Two premises: (1) you want to write and sell something about a coming trip, and (2) you want to be able to keep all of the money you earn, or at least increase your IRS tax deduction as much as you can.
Good thinking—and totally legal. You are supposed to take every deduction allowed. More than legal, it’s patriotic!
If your writing is a serious business venture (not a hobby), even if this is your first trek in that forest, you must act business-like. That includes writing something and sending it to one or many possible buyers, probably magazines, newsletters, or newspapers. That is, you can’t write off expenses or income if you don’t offer any writing for sale!
Let’s set up an imaginary trip so it’s easier for you to imagine and follow the steps. Let’s go to San Francisco!
First figure out how many days you will be at the target site and how many specific topics you will have time to write about. Imagine you will be in San Francisco for five days and you want to write (1) about the ferry trip to Tiburon and Angel Island, and (2) a trip from Fisherman’s Wharf to Alcatraz Island (and back!).
First, go to your computer or library and gather up lots of facts about both. You will need facts, quotes, and anecdotes, plus some sharp digital .jpg photos. Too many facts and photos are far better than too few, and if you see some first-rate quotes in print make a word-for-word copy of those too. (Live quotes you gather on site are much better.)
Now find something you want to focus on at each location that will make your article unique and informative. Say for (1) the newly opened immigration camp where thousands stayed en route to the U.S., mostly from Asia, and (2) retell the “Home of Al Capone,” plus what one sees on an Alcatraz visit today.
Next, find, say, three magazines that might be interested in Angel Island and three for Alcatraz, and put them in order (probably by how much they pay). Create one prioritized list for Angel Island, another for Alcatraz. Then read the first magazine on each list so you know what the respective editors are looking for.
What you must do then is write a fetching one-page query letter to the editor of each of those magazines, bringing the topic alive and asking (directly or by implication) if they would be interested in reading your article after you return? Give them an approximate return date and promise the article in three weeks.
To be able to deduct expenses later, the single most important thing you must do before going is writing and sending pre-trip query letters. Whether the editor says yes or no, the letter before the trip shows the intent of your trip. Keep a copy of the letters, of course, and the replies. (If the first editor says no, then query the second editor, and so on—but only one at a time about each topic.)
Later, all of the article-related costs will be deductible, so keep receipts or credit card info. That includes travel, hotel, ferry fees, excursion cost to Alcatraz. Almost anything except food (you have to eat anyway). The submissions needn’t be bought by the editor either.
If you’re serious about this and you want to be in print as often as possible, you can rewrite the magazine articles that do sell, query other editors, and sell to them. After you return, create some newspaper pieces too (1250 words or so is a good target length) and sell those simultaneously to any regional newspaper at least 100 miles away from any other that you are also contacting. No query needed here, and do these after you get back. (These articles must be different from your magazine submissions.)
If you sell, say, two magazine articles ($250 each) and four newspaper pieces ($100@), that’s $900 you know you can deduct, if your expenses are $900 or more. You can only deduct as much as you spend on the articles; if you earn more, welcome to the taxpaying majority!
What if you don’t sell anything? As long as you followed the query and submission protocols, you can still deduct what you expected to receive had they sold. Uncle Sam will let you short-earn a few times before they call it a hobby. That’s because once you get professional, you will often earn many, many times your costs on every trip.
I’ve skipped through the details here simply to give you a timing tip that will make trips elsewhere deductible. Please read the Travel Writer’s Guide where the rest is all spelled out.
Incidentally, if you do visit Angel Island, take the bus trip around, get off at the immigration camp, and just walk the short distance back to the pier. It’s long poke around the island on foot—and very hilly.
If you’re a newcomer, welcome to the travel-writing club! (See the many related blogs about freelance writing at this site.)