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As a travel writer who has adventured with my sons since they were babies, I am loath to describe any family vacation as ruined, terrible or even stressful. Whether getting dirty on a
backcountry biking trip in Wyoming or cruising through the Mediterranean, to me, there’s no better way to educate kids than by exposing them to the unique history, culture and food of any
destination away from home. But every so often, a vacation just feels a little off. Maybe it begins with a missed flight connection that delays you for a day or two. Or perhaps there are
several mishaps — lost luggage, broken-down rental cars, bad weather — that hamper travel plans and leave you asking: Why did we _ever_ leave our house? Or maybe you forget your best
planning advice — keep itineraries and activities as simple as possible, for example — and nearly break your family. According to an AARP study, about 14 percent of travelers 50-plus planned
to take a family or multigenerational trip domestically this year, and 13 percent of surveyed travelers planned such an international trip. A two-week vacation in summer 2022 — half of it a
seven-day Railtours Ireland All-Ireland Tour, with my husband, our two kids (then 16 and 14), both grandmothers and my mom’s husband — almost ruined us. Initially scheduled for one week in
March 2020 during the boys’ spring break, it took two years of waiting for the world to weather the COVID pandemic before we rescheduled. Our fervor to reclaim some of what we’d all lost
amid uncertainty inhibited any ability to follow my own Travel 101 advice. Of course, we had a great time in Ireland kissing the Blarney Stone, listening to street music in Galway and
setting foot on the iconic basalt columns of Northern Ireland’s Giant’s Causeway. But we did so with a schedule overpacked with early mornings and too many hours on a bus or train, adding up
to a lot of conflict and anxiety. Good news: We are still speaking to one another, and our recent cruise together was relaxing enough to sidestep even the tiniest squabble among us. Learn
from my family’s planning mishaps for a mostly frustration-free multigenerational vacation, especially for the kiddos. MISHAP 1 After a significant lapse between vacations — due to, say, a
pandemic limiting travel — you abandon your most basic strategy in planning family travel. If enough time passes between adventures, constrained perhaps by lack of funds or school calendars,
even experienced travelers can forget that overscheduled kids are unhappy kids. And teenagers are an exceptional brand of unhappy. (Adults aren’t much better, as it turns out.) My husband
and I are hyperactive, so reading by the pool was never on any pre-parenthood itinerary; we had to do all the things! We adapted quickly with our littles, enjoying slow-paced beach
adventures filled with unstructured fun such as playing in the sand and chasing waves, pausing only for food and sleep. As the kids grew older, downtime was necessary for basic survival —
the difference between a fun day of adventure or a full-blown cage fight between brothers at the hotel. Now they’re teenagers who mostly get along, so it’s easy to forget they still need to
decompress. Fortunately, my kids have offered me a lifetime of reminders that their childhood angst, once reserved for each other, becomes unmitigated teen irritation for most adults,
chiefly Mom and Dad. I can’t blame them. WHAT I SHOULD HAVE DONE: Broken up our busy itinerary with at least a couple of unscheduled afternoons or “on your own” days.