Multi-Generational Travel With Family

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Bringing order to chaos and stamping out small fires as they occur in the emergency department turn out to be great preparation for family travel. It’s like any other shift, only it stains your regular clothes.

As I write this on a plane in mid-June, we have just completed our second multi-generational family trip of the summer.  The goal was to allow grandchildren, adult children and grandparents to create memories of shared travel experiences together.  Now it’s time for the post-game analysis.

The wife and I prefer the to call family gatherings like this “trips” rather than “vacations” because most travel with kids seldom provides sufficient relaxation to qualify as vacation, although there are happy moments amid the bedlam.  

Before any critique commences, I should openly acknowledge that it’s a wonderful privilege to enjoy the protected time, health, resources, and close relationships that allow family trips to be an option. We either like each other enough to want to spend time together outside of holidays, or want to make each other happy enough that we’ll suck it up and take one for the team to please those who share our genes.  Often it’s all of the above.  My wife has likened these trips to labor pains – we tend to rapidly forget any hurt and selectively recall only the positives in time to plan the next trip.

For those of you fortunate enough to be negotiating similar trips with your families, it’s hard to find a place that can capture the imagination of multiple ages and stages.  Our group included these categories: single, married, overwhelmed with your own kids, overwhelmed with other people’s kids, overwhelmed with physical limitations, overwhelmed with anxiety.  All of us are control freaks.  Squeeze us all into an airbnb and you might assume we comprise a recipe for certain disaster until we reveal our secret: the key to happiness is low expectations.  Expect a challenging trip with fun moments and you’ll be pleasantly surprised at how many moments you enjoyed.  Expect a bonanza of fun without challenges and you are bound to be disappointed.

The negotiations over what type of trip to take were fraught with everyone’s personal baggage. As parents of young kids, we wanted to visit places with a distinct culture that we could experience and learn from while also having experiences for the kids.  The younger single people wanted someplace fun with nightlife that wasn’t entirely kid-oriented or geriatric. My parents, trying to please the varying constituents, suggested a cruise.

About cruises: they’re not my bag, baby.

I have taken a couple, and I’ve concluded life is too short to repeat the experience. Cruises take an ostensibly enjoyable experience we value, travel, and strip away most of the aspects we love about it: the opportunity to interact with locals off the beaten path; the ability to limit or avoid commercial interactions; the freedom to take risks and make last minute itinerary changes on a whim; housing that minimizes the walls separating us from locals; and the freedom to seek out traditionally prepared local cuisine in mom and pop eateries. (If you share my feelings, may I suggest you read the late David Foster Wallace’s brilliant essay, “A Supposedly Fun Thing I’ll Never Do Again“).  Ultimately, we nixed the cruise idea in favor of a family heritage trip.

Trip #1: Mexico City
The first trip was a rediscovery of our family roots in Mexico City with my side of the family.  We visited the site where my late maternal grandparents where married, took a walking nostalgia tour of the neighborhood where my mother experienced her formative years, and saw the cousins she grew up alongside as a child.  It was wonderful.

One adaptation that proved valuable was starting with reasonable expectations and limiting our ambitions.  We decided the prior evening what time we’d meet for breakfast the next day, and what single morning activity we’d pursue together.  One day it was a trip to nearby Coyoacan to visit Frieda Kahlo’s home with Diego Rivera.  Another day it was an open air double decker bus tour that dropped us off in the historic downtown to visit Aztec ruins and wander through colonial neighborhoods.

Another key to the happiness on this trip was that we assessed our housing options early, booking two reasonably priced but luxurious condos to house six adults and two kids. Each had a full kitchen and fridge to facilitate snacking.  The condos were a short walk from restaurants, bakeries and coffee houses centered around a European-style plaza in the rapidly gentrifying neighborhood Roma Norte.  The kitchens and proximity to breakfast meant we never started our days hangry (hungry-angry).

The strategic housing also meant everyone had a separate space to retreat to when the need arose, allowing us to decompress and appreciate one another all the more when we reconvened for dinner. When our kids needed some wearing out, we took them to the pool at our condo and let them fatigue their little hearts out while my wife swam laps, their grandparents napped and their aunts shopped.

Trip #2: Portlandia
The second trip with my wife’s side of the family was to Portland, Oregon.  We settled on Portland because it was conveniently near the family with the toddler while also appealing to the rest of us.  It promised novel attractions, ubiquitous reasonably priced and delicious food, a well-appointed place to stay in a walkable neighborhood and a reputation for allowing eccentric dreamers to thrive (we thought we could help keep it weird!).

For this trip, we rented a single large airbnb together in the Alberta neighborhood.  The drawback of this arrangement was it put the toddler’s parents (early wake up times, earlier bedtimes) in a tough position since they stayed in a room within earshot of a common area where most of us stayed up after they were in bed for the night.  When my nephew developed an upper respiratory infection, it meant neither child nor parents slept particularly well.  In retrospect, providing them a separate housing option would have offered more flexibility at the cost of less accessible babysitting.

The benefit of staying together was that when the toddler went down for his second nap of the day in the afternoon, we adult children lovingly pulled a “dump and run,” leaving the sleeping toddler and both my kids with the resting grandparents while the two sets of parents hit the local happy hours within walking distance.  We’d return to universal delight with a new interesting take-out dinner from a local food truck or locavore diner.  Everybody won.

A second benefit of staying under one roof is that, for the grandparents, even the in-between times spent together seem to have real value. Being bored together was preferable (in their eyes) to being bored apart.  So despite the usual challenges of lots of people in close proximity, the ability to compromise to make aging parents happy was one more small victory.

As our own kids adopt preteen mindsets (and the sometimes defiant behavior this can entail), these trips make us acutely aware of the dimension of modeling that we are providing for our kids.  It won’t be long until we are the aging parents, they are the busy young adults, and our requests to spend time together are met with grimaces and grumbles.  Best to demonstrate how we can compromise and make our parents happy while we all still possess the health and mobility to share these experiences together.

You may ask yourself, “In what ways does my adult relationship with my parents reflect a model I’d be proud for my kids to emulate? ” You may ask yourself, “How did I get here?”

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