“Brandi always thinks about the different needs of everyone,” says Ewing, of Duluth, Georgia. “What people like to do, their budgets and schedules—she makes it easy for people to say yes, bringing us all together.” Starr’s survey comes via email or text. Or in the case of the technologically challenged, a phone call. A few sample questions:

▶︎ Where would people like to go?
▶︎ Will they be traveling with other family members?
▶︎ What’s their budget, special needs and desired dates?

There’s a deadline for feedback—typically two weeks. Recipients who fail to respond can still go on the trip, but they’ve forfeited the opportunity to express opinions. So far, the surveys have resulted in two multigenerational trips. An upcoming cruise has also been planned, with 19 travelers.

Starr, of Suwanee, Georgia, views all this as a labor of love. “If you look at older generations, they tended to live closer together and naturally had traditions that were passed down,” she says. “But with more family living apart, some of those traditions fade, and the bonds that used to be a given—between cousins, grown siblings—aren’t always as strong as they could be. Travel brings us together and lets us make memories. It reminds us of what is truly important.”

Multigenerational travel—with groups that encompass three or more generations—is more popular than you might realize. A recent survey shows more than 40 percent of grandparents are likely to take such a trip within the next three years.

But just as travel can promote family togetherness and a shared sense of adventure, it can also provoke anxiety and sometimes tension.

To maximize the opportunities and avoid pitfalls, we assembled a panel of experts on this topic to guide you through this potential minefield and leave everyone in your family eager to embark on the next great vacation.

▶︎ BRANDI STARR, a frequent multigenerational vacation planner and marketing executive

▶︎ DEEDEE MOORE, founder of the grandparent advice website More Than Grand

▶︎ KIRSTEN MAXWELL, founder of the popular blog Kids Are a Trip

▶︎ EVITA ROBINSON, founder of Nomadness Travel Tribe, a community for travelers of color

▶︎ ROB TAYLOR, founder of the LGBTQ family travel site 2TravelDads

▶︎ GAYA VINAY, independent travel adviser with Fora Travel

STARR: I’ve learned to start trips with an online survey, and I always learn something I wouldn’t have thought to ask—like when a relative mentioned she couldn’t fly for medical reasons. Once the surveys are in, I download everything into a spreadsheet and figure out the destination, costs and logistics. I have a clear visual of what people want to do, what they can afford to do and when they can do it.

TAYLOR: It’s tempting to let the natural planner in the family run with everything, but involve others, particularly kids. Ask up front what people actually want—how much downtime, what pace they prefer, what they’re excited about. Energy levels and interests change, especially as people get older. Don’t assume you know what people want to do.

VINAY: With every client, I have a detailed intake process that’s an in-depth conversation where we discuss all the obvious questions about where they want to go and what they want to do. But then I have a few questions that are very revealing:

▶︎ What are the goals of the trip?
▶︎ What would make this vacation completely memorable?
▶︎ What would ruin this vacation for you? (People always have a lot of answers for this one!)

THE TAKEAWAY: A questionnaire gives everyone a voice and helps prevent squabbles or hurt feelings later.

ROBINSON: Early on, I’ll ask, What’s worth celebrating in your life right now? It doesn’t have to be huge. Maybe someone just graduated or started a business. Maybe a big birthday is coming up or someone had a baby. We don’t always know what’s happening in our relatives’ lives, and a multi-gen trip is the perfect moment to share it. It’s also a time to honor the past and remember the folks we’ve lost.

THE TAKEAWAY: Celebrating loved ones transforms a trip into something deeper than a vacation.

TAYLOR: The best destination has to work for everyone’s pace. You want a mix of high-energy options, like theme parks or the outdoors, balanced with calmer activities that appeal to grandparents or younger kids. For me, the Florida Keys or Orlando is a multigenerational favorite. You can do them on a shoestring or as a splurge, spend time at a theme park or at a nature preserve.

STARR: With a cruise, you have different categories of rooms, so people who want to travel on a budget may do so, and the ones who want something fancier also have options. With food and drinks already included, there’s no worrying about who’s cooking or splitting restaurant bills. And there’s plenty of flexibility. You can do an excursion together one day and go your own way the next. It’s a shared trip but with options.

THE TAKEAWAY: The best destination isn’t the flashiest—it’s the one that offers flexibility and meets everyone’s needs, from toddlers all the way up to grandparents.

MOORE: Often the big rental house looks like the smartest and best choice. Dinners under one roof are great! But when you put three or four generations together, you’re also signing up for less privacy and more noise. A baby crying at 5 a.m. or late-night cocktails in the living room can ripple through the whole house. Think carefully about how much togetherness your family really wants.

MAXWELL: Be thoughtful and considerate about divvying up bedrooms. Don’t stick late sleepers near the heart of the action like the kitchen or living room, where people will be gathering. I look for rentals with multiple levels so each family has its own floor—built-in privacy makes a huge difference.

VINAY: Sometimes a hotel or resort is the smarter choice. More often than not, they’re ADA-accessible. And hotels solve common group-travel headaches: connecting suites for families, pools and game rooms for kids, daily housekeeping and no chores to divvy up.

THE TAKEAWAY: Where you stay matters as much as the destination. Choose accommodations that provide space to be both together and apart.

MOORE: Renting a van or bus might seem like a good idea because it can save money and feels more efficient. But if you’ve got little ones in car seats, kids who need naps or just folks with different agendas, that big van removes a lot of freedom.

THE TAKEAWAY: For the most flexibility, make sure you have enough sets of wheels.

STARR: I want us all to still like one another when we finally are on vacation, so after I’ve wrangled my survey spreadsheet and figured out where we’re going and the main logistics, I hand things over to my travel specialist. At that point, I’ve done the hard work of shaping the trip, and she’s the one who turns it into a polished plan with rooms, excursions and all the little details. My family books directly through her, so I can focus on the fun part of planning without carrying the whole weight myself.

Some questions to ask when looking for a travel agent: Do they have testimonials? Sample itineraries from past clients who went to that destination? How do they handle payments? Does the money ever hit the agent’s account? This one is a huge red flag. Reputable agents use tech where the money is in holding and they can’t touch it.

VINAY: Families often try to do too much. One activity a day is plenty. People need downtime to just hang out or do their own thing. A good travel specialist can help balance the plan.

THE TAKEAWAY: Shape the big picture, then let a travel specialist handle the bookings, payments and itinerary details.

MOORE: Have the money talks (there will be more than one) right at the start, even if it’s awkward. Spell out the costs, what each person can afford, and who’s paying for what. If the grandparents offer to pay, don’t see it as them buying influence. It’s a gift, and the real payoff is time together.

ROBINSON: Give yourself a lot of time—ideally a year—to plan so relatives on tighter budgets can save. And if the first plan feels out of reach, adjust. Pick a place where everyone who wants to be there can come, regardless of finances.

THE TAKEAWAY: Be up front about money and open to adjustments—and plan early.

TAYLOR: If you’re crammed into every meal and activity, the little quirks and differences will start to grate. But when people have space to decompress, you come back together with a lightness. The goal isn’t to spend every minute as one group. It’s to make the experience good enough that everyone wants to do it again!

THE TAKEAWAY: Taking breaks from the group isn’t a sign of something wrong—it keeps the traditions alive.