Tips to Create a Harmonious Multigenerational Trip

A guide to planning a family adventure that makes everyone happy — kids, parents and grandparents

For multigenerational vacations, select a location that offers flexibility and meets everyone’s needs, from toddlers to grandparents.

Ryan Snook

Rachel Walker,

AARP

Published November 24, 2025

Cotrillia Ewing knows it’s time for a big vacation when she gets an online survey. Not from a travel agent or some hotel or airline rewards program. The extensive and detailed query comes from her daughter, Brandi Starr. It goes out to Ewing, 72, and as many as 30 others as plans get laid for their next great extended-family adventure.

“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, text or, for 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, and what are their 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 their 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 potential minefields and leave everyone in your family eager to embark on their next great vacation.

The experts

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 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

Getting started: Don’t assume anything

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.

Make the trip a milestone

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 multigen 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.

Pick the place that fits, not just wows

a family sitting on the back of a boat in the middle of the ocean

Rob Taylor and his family in Key West, Florida. The day spent on a chartered boat was the favorite part of the trip.

Courtesy Rob Taylor/2TravelDads

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.

an illustration of people sitting at a table while eating and talking

Choose accommodations that provide space to be both together and apart.

Ryan Snook

Beds, space and sanity: Get the right accommodations

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.

a family posing for a selfie while wearing biking helmets in a wooded area

(From left) Kirsten Maxwell’s son Ronan, nephew Landon, sister Kori, Kori’s husband, Michael, and niece Kiera. Maxwell’s family traveled to Lake Tahoe, California.

Courtesy Kirsten Maxwell

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.

Shared adventures, but separate cars

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.

Pass the baton: Let a pro work the details

a family poses for a photo with the ocean in the background

Brandi Starr (right) and her family took a cruise in the Caribbean.

Courtesy Brandi Starr

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.

The price of harmony: Talk budgets before you travel

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.

Allow for alone time: Breaks build bonds

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.

Travel tales

Kirsten Maxwell, age 52

Founder of Kids Are a Trip 

We went to Lake Tahoe in California. Our group included my husband, our three kids, my sister and her husband, their two kids and our parents.

What was your favorite part of the trip?

Every morning we would go on walks together, and in the evening we hung out and had dinner on the patio. We could just be together and talk about our lives.

What was particularly challenging?

Cleaning up. Everyone’s version of cleanliness was different, and we had two 20-year-olds and older teens. My mom and dad were telling the kids to pick up after themselves. I tried to encourage everyone to be more mindful, but there were a lot of eye rolls — on all sides!

What’s the one activity that everyone agreed on?

We went rafting down the Truckee River. We divided up, so the kids were in one raft and the adults had another. We were racing and splashing and chasing one another. It was a blast.

What’s the one meal that became emblematic of the trip?

The kids found a Mexican restaurant called Las Panchitas that we all fell in love with. We went there three times. It was such good food.

Brandi Starr, 47

Multigenerational vacation planner

I recently took my mom, 72, my 10-year-old son and my mom’s best friend on a seven-day cruise in the Caribbean.

What was your favorite part of the trip?

When we were on Grand Cayman, we decided to rent a Jeep instead of doing the cruise ship excursion. Nothing specific happened, but before the trip, my mother had surgery. To have come out on the other side of that and be on our own, being silly and laughing, added up to something really meaningful.

What was particularly challenging?

Navigating my mom’s wheelchair was more challenging than I expected. We went to a bee sanctuary not knowing that the whole path was made of rocks, and my mom couldn’t do the tour.

What’s the one activity that everyone agreed on?

In Mexico, we went to Pueblo del Maíz in Cozumel and learned about the Maya culture. We watched a traditional Mayan dance, learned about the cacao bean and chocolate, and made tortillas. There were aspects of the tour that spoke to each of us.

Rob Taylor, 43

Founder of 2TravelDads

My husband Chris’ parents flew to Florida to visit us, and then the six of us — Chris, his parents, our two kids and I — went to Key West. We rented side-by-side condos at the Coconut Beach Resort.

What was your favorite part of the trip?

The beach access was incredible, but it was being out on the water with all of us together that was my favorite. We spent one day on a chartered boat. It’s actually cheaper to charter a boat for a group our size than to do a commercial tour, and everyone was happy. The kids snorkeled and swam. Grandma sat in the shade on the boat and visited with everyone. Grandpa fished. Chris and I were elated to be in a beautiful place with the people we love.

What was particularly challenging?

My immediate family is acclimated to the Florida heat and humidity, but my in-laws were not. Seeing them crash because of the intense weather was tough.

What’s the one activity that everyone agreed on instantly?

We all loved the boat charter. It had everything: shade, fun, sightseeing, wildlife, fishing, swimming.

What’s the one meal that became emblematic of the trip?

Even though fried fish and key lime pie are the food you’ll find in the Keys — and I love them — grilling out on our vacation rental patio was my favorite meal. Just being together and preparing simple, delicious food was the best.