces you’ve written about your stay? Sounds unreal, but the reality is anything but: over the past several years I’ve spent one- to two-month periods in Hawaii, Mexico, Panama, the Bahamas and St. Vincent and the Grenadines with my sweetheart Alice, without paying a cent for lodging.
With some careful prep, and an open eye and mind for stories when you get there, you can set yourself up for exciting travel—and even some green from writing about that excitement.
Finding the Opportunities
For the past few years, mindmyhouse.com has been our house-sitting site of choice. The site provides descriptions and photos of the properties, dates and length of stays, and what the homeowner wants you to do in exchange for staying at their home.
MindMyHouse emails listings almost daily, and they are truly from all over the world. Some owners want you to do things like manage multiple Airbnbs or groom their herd of buffalo, but most of them want someone to take care of pets, water plants and keep the house secure.
The Net, Cast Wide
To be doable, you have to have work that allows you to leave your house for relatively long stretches of time. The Internet has opened the floodgates for such “solopreneurs.” Both Alice and I have been freelancing out of our home for years.
Of course, house-sitting means someone probably has to take care of your home as well. We have a cat who needs attention, as well as a garden, and we’ve found house-sitters on MindMyHouse who have done fine jobs. We wrote a small manual of the idiosyncrasies of our house so that there aren’t any surprises and have made sure the bills are set up to be paid in advance.
One sour surprise is when the Internet is spotty in the house-sit home, or worse, out for days at a time. That’s happened to us in the Bahamas, and that didn’t help with some deadlines. However, that does allow for time to engage in travel writing.
Look for Angles, Before, During and After
Look for story angles in advance to see if there’s any editor interest. I pitched stories about biking to the lava flow on the Big Island and on things to do in Hilo before we spent time there, and later had the pieces published in the Los Angeles Times and the San Jose Mercury News.
At the same time, it’s smart—and fun—to be open to story ideas that crop up. When we stayed in the Grenadine Islands, we found out that there’s a rum distillery on St. Vincent and took a private tour there. Haven’t placed that story yet, but I did place a fun one on looking for whiskey on an island of rum.
Always have your camera at the ready when you’re out and about, as you’re likely to find sights for your lenses that most short-visit tourists wouldn’t.
And I never travel without a notepad, making sure to type up my scrawled notes about people, places and things within a day or two of scrawling them, when my memory is fresh.
Your Office Is the World
Even if you have to take care of ill or psychologically-damaged pets (a couple of times for us), or a psychologically-damaged owner (once, and that was enough), the opportunities for travel writing as a house-sitter are deep.
House-sitting puts you in a great position to see splendid sights—and then set them on the paying page.
BIO: Tom Bentley is a business writer and editor, an essayist, and a fiction writer. He’s had hundreds of freelance pieces published—ranging from first-person essays to travel pieces to more journalistic subjects—in newspapers, magazines, and online. His self-published book on finding and cultivating your writer’s voice, Think Like a Writer: How to Write the Stories You See was published in June of 2015. You can see his lurid website confessions at www.tombentley.com. Mr. Bentley would like you to pour him a Manhattan right at five.
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