Take a One-Big-Happy-Family Vacation!

BOB CARSWELL'S FAVORITE MEMORY of his mom, Lois, is the sight of her wading into a river in Belize so that she could visit a burial ground on the other side. "The river kept getting deeper," Carswell says, "and my mother was five foot one, in heels." When the water was over her head, the undaunted Lois simply wrapped her arms around the neck of the tour guide, who ferried her the rest of the way.

Lois Carswell passed away in 2014, but the story of her traversing that river in Belize is one her children and grandchildren will tell for decades to come—just as they will carry on Lois’ tradition of keeping their bicoastal family connected through travel.

"Everybody has their own lives, and we're all so busy. That's why spending time together on a trip is great. In a way, it doesn't really matter where you're going."
—Bob Carswell

In a tradition she started with her husband, Donald, over the years, Lois had taken her extended family—her three adult children, their spouses, and her four grandchildren (then ages 10 to 21)—to such diverse locales as Tanzania, the Galapagos Islands, Costa Rica and Tuscany. Her adventurous spirit always made their vacations memorable. But, above all, it was the quality time this far-flung family(pictured above) spent together each year that they came to value most.

"Family was so important to my mom," says Carswell. "Everybody has their own lives, and we're all so busy. That's why spending time together on a trip is great. In a way, it doesn't really matter where you're going."

The Carswells' vacation of choice is one that many families everywhere are discovering. In 2014, the travel-marketing firm MMGY Global reported that multi-generational vacations represented half of all vacations taken by both grandparents and parents. These run the gamut from camping in a national park to touring China. In fact, on a quarter of vacations taken by American travelers, all three generations—grandparents, parents and kids—were together.

The logistics of planning a trip for so many people can seem daunting. "It's important to be honest with yourself," says Eileen Ogintz, creator of the website Taking the Kids (takingthekids.com) and author of The Kid's Guide series that includes guidebooks for Boston, Chicago, Los Angeles, New York and Washington D.C. "After all, you can't return a vacation." Here are three key questions you'll want to ask yourself—and the whole gang—as you make your travel plans.

Where are we going and what will we do?

"Be sure your plans are appropriate for everyone who's coming along," advises Kyle McCarthy, editor of Family Travel Forum (myfamilytravels.com). She recalls a friend with young children whose in-laws invited her family on an Alaskan cruise. The ship was small and had few activities for kids. But the big concern for the young mother was the deck, where the railings were widely spaced. "The whole time, she felt like she had to watch over her kids so that they didn't fall into the water." Needless to say, the trip was hardly restful or pleasant.

As you work with your family to outline your trip, respect everyone's needs and tastes, and in cases where there are differing opinions, try to reach compromises. Consider coming up with several trip options. Then solicit input from everyone coming along—including the kids, suggests McCarthy.

The Carswell family cooks up trip plans at their annual summer get-together. "Everybody throws an idea into the hopper, the family discusses it and then we decide where we want to go. My mom would start planning trips two years in advance to accommodate school and work schedules," recalls Bob Carswell—a practice he plans to continue with his siblings.

To find destinations that might appeal to family members of all ages, consider all-inclusive resorts and cruises. These options offer a variety of activities and dining choices—and often child care—at a fixed price. And if you prefer a less structured vacation, look for ways to incorporate activities for all ages. Ask friends for suggestions, or consult a travel agent who specializes in multigenerational family vacations.

Who's paying for what?

Are you paying for travel and lodging? Should individual families be responsible for their own airfare? Who pays for meals? Lift tickets? Theme park passes? "A lack of clarity about these details can undermine the sense of family unity a multigenerational trip is intended to create," says Stacy Allred, Managing Director and Head of Merrill Lynch Wealth Management Center for Family Wealth. "If your entourage is sizable, it's essential to budget carefully in advance and determine financial responsibilities up front."

Allred recommends sending each adult a detailed email spelling out the costs each family member will cover. "If your son assumes from your invitation that you'll pay for everything, and he ends up picking up the tab for half the meals, that could quickly become a source of tension," she explains.

How will we all get along?

Every family has its own set of dynamics. If there are tensions between family members, they won't necessarily go away just because you're in a relaxing location. To prevent—or at least minimize—friction, you should all agree to certain ground rules in advance, says Ogintz. One cardinal rule: "Don't discipline another person's child. Leave that to the parents." And don't feel the need to spend every minute together as a group. "Everybody doesn't have to be in lockstep all the time."

If you plan your multigenerational trip carefully, you may see it work a kind of magic on your family. In 1984, the Carswells took their first overseas family vacation, to Scotland. Lois’ two sons and daughter were then in their college years and shared uneasy, competitive relationships. But after two weeks of golf, exploring castles and getting lost in the Highlands, "we suddenly decided we liked each other," recalls Bob Carswell.

"We told our mom, 'We'd rather have the trips than have you save the money and give it to us later.' Now more than ever, we treasure the memories we made together."

If you plan your multigenerational trip thoughtfully, you may just see the birth of a similar kind of new tradition in your family.