Road Rules For Successful Cross-Generational Trips

05/28/2015 07:30 am ET | Updated May 28, 2016

Taking my 70-year-old-plus in-laws on a 1,800-mile, seven-day road trip had potential relationship calamity written all over it.

My in-laws' vacation history includes sit-down meals just 15 minutes into the start of a long day's drive, genealogy-inspired gravestone stenciling and anguished moans at missed shopping opportunities -- none of which I find comprehensible.

I wondered how three decades of strong in-law relationships would survive an excess of 50s music and Cracker Barrel consumption, particularly after my father-in-law let me know he had mapped every possible stop at those "Old Country Store" restaurants on our route.

Once the trip was gifted at Christmas, there was no turning back. We would travel from Chicago's suburbs to Washington, D.C. to New York City and back home in seven days.

The reward for me was time with my wife, who recently relocated for work to Long Island City, New York. For my in-laws, it was play time with the D.C. grandsons, drinks and dinner with three of their four children, the 9/11 Memorial, a couple of shows (Jim Parsons' play was a particular treat to diehard Big Bang Theory fan-in-laws) and a two-hour side trip to photograph a Brooklyn apartment complex my grandfather-in-law lived in during the 1930 census.

Somehow, it worked. While we didn't discuss rules before departing, several elements contributed to the trip's success:

  • Start on time. My mother-in-law deplores early mornings, but our schedule dictated several starts before 10 a.m. She was ready each morning to alleviate the peak of my schedule progress anxiety.
  • Don't cram the agenda. We broke the drive to D.C. in two parts, stopping overnight in Southwest Pennsylvania to tour Frank Lloyd Wright's stunning Fallingwater home before infiltrating D.C. evening rush traffic.2015-05-21-1432235282-859453-IMG_0590.jpg At the trip's other end, we drove 13 hours straight from Long Island City (stopping only for two sit-down meals). We made it, but were all strained when a bridge-work-based highway closure added 40 unexpected minutes to the very end of our trip.
  • Don't drink too much. I would have made interim restroom stops if my in-laws needed them -- something I've been accused by my wife and children of delaying or denying in the past -- but it made the driving much easier that we could go for three-hour stretches at a time. I also slowed my caffeine consumption, knowing that any stop would extend beyond my solo norm.
  • Adaptation works both ways. I don't eat sit-down meals when I'm taking long road trips. My in-laws enjoy multi-hour leisure events. We stopped for sit-down meals, but kept them to less than 40 minutes. I found myself appreciating the speed of Cracker Barrel's service (along with the oatmeal and meat loaf). When it came to music, I occasionally moved the dial to feed my news junkie preferences and we found a few stations playing music stretching into my era. After seeing the Jersey Boys musical, I even welcomed hearing Frankie Valli and the Four Seasons on the drive home.
  • Be prepared to drop off and walk less. Leg pain hamstrung my mother-in-law's distance walking ability and my father-in-law was hospitalized just before our trip with a racing heart, so I made sure to adjust the physical demands on them. During a night tour of D.C. memorials, we dropped off and picked up rather than parking and walking long distances. It was an honor to be with my father-in-law as he viewed the Korean War Memorial for the first time. It was also great to see how many people thanked him for his service after noticing his almost permanently attached Korean War veteran's hat.
  • Listen and ask questions. During the course of nearly 30 hours of driving, I learned a great deal about people I have known for three decades. I heard about a fascinating meeting with a communist mayor in Florence, Italy and more on family history that includes ties to some of Chicago's noted crooks and/or politicians. We talked about everything from bucket-list travel desires to pride in their children and grandchildren to how ISIS is replicating Armenian genocide and Holocaust horrors. We also went silent for sizable stretches, without discomfort.
  • When the driver scares you, close your eyes. Driving in and around Manhattan is as close to blood sport racing as public streets get in the United States. The intensity and incoherent decision-making of fellow road warriors is tough on those who rarely venture off suburban or rural roads. I managed, with ever-expanding aggression, to survive unscathed, but not without wrecked passenger nerves, slammed brakes and gunned engines. All this passed without complaint, for which I was grateful.

After a week of nearly continuous interaction, our friendship both survived and strengthened, with a multitude of new memories to fuel future discussions and the real possibility of enjoying future trips.

In the next couple of months, I'll take another East Coast trip, this time with my mother in the passenger seat as her Christmas gift. I expect the same success, following the same unspoken (though now written here) rules. This time, though, I'll add overnight stops driving both directions.

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