The Fantastic Life

Multigenerational Family Vacations


One of my strengths (and curses) is that I’m forward thinking.  I spend a ton of time looking into the future, creating goals and planning the directions I want to head.  Today, I am not at the stage in my life of multi-generational family vacations BUT I am thinking about them.  

Below is a wonderful article about some do’s and don’ts when you travel with different generations. I have highlighted some I found insightful.  And, I have highlighted in green some of the locations that might just work for me.  If any reader has done this kind of travel, I would love to get some feedback/tips. 
Travel really could be the global guide for your grandchild.

Rule #3 from my book The Fantastic Life: Build Your Resumes Every Year
If you’re familiar with The Fantastic Life and LIFEies, you know that I try to work on five different resumes each year. I am constantly updating these resumes. One of the most important to me is my father resume. I love traveling with my kids, and think those family trips are the best way to add in quality time with my kids. Who knows? Maybe someday I’ll have a grandfather resume as well.


The Multigenerational Family Vacation

More Americans are including children, grandparents and cousins on trips. In an age of special diets and gadget addictions, how to make sure your adventure isn’t a road to ruin


Updated Nov. 8, 2014 8:35 p.m. ET

WHEN KATHLEEN DOYLE is on the road, she tends to seek out museum shows, opera performances and acclaimed restaurants. But during a three-week journey to Asia this year, she engaged in some far less refined activities—including zipping down the Great Wall of China on a toboggan.


“Trust me, I would not have done that on my own,” said Ms. Doyle, chairman and CEO of the auction house Doyle New York. But she was traveling with her daughter, son-in-law and their three sons, ages 10, 12 and 13—and that meant a very different kind of experience.

While some of us board airplanes and rent cars to escape relatives, many travelers are now vacationing with their extended families. For years, surveys have shown that “multigenerational travel” (trips involving at least three generations) is on the rise. According to a summer 2014 AAA poll, 36% of American families planned to take such a trip by mid-2015, up 4% from the year before. In its 2014 Luxe Report, Virtuoso, a network of high-end travel agencies, named multigenerational travel the biggest trend—for the fourth year in a row.

The biggest driver of all this togetherness, experts say: baby boomers with money and a hankering for meaningful experiences. “I think you’re seeing a desire to make moments count,” said Jason Guggenheim, the Boston Consulting Group’s global leader for lodging and leisure. “Travel is often a way to do that.” Others see the boomers as more intrepid and able-bodied than their predecessors. “They tend to be more fit and active than, say, my grandparents,” said Carol Austin, co-founder of Montana-based travel outfitter Austin Adventures.

Group holidays are more accessible than ever. “You’ve seen real travel costs go down over generations,” Mr. Guggenheim pointed out. Thirty years ago, renting a villa in Tuscany involved wire transfers, expensive international phone calls and a heap of trust that you weren’t booking a rotted-out barn. Today you can browse reviews on your phone, share them with cousins and pay via credit card.

All of which is great—if your family has no sibling rivalries, religious differences, out-of-control children or overanxious grandparents. For the rest of us, planning a multigenerational vacation might seem like a direct route to voluntary commitment—or, at least, a screaming match with in-laws.

But travel experts (and real people) say you can do it without losing your mind. And you don’t need to be relegated to routine Caribbean cruises or mouse-riddled theme parks. The multi-gen crowd is embarking on more adventurous, culturally inclined escapes—like touring Europe or going on safari in Africa.

“In the past, often you’d go to a big resort and…the grandparents would watch the kids play in the water,” said Melissa Biggs Bradley, founder and CEO of upscale travel company Indagare, which organized Ms. Doyle’s China trip. “In the last couple of years we’ve seen almost 90% of multigenerational trips have an emphasis on, ‘I’m going to be the global guide for my grandchild.’ ”

Here’s how to keep everyone happy and stay sane yourself.

Take Charge (Mostly)

Sometimes, it’s important to solicit lots of ideas and build total consensus on plans.

This is not one of those times.

“One family really wants to go on a boat, another really wants to go on a hiking trip,” Ms. Biggs Bradley said. “You end up having sibling squabbling and parents who feel like they are back to having teenagers again.”

Come up with two or three options—taking into consideration everyone’s ages, interests and limitations—and put them up for a vote. Or, if you’re paying, just set the agenda and ask who wants to come.

But, as Kim Gorsuch learned from a trip to Buenos Aires several years ago, make sure you’re not too in charge.

Ms. Gorsuch, the Austin, Texas-based founder of Weeva, which lets users compile stories and photos from different sources into books, was staying at a hotel with her husband, two children and parents, who were happy to let her lead the way. One afternoon, the family took two separate taxis to a tango spot—which Ms. Gorsuch and her husband were unable to find. Her parents didn’t know the hotel’s name or address. Nobody had cellphone service.

Ms. Gorsuch’s parents found their way back—three hours later. It makes things simpler to have one decision maker, but ensure everyone else is clued in.

Plan Ahead. Way Ahead.

It can be hard to herd all your relatives together for a trip. “You’re dealing with three generations of calendars,” said Ms. Biggs Bradley. “There are school schedules, commitments in the summertime. How do you find those two weeks when someone doesn’t have a lacrosse tournament?”

Most families can go away over the winter holidays and in early June, after school ends and before summer programs begin. But those times also tend to be very busy for travel destinations—and in the case of a multigenerational escape, you’ll be looking for swaths of free rooms or entire villas. Everyone will also need to book transportation. So start planning a year or more in advance, if you can.

Pick Your Happy Place

It’s a big world—and there are a lot of factors to take into account when settling on where to take your family.

“You really have to look at how people are going to get there,” said Lucretia Marmon, a retired journalist who has organized several trips for her extended clan, which now includes babies and the over-75 set, and is scattered around the globe. One of her most successful trips involved renting a beach house a few hours from her own home outside Washington, D.C. “They could all come [to D.C.] and just load into cars,” she said.

Also consider the type of destination, keeping in mind what everyone likes (or is able) to do. Grandparents don’t necessarily want to watch the kids while the rest of the group goes skiing. Small children can only tolerate museums for so long.

“You want a place where young kids can be really active but older people can be really comfortable,” said Ms. Biggs Bradley.

Though often maligned, cruises offer an abundance of activities and dining options, let families be on the move without having to pack and unpack, and often have child care. They don’t have to have humdrum itineraries, either—trips to the Galápagos Islands and Turkey can easily include boats, said Ms. Biggs Bradley.

Ms. Austin, of Austin Adventures, suggests Costa Rica as an international destination; it’s in the same time zone as Chicago, and has excellent beaches and tons of wildlife-viewing opportunities. Rent a villa in the Italian countryside or south of France and you can combine fantastic food, charming towns, cultural excursions and outdoor activities.

Make Accommodations

When looking at lodging options, two important considerations are budget and family must-haves.

“If a daily spa treatment is of key importance, a villa is not going to be the right solution,” said George Morgan-Grenville, CEO of bespoke travel agency Red Savannah. “If you need a fully equipped gym, a hotel is probably going to be the answer.”

For Ms. Doyle’s trip to China, for instance, it was imperative that every hotel have a pool. “We knew it was going to be hot, we knew we were going to be jet-lagged,” she said. “We needed breaks in the day without just having the kids on their iPads.”

Some might shy away from villas—or, in less fancy terms, vacation rentals—because they can seem expensive. But a $20,000-a-week property might end up being a comparative bargain if it can sleep 15; that comes out to roughly $200 a night per person. Other advantages include privacy and the possibility of dedicated staff.
Arranging a happy house isn’t just about counting heads and beds, however. If relatives have trouble navigating stairs, you’ll want to look at single-story properties. When several parties are sharing costs, it helps to have what Red Savannah calls “multiple democratic bedrooms”—quarters of comparable size and quality, so nobody feels shortchanged.

“We look for places that have large dining areas,” Mr. Morgan-Grenville said. Some houses can sleep, but not seat, a dozen guests. “And what’s really important is lots of hidden spaces—places where you can go and read a book after lunch or play Scrabble.”

Nothing screams “conflict potential” like trying to choose a restaurant that will make 12 people happy—or settling on who’s going to cook and clean up. And, chances are that at least one member of your group has dietary restrictions. By some estimates, about 5% of the population is vegetarian. According to market research firm the NPD Group, in 2013 nearly a third of Americans said they were trying to avoid gluten. And then there are the plain old picky eaters.

Larger resorts and cruise ships tend to offer many dining options; if that’s still a challenge, gather for just one meal a day.

Years of planning getaways taught Ms. Marmon to assign cooking teams for each night of the trip. “Put the non-cooks with people who can cook,” she said. “Everyone had to cook twice. ”

Or, you can make meals someone else’s problem. Many high-end rentals come with chefs; if yours doesn’t, you can hire one to handle planning, shopping, cooking and cleaning. Sound extravagant? Mr. Morgan-Grenville rented a villa for his family that included a chef, and estimates that it came out to about $25 a person per day.

Get Creative with Kids
The first time Ms. Doyle took her children to Paris, they went to the Louvre. Cue the groans. Don’t worry, she told them—they’d only visit one painting. “Of course, to get to the ‘Mona Lisa’ you have to go through about 100 rooms,” Ms. Doyle chuckled.
Traveling with a gaggle of children has its upsides—they have plenty of playmates, and older kids can (theoretically) help with younger ones. But given the potential for drama, it pays to discuss expectations in advance, and to be creative about avoiding problems.

Before their China trip, Ms. Doyle’s son-in-law drew up a contract for his sons. One clause: “I am a New Yorker and New Yorkers walk. I will walk whenever it is required.” Another promised that there would be fun every day—but not every moment of the day.

Ms. Marmon thought quickly when she arrived at a beach rental filled with objects that the children were liable to break. “I took a picture of each room, then I picked up every piece of pottery and art and put it in the office and closed the door,” she said.
The last day, she put everything back. The property ended up being an ideal fit for her family. “I want that house again!” she said.


THE HITCH: Tech-addicted kids
The Fix: Look for a location that offers tons of hard-to-resist activities—kayaking, horseback riding, arts and crafts. At the start of the trip, establish gadget-free zones and times.

THE HITCH: Special diets
The Fix: Rent a house with a chef who will plan menus, shop and cook. Or, choose a cruise or resort with a number of dining options.

THE HITCH: Loud sleepers
The Fix: Seek out a property with a separate space—like a guest cottage—for outliers like snorers, newlyweds or parents whose infants are up all night.

Skip to content