• Over the last 25 years, I've been on over a dozen multigenerational family vacations.
• I've learned planning early and keeping the limits and interests of those going in mind helps.
• It can also be helpful to book separate accommodations if possible.

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.

• Whenever we're with my mother-in-law, she asks my son and daughter-in-law when they'll have kids.
• While some part of me likes the idea of being a grandparent, I don't mind if it never happens.
• Ultimately, I know it's not up to me.

Without fail, every time we get together, my dear mother-in-law asks, "When are you having children?"

The question is not addressed to me. I have two sons, now in their early 20s. My younger son is married, and the query is always directed to him and his wife. My daughter-in-law and I exchange a look, and before she can answer, I pipe up with, "Not for a while, I hope."

My kids have time to figure it out

The truth is, when my wonderful son and lovely daughter-in-law got married three years ago, I asked them to pinky swear that they would not have children for 10 years. Of course, this is not my call to make, but as they tied the knot at 21, it certainly seemed like a prudent pact. They are young, have lives to live, careers to form, and trips to take. There's time.

I also swore I would not ask them about having children and have since kept that promise. Part of my hands-off approach is out of respect for my children and where they are in their own lives, adulting in their mid-20s, still figuring things out. But the other reason is a personal one that looms larger every day. Though I've heard being a grandmother is great, and friends who are living that reality are certainly happy, I've never dreamed of becoming a grandmother.

For years, my innermost thoughts and feelings about my children producing their own offspring have been conflicted. It's not out of concern that they wouldn't make good parents — they would. My internal struggles orbit around whether the world as it will be really needs more people. I'm not sure it's such a great idea.

My belief systems are no longer rooted in the religious or patriarchal notions of my youth and upbringing, which held that it's our duty to continue the species, to go forth and multiply. The reality is that there are already more of us than our blue marble can handle, and we're ensuring that the climate crisis will make living on it even more challenging, particularly for those with the least ability to cope.

I don't mind if they never have kids

Some part of me likes the idea of grandchildren, given how my own life has been enriched by having kids — something I want for my own children, if they want it. But I'm also kept up at night by larger worries about environmental challenges and adversities to come, which are concerns that go beyond the usual parental angst over a child's health and future career paths.

I tend to see the glass as half full rather than empty, but I worry about how my potential future grandchild will navigate the road ahead. In that, I'm sure I'm like every other parent, wishing for a crystal ball to allay anxieties and lost sleep over what cannot be foreseen or controlled.

At the end of the day, the choice will not be mine, it will rest with my children. No matter their decision, I won't be the one to pressure them one way or the other, and it will certainly not make me love them any less fiercely than I already do.

Whatever comes to pass, so be it. Right now, I'm OK if the line ends.