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The Art of the Trip

The first time I took my wife on a long weekend—an excursion to the Maryland Eastern Shore—I worried it might be a little bit of a test of our patience. Could we sit in a car for three or four hours and not get restless or argumentative? Would we agree on my suggestions of restaurants and lodging, or which places to visit? How would we handle possibly getting lost?

Happily, my concerns turned out to be unfounded. In fact, as I filled in my rough trip plan with spur-of-the-moment additions, like deciding it was time for ice cream or pulling into a neat-looking store, I almost felt like I was acting out a script. For example, despite never having done it before, I found that I was comfortable using my own judgment to narrow down the fire hose of information from review sites like Yelp and TripAdvisor. I knew how to pace our trip: when to be on the road, when to visit attractions, how long to spend at a museum or garden. I had a knack for spotting unusual or interesting businesses from the road. (Of course, it helped that she had plenty of patience with me.)

All of this might sound mundane or boring, but it is not necessarily obvious. Plenty of vacationers end up arguing, spending too much money, or simply being bored. The “script” I was acting out, I realized, was one I learned from my parents, from being a child in the back seat and observing dozens of day trips, road trips, long weekends, and vacations. I learned from them a certain way of traveling and seeing places, of ordering and organizing a day or more away from home in a delightful and relaxing way. Call it the art of the trip.

While this is not a travelogue, I will add that those childhood trips involved day trips to New York City and Philadelphia, shopping at outlet centers and new big-box centers in southeastern Pennsylvania and central and north Jersey, vacations from Maine to California, and long weekends in Washington, D.C. I fondly remember quirky attractions like Northlandz, Roadside America, and Peddler’s Village, places like Lancaster Amish country, and so many more. These trips were usually modest and avoided a lot of very popular, very crowded destinations.

I don’t claim that my parents’ way of traveling is the only right one, but it did cut out the crowds and stress of touristy vacations like Disneyland or a summer beach trip. We chose off-peak weekends, explored small towns and back roads, avoided most of the recommended restaurants and attractions that you just have to see, and simply learned to enjoy the relaxation of the trip itself and the variety of seeing an unfamiliar place. We found a way to improve our vacation experience and save money at the same time.

Each of these trips was like a data point, allowing us, albeit informally and mostly unselfconsciously, to iterate and optimize until the skills of trip-taking were well formed and habitual. It was this whole body of knowledge that I realized I had inherited as my wife and I drove peacefully around the Eastern Shore. 

This sort of thing is an excellent example of the idea of “privilege,” or unearned advantage. It is a privilege to have grown up in a family where I learned these skills. And they are skills. This is a microcosm of a broader point my colleague Rod Dreher has made—that many young people will fail to form families because they have never seen one modeled for them. The ease with which I planned my first long weekend was an example of this, in the sense that I had seen these things modeled for me, and learned them more or less by osmosis and without effort. Many young people do not. There are much more severe effects of the breakdown of the family, of course, than never picking up tips for a great vacation. But learning the attitudes and dispositions that allow for pleasant time away is a good thing. And taking a trip isn’t just about travel. It in turn requires many of the same habits and dispositions that make family life pleasant. 

Some of these things are a bit on the abstract side. Traveling is an excellent way to realize the insight in the idiom “penny wise and pound foolish.” You get what you pay for—but you also get a lot that you don’t pay for. Over time, and as my parents’ income increased, my family learned that it is usually worth it to spend a little bit more up front as insurance against problems that might ruin the whole trip or add unforeseen expenses. For example, $30 extra per night for a hotel room can help avoid a noisy, musty, or bedbug-ridden room that will keep you up or make you sick. Seeing beyond the price tag and understanding value tradeoffs is a real financial and life skill. There’s a sweet spot where you’re paying for all the cleanliness and amenities you need, but not being gouged because of a place’s touristy reputation.

There is, of course, a class element to this: poorer people may not be able to afford the better option because they simply do not have the extra money now, even if their total expenses end up higher, or if their experience ends up worse. People who can afford a more nuanced and longer-term approach to spending, however, should probably practice it. 

Beyond money, successful trip-taking requires thorough preparation and planning, down to the level of a night-before checklist for grabbing items and loading the car. It also requires time management, and enough self-awareness to plan a day without getting tired two thirds through. 

It is a wonderful feeling, as you grow up, when you realize that you don’t need anyone’s permission to peruse the map and book a hotel. But to make the most of this freedom it is also necessary to form mature habits befitting an adult.

Trips can be edifying and can reinforce these good habits, and also provide motivation for their practice every day. I’ve found that one piece of advice helps me to work hard and watch my spending on a daily basis: always be planning a trip. They don’t have to be lavish; they’re usually long weekends or overnight stays in quaint small towns or interesting cities within a four hour radius or so. But that’s enough, and it provides a regular way to practice and reward delayed gratification.

Working a real job and holding down the fort is an essential element of adulthood. But learning how to pleasantly escape it is certainly another. I was very lucky to have learned this in my childhood, but it is not impossible to learn later in life. Pick an affordable, under-explored spot on the map, and get started.

Addison Del Mastro is assistant editor for The American Conservative. He tweets at @ad_mastro.

about the author

Addison Del Mastro is assistant editor and social media manager of The American Conservative.  He is a graduate of the University of Maryland School of Public Policy and writes on urbanism, place, and popular and cultural history. Follow him on Twitter at @ad_mastro.

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