How to Ruin a Multigenerational Trip in 5 Steps — and How to Fix It

Mishap 2

You pack the itinerary with such anticipation it drives travelers of varying ages to near mutiny.

We hadn’t wanted to provoke testy exchanges and sullen moods among all generations throughout the demanding two-week itinerary. But there was a reason for our overenthusiasm that extended far beyond COVID “revenge travel.”

For starters, both family trees boast several Gaelic surnames, including McRea (my mom) and McCullough (my husband’s grandmother). It wasn’t surprising then to learn from our kids’ DNA tests that they’re predominantly Irish (more than 30 percent ethnicity each).

Ireland was my in-laws’ favorite country, a place they’d visited a dozen times, including with my husband and me on our first trip there in 2003. We had always planned to return someday with our children and their grandparents.

My father-in-law died unexpectedly in 2016, months after he and my mother-in-law returned home from Ireland. In our quest to honor his memory, we heaped on activities and travel, rushing from place to place, activity to activity, and adding stress for all generations, age 14 to 78.

What I should have done: Abandoned my too-high hopes for our heritage vacation and selected fewer destinations, or we should have limited the trip to one week. In essence, we could have lingered at a spot for a few days as travelers instead of checking off boxes as tourists.

If the day starts too early, children are tired, and everyone is bound to be miserable.

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Mishap 3

You stay at each spot for only a day or two, and everyone can grumpily repack their luggage again and again. Even worse? You start each day of vacation around 8 a.m. to relive the hellish chore that is getting kids ready for school, particularly teenagers.

That smacking sound? An entire palm to forehead as I ask, “What were you thinking?”

In fairness, we originally booked the seven-day train and bus trip to fit the kids’ one-week spring break. It wasn’t an ideal itinerary for our sons because teenagers in general are tiiiiiiiiiiiired. (We’re also night owls, so the four of us are allergic to early wake-up calls.) But the option allowed maximal sightseeing without driving ourselves, as we did in 2003, when my father-in-law negotiated the opposite side of the road. (Zero stars. Would not recommend.)

Even one week of frequent destination changes proved intolerable for everyone. The boys legitimately tried to get up and leave on time each day, but many days included five to 10 strained minutes of fretting and foot tapping by super time-conscious grandparents. It’s been decades since our moms had to get teens out of bed and to school on time, so they’ve forgotten the struggle (probably by design). Grandparents are typically accustomed to arriving at places on time, even on vacation. Surliness for all seven of us ensued.

What I should have done: Avoided setting up my sons for failure, no matter their herculean efforts to leave on time. Instead, we should have stayed at each spot for a minimum of three nights. We would have explored only half the destinations but with fewer hassles.

Mishap 4

At the start of the journey, you add an ambitious leg to an entirely different destination; for instance, jetting to Iceland.

When you realize you’re flying via Icelandair, which allows transatlantic travelers a free stopover in Iceland for up to a week, how can you say no to three nights in Reykjavík?

On our first Iceland visit in 2016, the boys had been too young to explore the iconic Silfra fissure, the only spot in the world where you can dive or snorkel between (and actually touch) two tectonic plates. Now old enough to fit into the required dry suit, the boys could join us while our parents toured geological wonders we’d already seen.

While we were there, we thought, Why not also book a tour that descends into the only accessible lava chamber on Earth? It’s named Þríhnúkagígur, or “Three Peaks Crater” — I have no idea how to pronounce it, but dropping into the belly of a volcano via customized, open-air elevator is as magical as it sounds.

What I should have done: Avoided the temptation to add flights and adventures at the beginning of the trip while travelers were fresh. The more you fly, after all, the greater chance there is for a cancellation or lost luggage and so on. Though we could have tacked the three days on an easier itinerary, another leg merely added fatigue before the primary trip even got started.

Mishap 5

You remain past the end of the itinerary, so the original one-week plan expands into two.

News flash: No one wants to stay a few more days after crisscrossing a country for a week straight, no matter how many times you convince yourself otherwise. Remember, the kids’ social networks become increasingly important with age. So FOMO (fear of missing out) for teens is real, even for one week.

My mom and the boys wouldn’t have gotten to enjoy Dublin’s famous pubs and tourist spots unless we’d stayed some days on either side of the Railtours excursion. Except we’d already blundered so much by trip’s end that sightseeing had long since lost its luster by Dublin. Not even the hard-to-book tour of Ireland’s historic symbol of independence, Kilmainham Gaol (jail), could soften our collective desire to return home.

What I should have done: Booked only one night in Dublin and flown home as soon as the main itinerary ended. Not one of us wanted to stay another day or tour another museum after traveling for nearly two weeks.