Planning Your Next Multigen Trip

Ten tips from our two experts that will help make your next vacation an unequivocal success

BY ANDREW SESSA — Spring 2018

1. Get a (big) head start. “Things get complicated when you multiply family members’ schedules,” cautions Wilson Wetty. “In many cases, when setting up a trip, we have to pick dates 18 months in advance to find a time that works for everyone.”

2. Assign a point person. If you have 24 different but equal opinions, you’ll never get anywhere, says Wilson Wetty, who always tells clients to designate one or two primary people as the coordinators and decision-makers. If you have more than 20 travelers, Ezon suggests hiring anon-site coordinator for the entirety of the trip itself.

3. Give everyone a voice, too. Wilson Wetty likes to offer each family member a day or part of a day to plan, focusing on something of interest to him or her. “It’s a great way for people to get to know their relatives better and to find out what they enjoy doing,” she says.

4. Pick destinations with meaning. Ezon advises selecting locations with significance, be it cultural or historic (such as Vietnam) or environmental (such as the Galapagos). He also likes helping clients organize trips to accentuate a family’s own values and passions, such as music and theater, art, military service, philanthropy, or sportsmanship. In a similar vein, Wilson Wetty offers the idea of going to an ancestral homeland to explore your family’s heritage and genealogy.

5. Consider cutting yourself off. “Big cities often supply too many distractions for individuals to all go off their own separate ways,” warns Ezon. “More confined, remote options create better opportunities for togetherness.”

6. Go all in. “Plan immersive experiences that appeal to the whole family,” says Ezon, who has set up art classes at museums such as the Louvre in Paris and scavenger hunts through cities such as Buenos Aires. “The goal is less about education exactly and more about connection.” Wilson Wetty suggests “getting to know a culture in a different way,” finding that authentic, local interactions such
as volunteer opportunities and school visits help turn people, especially young ones, into better global citizens.

7. Do the unexpected. Ezon likes to think outside the box to pull people out of their comfort zones, finding that it “makes for memorable experiences and better bonding. Even if you have a relatively conservative group, make at least one experience ‘crazy.’ ”

8. Plan time together — and apart. “Leave pockets of downtime for organic interactions when everyone is together and connections truly happen,” advises Ezon. “Set out board games and cards, and schedule leisure time in a contained area.” But, at the same time, he says, “don’t feel obliged to keep everyone together all the time. Plan options for people to split up, making some activities optional.”

9. Have fun with it. Ezon likes to orchestrate team games. “Whether it’s a sport like football or a Family Feud game-show night, a cooking contest based on Chopped, or family Olympics, these experiences always become trip highlights and bring people together like never before.” He has even repurposed corporate team-building exercises such as raft building or obstacle-course relays.

10. Make and capture lasting memories. Ezon has brought in photo and film crews during multigenerational trips to create family documentaries, or just to record the goings-on. By journey’s end, video and images from the professionals and from travelers’ own cameras and smartphones can be edited together into a final movie or montage to screen on the last night — and then to keep forever as a perfect souvenir. 

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Our two travel insiders tell you where you’ll want to go on your next getaway


both top Virtuoso
travel advisers

Jack Ezon and his team at Ovation Vacations book nearly 200 multigen trips a year.

At Valerie Wilson Travel, Kimberly Wilson Wetty and her team also book hundreds of these trips each year.


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