Understanding what drives the family vacation

The poet John Lydgate once (paraphrased President Abraham Lincoln and) wrote that you can’t please everyone all of the time.

Both men might as well have been talking about family getaways.

Think about it. If you take the kids where you think they want to go—a special children’s museum, for instance—you might find yourself daydreaming about stuff for adults. If you take the kids where you want to go—maybe a road trip to Frank Lloyd Wright’s Fallingwater home—they’re the ones who potentially could be bored out of their minds.

In recent months, with environmental and economic forces conspiring to change certain stores and beaches forever, some parents might even feel pressured to make sure kids experience the same stuff mom and dad did in younger days—before it’s too late.

The bottom line: Identifying what inspires your family excursions is a process. It takes time. It takes practice. And it can help you take more fulfilling trips for everyone involved.

In our family, we’re still figuring things out. To this point, the best trips of the bunch have been those journeys that have offered something for everyone: a few hours at the kid-friendly theme park, an adult-oriented visit to a winery, a pilgrimage to an old-favorite bar slated to close.

We’ve arrived at this realization the hard way, through a long (and sometimes painstaking) process of trial and error. That weekend we built around the new exhibit at our favorite modern art museum? A swing and a miss (translation: the toddler lasted an hour, then a tantrum prompted us to bail). The weekend we split time between the public playground and that open-air folk music concert? A much better showing (translation: she played and danced until she passed out both nights).

As we prepare for our next big trip—we leave Saturday for a month in Hawaii—we’re busy crafting itineraries that appeal to everyone—our 3-year-old, our 8-month-old, and us.

We know what’s at stake; inevitably, at least one Villano likely will take issue with parts of every plan. Our ability to find balance will make or break the vacation, and contextualize the memory for years to come.

What drives your family vacations? Please share your thoughts and insights in the comment field below.