Tips for Planning Multigenerational Family Vacations

Since she began selling travel in 2010, travel advisor Laurel Perry has planned dozens of multigenerational family vacations. “I like the puzzle of it. It’s fun to put it together,” said Perry, senior travel advisor for Ciao Bambino.

As demand for multigenerational vacations surges travel advisors new to planning such complex vacations might find the task of putting together all the puzzle pieces overwhelming. We asked Perry and other travel advisors to share their advice.

Four fundamentals
The advisors we spoke with shared four critical tips for planning multigenerational vacations:

• Do an in-depth consultation at the outset to gather information about all participants and the trip they envision.
• Establish a single contact person for subsequent communications.
• Navigate family dynamics with great care.
• Design a trip to satisfy all participants, accommodating diverse ages, needs, wants, tastes and priorities.

Pleasing everyone
Trying to please a group of travelers of varied ages, interests, tastes, and abilities is one of the most important and daunting tasks when planning multigenerational vacations, advisors said.

“Definitely the most challenging [aspect] is making sure everyone is satisfied and that you find a vacation that suits everyone’s needs and wants,” said Ilisa Oman of One World Family Travel in New Market, MD.

“It’s hard to do. It’s the diversity of interests. And with different age groups comes different activity levels. What’s good for the grandparents isn’t necessarily good for the toddlers. Or you might have teens who want to be more active and others who want to sit on the beach. It’s balancing everything to keep everyone happy,” Oman said.

Oman’s advice? “Be patient. Qualify your clients. Try to talk to everyone in the group to find out exactly what everyone likes and dislikes. Don’t just find out what they want to do. Find out what they don’t want to do. Ask lots of questions.”

Dive deep early
Catherine Parkin, an independent affiliate of Brownell Travel, emphasized the importance of “extensive discovery calls at the beginning of the process, even if you know the lead client.”

“Try to anticipate all of the things you will need to know, not only as it pertains to their trip interests but the operational needs of the trip,” advised Parkin who is Littleton, CO.

Parkin urged advisors to pin down certain details right away, including confirming that trip dates work for all parties, determining who will pay for the trip, identifying a primary contact, and setting up a survey or call with all travelers to establish interests and needs.

She also commented on the challenges of designing a trip that satisfies competing needs and interests, noting that “a place that is fun and functional for toddlers, children and teens may not meet the luxury requirements of grandma and grandpa.” 

“Additionally, the person funding the adventure may not be in tune with everyone’s needs,” Parkin warned.

Identify trip’s purpose
Nicole Sicard of Paradise Haven Travels begins her conversations by asking about the why of the trip – “what’s the purpose of the trip, what’s important to you, why is the family coming together, is it a celebration or just wanting to come together as a family.”

The why is important, Sicard explained, “because while I’m doing the consultation I’m already thinking of places, and I’m starting to formulate what special things could be done during their time there.

“I don’t just want to book their travel. I want to implement something special, whether it’s a special tour, a special dinner. I need to know the why to figure out what the special component of this trip is going to be,” Sicard said.

Important practicalities
Perry of Ciao Bambino recommended nailing down three practicalities at the outset because they will determine much of what follows:

• Do the grandparents have mobility issues?
• How old are the children?
• What room configurations does the client want? Will children be sharing rooms with their parents? Will cousins be grouped together?

Be sure to take into consideration individuals’ special needs when planning the itinerary, said Perry, who’s based in Clearwater, FL.

Mobility issues can impact lodging choices and tour activities, and it’s important to know the ages of the children so the trip includes age-appropriate destinations and activities, Perry said, adding, “Your goal is to make everybody happy; what makes the grownups happy is when the kids are happy.”

Perry, who specializes in multi-destination family trips to Europe, offered a few examples. If you’re planning a wine tour excursion, choose a vineyard where there are farm animals that the kids can go see while the parents are drinking wine. Or if your group is visiting Lucca, Italy, make plans for the grandparents to enjoy a café while younger members head off to climb Torre Guinigi.

Using Zoom, maintaining boundaries
Advisors recommended connecting with all family members early in the planning process, and many favor Zoom video calls for this purpose.

“I may do a Zoom call with everybody in the beginning so I can get to know what everyone’s like, what the kids are like, what their interests are,” said Perry, who likes to include children and youth on the hour-long Zoom calls.

As important as it is to involve everyone early on, it’s just as important to establish one contact person and decision-maker going forward, so you don’t end up overwhelmed when multiple people email you with their individual preferences.

“You definitely have to rein them in. You have to boundaries, or they’ll run you ragged,” Perry warned.

Parkin, the Brownell affiliate, noted that designing a vacation that satisfies everyone’s needs and wants while maintaining control over the planning process requires some finesse. “There is a delicate balance of not having too many cooks in the kitchen and still setting everyone up for a memorable vacation.”

Managing family dynamics
Another aspect of planning multigenerational vacations that requires finesse is dealing with family dynamics. “Not everybody wants to do the same thing, and I often am the arbiter of those discussions,” said Wendy Chambers of Victory Travel in Westport, CT. “You end up playing coach, moderator, and therapist in some of these multigenerational trips.”

Sicard cautioned against taking sides when family members disagree. Stay focused instead on listening to what each person wants. “If it gets to the point where they cannot agree, I put it back on them, and say, ‘These are my suggestions, however, I think you as a family need to come together and figure this out. I’m not going to decide.’”

It helps to have confidence in your professional knowledge and expertise, she said. “It goes back to you knowing the product, knowing the locations, and then giving them advice in a professional way on how to pull all of this together.”

Money matters
Establishing a budget to guide advisors’ trip recommendations will be relatively simple when one or two people, typically the grandparents, is footing the entire bill, as often happens on multigenerational vacations.

But when each family unit is paying its own way the task becomes more complex. “You are at the mercy of the lowest budget if this person has $1,000 a day, but this person has $500 a day,” Perry said. “That’s the kind of thing I have to get to first – are they paying separately?”

When individual families are paying separately, it can be challenging to get everyone on the same page budget-wise, Oman said. “They need to come up with a set budget. I tell them the family has to have that conversation with one another.”

The last word: Value your time
Planning multigenerational vacations often involves more than the usual amount of client communication as family members sift through the options in between consultations. “Most of our work is not when we’re booking. The hardest part is that consultation, that research and going back and forth,” Sicard noted.

It can get very time-consuming. Sicard’s advice to her travel advisor peers? Set your consultation fee accordingly.