My Roman holiday taught me that pillows are not just for sleeping. They’re my coping method of choice, excellent at muffling frustrated screams while locked in the bathroom on a three-week family trip in the Italian capital.
I’ve done over a dozen multigenerational trips, from large reunions to birthday cruises and seaside anniversaries. Planning to avoid such moments — when you, the adult child, turn back into a sobbing five-year-old thanks to a triggering argument with your mother — is key to a successful family holiday.
Making golden holiday memories with the ones you love most requires someone to be the adult in the room, armed with strategies to avoid the pitfalls — about money, the itinerary, past grievances — and ensure that great experiences are created, instead of ones that belong in Dante’s circle of hell.
A multigenerational vacation usually includes three (or more) generations of family members, but there are no hard and fast rules on inclusion. When you’ve got a large group with wide-ranging ages (anywhere from newborns to 80+), differing physical abilities, financial resources, and interests, trip organization can become an overwhelming and stressful juggling act. Planning and patience are key to surviving a multigenerational trip and ensuring it goes as smoothly as possible.
Plan in advance, and think about who is going
Our most recent multigenerational trip involved celebrating my parents-in-law’s 60th wedding anniversary in the Belgian seaside town where they were married. We started planning the date one year in advance and worked backward on booking accommodation and flights, invitations, catering, the party venue, etc.
The organizational heavy lifting can be a group endeavor, but it’s best to appoint some lead planners or go outside the family circle entirely and hire a travel agent to handle the booking complexities. “Going pro” can ease the load and save time and stress.
It’s important to remember trip participants’ ages, interests, and limitations. Our Belgian adventure included teenagers and octogenarians, blind uncles, and frail aunts. We planned day trips and activities to do together and apart, and this made the trip better for everyone.
Separate accommodations are helpful, if possible
I chalk that success up to experience. My first multigenerational trip with my parents and kids was to Honolulu, Hawaii nearly 25 years ago. Two kitchen-equipped apartments within easy walking access to the beach meant carefree time with our then-toddlers, who were solely interested in sandcastles, ice cream, and little else.
The separate accommodations allowed us space and independence so we could plan activities (naps, couple time) separately or together with ease.
Patience — with yourself and each other — is key
It’s taken me a bit longer to figure out how to pack my patience — that key accessory so vital when traveling with others, when even the best relationships are tested by jet lag and ancient grievances.
Knowing the touchpoints that can trigger strong emotions and finding the patience and coping mechanisms — screaming into cushions, taking a walk — are necessary to cool situations that can ruin both vacations and family ties.
Talk about money before the trip
Conflict about money is one of the most contentious aspects of multigenerational trip planning. Unless you have a grandma or uncle with deep pockets, no one party is going to cover the entire cost of the trip. Honest conversations about who will pay for what — well ahead of the departure date — will help reduce arguments down the line.
Traveling with family is worth it. At its best, a multigenerational trip is an unforgettable opportunity to spend time with the people you love the most; for littles to enjoy priceless moments with grandparents; and for adult children to savor and foster relationships across generations. Just remember the pillow.
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