How to plan a multigenerational family trip

The first sign of trouble on our family trip to Italy was at a drawbridge in Delaware.

My brother and his girlfriend were aboard an Amtrak train from D.C. to Newark to meet my parents for a flight when they hit an hourslong delay: A yacht club had requested the bridge be held open for an event. They missed their flight, forcing my parents to travel alone on their first trip to Europe — something we had planned meticulously to avoid.

Meanwhile in Italy, my boyfriend and I were driving a rental car to the Rome airport on an almost flat tire. White-knuckled and holding my breath, I began to question everything about the trip. Had we taken on way too many logistics? Would my family of six still love one another at the end? It was far from the idyllic start I envisioned — easy flights, refreshed travelers embracing one another at the airport, carbonara for lunch together on a piazza in Rome.

Multigenerational family trips can bring some of life's most cherished moments — but also some of the most stressful. You're wrangling various levels of stamina, budgets, interests and eating preferences, not to mention trying to get everyone to one place.

"At the end of the day, it's not your personal trip," said Lauren Doyle, president of the Raleigh-based agency the Travel Mechanic.

My family has taken dozens of trips together, but this was by far our most logistically challenging. We came away with many lessons, including how much we actually enjoy traveling together.

Set realistic expectations

Doyle said the first thing she does when planning a trip for a group is to get someone representing every age group to identify their goal for the trip. There are often multiple group chats or email threads happening at once, she said, so getting everyone on the same page is key.

"What do you want to accomplish? And then work backward from there. Is it a villa experience? Is it about researching family history?" Doyle said.

Sandra Weinacht, who runs the tour company Inside Europe Travel Experiences, said her first rule is to be brutally honest about your group. Your family members aren't suddenly going to be new people on vacation.

"If you know your sister doesn't get out of bed before 11 a.m., don't think she's going to get out of bed earlier on that trip," Weinacht said.

My very wise younger brother said to me in the weeks before, "I'm prioritizing relationships on this trip," and it really stuck with me. We'd probably never be back in this place as a family again, and making the most of it for our parents was our joint goal.

Figure out a budget and who's paying

Just because mom and dad are on your trip doesn't mean you've suddenly become a child again. Set clear expectations on what you're willing to spend and who's paying for what.

"Planning ahead and really thinking about how much money we have saved and who is paying is an important piece of planning," Doyle said.

In addition to booking most of our accommodations and tours, I suggested we designate my credit card for expenses (selfishly, I wanted the points). I kept track of expenses and told everyone what they owed when we got back home. We were actually surprised at how little we spent.

Find accommodations that suit everyone

If people aren't sleeping well, it's sure to creep into other aspects of the trip, Doyle said. So make sure you find a rental with enough beds (no one wants the couch) or a hotel with enough separate rooms if you know sleeping under one roof will cause conflict.

"Making sure you find accommodations that fit everyone's needs is really important, especially when you are dealing with babies or people with mobility issues," Doyle said.

Weinacht suggests finding somewhere to stay close to the center of the action to make things easier for a group. While staying farther out could save you a few dollars, it may not be worth the hassle or cost if you'll have to coordinate transportation for everyone.

Break from the group for meals

Not every meal needs to be eaten together on a family trip. In fact, both Weinacht and Doyle advise against it.

"Food is a huge thing people fight over," Doyle said. She suggests picking one "dining experience" for your trip, whether that's a cooking class, a dinner with a view or bringing a private chef to the house. Doyle said she always builds breakfast into packages for her clients because it's one less thing to think about in the morning.

I learned on our family trip that adventurous eating varied on my family's list of priorities. Some want the comforts of home sometimes; others wanted to try a restaurant they've been seeing on a list.

Build in alone time

We set aside "alone" time on our trip in big and small ways. First, we knew everyone had different bucket-list stops. I wanted to go to Sicily; my brother wanted to see the Amalfi Coast. Plus, there was no way we could tackle all our goals on our PTO and financial budgets.

So we bookended our trip with our own agendas: My boyfriend and I toured Sicily while my family would arrive a week later to do Rome, Tuscany and Florence together. We then escorted my parents back home while my brother and his girlfriend headed south. Everyone accomplished what they wanted.

We also planned a few hours of alone time for everyone each day. As Weinacht noted: "Having that time apart brings you closer because you come back together and share those moments with each other."

Don't overplan

When you have so little time in a place, your knee-jerk reaction is to jam in as much as you can. Who knows if you'll ever be back? As someone who loves a plan, I had to resist this urge.

"I always tell clients yes you can be a Type A planner, but you do not want to overplan on a multigenerational trip," Doyle said.

That's because these types of trips tend to be slower paced, she said. You may be traveling with elderly family members or kids, and their needs are different.

We built our itineraries around one big activity for the day and left the rest open for dining and wandering.

"You need time for those serendipitous moments," Weinacht said. "Leaving more time for yourself doesn't mean you are going to do less."