How to Plan and Enjoy a Multi-Generational Vacation

Tell grandma, the aunts and uncles to start packing: Multi-gen travel is becoming more popular, and for good reason.

Multi-generational, or multi-gen, travel is catching on quickly in the U.S. This year, a little more than one in every three American families will take a multi-gen trip, according to AAA research.

These trips are loosely defined as three or more generations coming together—often kids, parents and grandparents from different parts of the country or the world—to explore a new destination or revisit a favorite location.

If the thought of organizing your extended family’s next multi-gen experience makes you reach for the antacid tablets, though, hold on.

Plan, Plan, Plan

Planning is the name of the game when it comes to getting a lot of people together for a harmonious adventure.

Jack Ezon, the president of travel agency Ovation Vacations, plans large-scale events and multi-gen trips for groups of 10 to 30 people. He said he likes to start planning complex multi-gen trips at least a year in advance.

“When you have more time, you have a lot more options for venue space, the hotels you want to be in, getting connecting rooms and things like that," said Ezon. 

According to Ezon, one of the biggest challenges to planning large, multi-gen vacations is trying to make everyone happy. The most important skill, he said, is listening.

“Finding compromise when dealing with multi-gen is the key to success,” said Ezon. “Our first thing is listening to the person overseeing it … not just to hear but to listen to what they’re saying. Sometimes what people are saying isn’t what they mean or there’s more to them.”

As you plan, whether you're doing it yourself or working with an agent, define expectations about the destination and experience, as those affect your budget.

“If you only have $10,000, you’re not taking your family to Africa for two weeks,” said Ezon.

Roy Ramsey, the director of operations at Betty Maclean Travel, said that clients sometimes come to the agents with “champagne expectations on a beer budget,” but he stressed importance of keeping expectations in check.

“One of our agents has a safari booked that’s $300,000 for 12 people,” said Ramsey. “Another has a group of 19 and the cost of just their cruise alone is $245,000.”

Sasakwa Lodge in Tanzania, a popular destination for multi-generation luxury travel

Ramsey said a rule for luxury, multi-gen travel budgeting is to expect to spend approximately $1,000 per person, per day.

Whether or not your budget is that grand, everyone will want to have a say in how the money gets spent. The experts say having few key decision makers can make or break a multi-gen experience.

“The ones that have the most success are the ones that have a matriarch or patriarch who makes the decisions and doesn’t allow other travelers to change the parameters,” said Ramsey.

Ezon said his team listens to several members of the family to try to understand their wants and desires but ultimately has only one decision maker for the group. Although it sounds counter-intuitive, Ezon also recommended not stressing out too much about the details within the vacation and to keep in mind that the family is together to have fun.

“We like to remind people that they’re going to be together but they don’t need to be together 24-7,” said Ezon. “Sometimes it’s better for them not to be together all the time.”

Organizing activities for all ages—this is a family vacation, after all, for everyone from the kids to the parents and grandparents—can make bonding easier and make the experience feel more genuine. Sometimes it's best to plan experiences for smaller groups within the larger collection of travelers.

“An example would be a scavenger hunt or an amazing race through the city,” said Ezon. “We did it recently in Buenos Aires. There were ages four to 80. They biked, went in cars and some went on Vespas. There was a competitive edge but they also bonded with their small groups before coming together for an amazing lunch and tango session. It didn’t bore the kids and wasn’t too exhausting for the adults.”

Get There: Flights and Accommodations for Multi-Gen Groups

Once the destination and budget planning is done, it’s time to think about getting there and where you’ll stay.

Flying—and making flights for everyone from different airports—can be a hassle.

"You have to think about access," said Ezon. "If you've got four to five small children coming, you don't want to have to take three connecting flights to reach the destination."

Travel companies can sometimes create a meeting contract for multi-generation groups in which travelers are departing from different airports. The meeting contract is an exclusive contract the group has with one airline. Ezon said that using this tactic can sometimes yield flight discounts for families.

Lodging and accommodations for multi-generational adventures are also a large part of the success or failure of such trips.

“Private shared spaces are very important for multi-gens,” said Ezon.

Villas, bungalows and other lodgings that have a shared common space and kitchen are some of the most popular accommodations for multi-generational adventures. As multi-generational travel grows, new players in the hotel and resort industry have risen to try to meet the challenge of facilitating lodging worthy of luxury, multi-gen travel.

Encore Club, Orlando, vacation rental

Orlando's Encore Club, which opened in April 2016, is one example. The club has more than 700 individual homes for rent with five to 13 bedrooms in each home.

“The niche we’re playing at here is multi-generational travelers,” said Nick Falcone, the manager of Encore Club. “Think four-star hotels but staying in houses. It’s similar to a gated community with a clubhouse, ball fields, a water park and other amenities.”

“There’s multi-generational travel that we hadn’t seen 20 years ago,” said Art Falcone, Nick's father and owner of Encore Club. “I’m a baby boomer. We’d go away with our parents as young kids. Today my parents are still alive so there’s me, my kids, their kids, my parents, plus family friends that want to travel together. That’s a major shift in travel.”

Art estimated that a family in need of 10 to 12 rooms could rent a house with Encore Club for $550 per night. He estimated that the average cost at that rate would come between $30 and $40 per person, per night.

While traveling in a pack, if renting a home near a resort or theme park is out of the question, hotels and condos near outdoor recreation areas like national parks are another popular destination that the whole family can enjoy.

Hotel Terra Jackson Hole, Wyoming

Jackson Hole, Wyoming, is an example. The quaint town is near many national parks—Grand Teton National Park surrounds the hotel and Yellowstone is less than a two-hour drive—where a vast age range of family members can explore. Tyler Barker, general manager for Hotel Terra Jackson Hole, said Jackson Hole is popular because of a history of ranches geared toward multi-gen travel.

“[Multi-gen] travel has been typical of Jackson Hole starting with dude ranches where families come and spend time with each other," said Barker. "Both Teton Hotel Lodge and Hotel Terra Jackson Hole lend themselves to multi-gen travel because all our units have lock-off capabilities. That means we can create one-, two- and three-bedroom layouts.”

Barker said that each unit also has a kitchen and dining area, which keep the family together.

Naysayers of multi-gen travel will quote high costs, stress in transit and other factors that deter travelers from attempting the adventure. So why would anyone want to make travel with their extended family a priority?

“People want to disconnect to connect,” said Ezon. “They want to bond with their family and get to know them. We’re so bombarded with data and distraction that we rarely look at what we have.”

Jamie Jackson
About the author

Executive Digital Editor for WhereTraveler

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