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3 Generations, 1 Great Vacation

Traveling with family can bring you all closer together. Use these questions to help you plan a memorable getaway without breaking the bank.

ONE FATHER PUTS IT THIS WAY: “My two favorite things are being with my kids and grandkids, and traveling. So I’m always looking for chances to do both at the same time, and I’ve found that some of the most fulfilling moments of my life have been on those family trips.”

These days, vacation time is becoming even more important to maintaining close family ties. Grown children move away for work, kids get locked into busy schedules, grandparents develop active lives in retirement, and suddenly, it’s all too easy to feel you’re losing touch. That’s why more and more families choose to make special occasions out of their moments together—by organizing vacations that allow them to reconnect as a family.

“One of the reasons multigenerational travel has continued to grow in popularity is that it gives families a chance to do so many important things together—to learn about new places, to share values and wisdom, to recharge,” says Matthew Upchurch, chairman and CEO of Virtuoso, a leading global network of luxury travel agencies. He adds, “Many families also find that when they’re outside their everyday environments and having interesting experiences together, they’re often more open to each other. Conversations happen on the beach, or at the dinner table at the end of an exciting day, that just don’t happen at home.”

5 Tips for Family Trips. Photo of vacation item checklist.
Take Everyone’s Wishes into Account. Respect people’s needs and tastes. Try to reach compromises. Consider several trip options. Photo of hikers reading a sign post on a walking trail.
Consider All-inclusive Resorts or Cruises That… Appeal to all ages. Have a variety of activities and dining choices. Often offer child care. Aerial photo of beach full of people.
Be Clear About Money. Budget carefully in advance. Determine fiscal responsibilities up front. Photo of credit card, receipt and pen on a dining table.
Agree to Certain Ground Rules Ahead of Time. Don’t discipline another person’s child. Schedule time away from the group. Photo of family playing games in a living room, and talking in a kitchen.
The Priority: Enjoy Yourselves. Photo of family holding hands and jumping in a lake.

Those experiences can run the gamut from camping in a national park to touring Europe. No matter what the destination, traveling with a multigenerational group is an exercise in logistics—and economics. As you plan your next big family trip, here are four questions that can help give you and the people you love the most rewarding experience at the most reasonable cost.

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 ( 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, she suggests.

"Renting a home—or multiple homes, if you’re traveling to several locations—can make things easy in terms of managing the costs of lodging."

—Merrill Financial Advisor Patrick Dwyer

Options like all-inclusive resorts and cruises offer a variety of activities and dining choices—and often child care—at a fixed price. If you prefer a less structured vacation, look for ways to incorporate activities for all ages. Ask friends for suggestions, or consult a travel advisor who specializes in multigenerational family vacations.

How can I manage costs?

The first rule of keeping travel costs in line is to set a budget based on what you can realistically expect to pay for the places you want to go. As anyone who travels knows, the price range for a single destination can vary widely based on how you want to travel. Upchurch notes that popular family destinations such as Orlando can run approximately $100 per person per day for a seven-day vacation at select Disney All-Start Resorts, rising to $1,000 per day (depending on the size of your group) for a VIP experience led by a private guide. Similarly, for a South African safari, you can expect to pay, after airfare, from around $300 per person per day for a three-star safari lodge to $1,200 per person per day for a five-star experience.

In setting a budget for your trip, try to keep extras to a minimum, suggests Patrick Dwyer, a Merrill financial advisor who speaks to many of his clients about their travel plans. “Your first order of business is to determine what’s important for you to do, and the second is to cut down on the things that are less important.” He adds, “If you don’t want to tack on too many extras, cruises can be the simplest thing for a large group to do and, generally speaking, they tend to please a wide variety of people.” Another tip for keeping costs down is to look for alternatives to hotels. “Renting a home—or multiple homes, if you’re traveling to several locations—can make things easy in terms of managing the cost of lodging,” he says.

"Should individual families be responsible for their own airfare? Who pays for meals? Theme park passes? A lack of clarity about these details can undermine the sense of family unity."

—Stacy Allred,
head of the Merrill Center for Family Wealth™

Who's paying for what?

Are you responsible for all of the 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 that a multigenerational trip is intended to create,” says Stacy Allred, managing director and head of the Merrill Center for Family Wealth™. “If your entourage is sizable, it’s essential to determine financial responsibilities up front.” Allred recommends sending each adult a detailed email spelling out the costs each family member will cover.

How will we all get along?

Every family has its own 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 Eileen Ogintz, creator of the website Taking the Kids ( and author of The Kid’s Guide, a travel guidebook series that includes Boston, Chicago, New York and Maine. One of her cardinal rules: “Don’t discipline another person’s child. Leave that to the parents.” And, she adds, don’t feel the need to spend every minute together as a group. “Everybody doesn’t have to be in lockstep all the time.”

Remember that the recipe for the perfect multigenerational vacation is entirely dependent on your family’s taste for adventure, financial wherewithal and collective personality. And keep in mind that where you travel is often less important than the fact that you’re doing it together. As Upchurch says, “More and more, studies tell us that people are placing greater value on two things: time with family and experiences over material things. Multigenerational travel is really a combination of both.”

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