Maneuvering Family Vacations With Adult Kids, Grandkids and More

When it comes to travel, writer Janey Womeldorf knows her way around. She has worked as a tour guide in her native Bath, England, and as a travel agent in Germany. Now, as an Orlando, Fla., transplant, she's the in-house theme-park planner for her extended family. Over the last decade Womeldorf has coordinated family trips that include toddlers and  adult children as well as grandparents.

While family vacations can be a wonderful chance to reconnect, they can also be a time bomb of too much togetherness and too many expectations. Even a stay at a relative’s home or a low-key summer house can set off tensions. And the ante is raised when the vacation is a pricey theme park or cruise.

Womeldorf has organized a half dozen cruises for a group of up to 16 relatives and countless trips to the Orlando theme parks. She shared some of her tips with us, including a unique way to handle whining, her No. 1 pet peeve. Any sentence that begins with “I hate …” constitutes whining. Also under that heading are complaints ranging from “I’m tired” to “I ate too much.”

She came up with a clever antidote a few years ago when she bought a Jamaican-style wig as a souvenir and nicknamed it “Wiggy.” Soon after, she and her family instituted a rule: The person who whines the most that day wears Wiggy at dinner. While the wig has been worn multiple times, it certainly has helped lighten the mood overall. “If people whine now, they more often do so behind closed doors and not in the group,” she said.

The Wiggy wearer is chosen (or not) at the daily predinner gathering, another Womeldorf ritual. The family gathers at a child-friendly bar at 7-ish to catch up on the day’s activities. The meetup goes hand in hand with another rule: The family does not have to spend every waking moment together. “It’s important during the day to let everyone make their own plans, but then to create a gathering daily prior to dinner to get together and share,” she explained. Her rationale behind a predinner meeting is that it’s a better time for sharing rather than when ordering food and eating, and often a large group is not seated at one table.

Womeldorf suggests a similar strategy for theme parks, except family members meet for lunch. “I wear my pedometer and you can walk five miles easily in a theme park. While that’s nothing for teenagers, the grandparents may be ready to collapse,” she says. So when the young adults beeline to the thrill rides in the morning, the grandparents bail at a certain point and gather with the group for a late lunch at a designed park restaurant. Or the grandparents head for Dumbo with the little grandkiddies, allowing millennial parents to try the Tower of Terror, and then all regroup at lunch.

In addition to no whining and giving everyone time to explore their own activities, Womeldorf adds “matching expectations with reality” to her trio of rules. Whether it’s a cruise or a theme park, before the trip she outlines the details and options so there are minimal surprises.

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The night before a cruise, for example, her family gathers at a local hotel near the port for a party. “People have different activity and energy levels and budgets for excursions, so we go over the options,” she said. “And we pull out Wiggy as a reminder and get everyone in the mood.”

Mary W. Quigley’s blog, Mothering21 ,  tackles parenting of emerging adults and beyond.

Photo:  gregobagel/iStock

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