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3 Generations, 1 Great Vacation

Big family trips might be on hold for now, but nothing's stopping you from planning a vacation that can bring you all closer together. Use these questions to help you create a memorable getaway without breaking the bank

3 Generations, 1 Great Vacation image

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.”

Vacation time can be an important way to maintain 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.

The coronavirus has added to that feeling of distance, making it difficult for many families to travel together. And the ones who have been able to manage it are tending to stay close to home or in the great outdoors—a number of national seashores and parks saw sharp increases in attendance in 2020.

Other families are using this time to lay larger-scale plans for that point in the future when they can reconnect with the ones they love. As you begin to gather ideas for that occasion, consider these tips.

5 Tips for Family Trips. Photo of a journal open to a vacation items checklist.
#1 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.
#2 Consider all inclusive resorts that appeal to all ages, have a variety of activities and dining choices, and often offer child care. Photo of a mother and her young daughter swimming in a pool.
#3 Be Clear About Money. Budget carefully in advance. Determine fiscal responsibilities up front. Photo of credit card, receipt and pen on a dining table.
#4 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.
#5 The Priority: Enjoy Yourselves! Photo of a large family holding hands and jumping into a lake.

Multigeneration travel is a popular vacation option for many families. It gives family members a chance to do many important and memorable things together such as learn about new places, share values and wisdom and recharge. Many families may also find that when they’re outside their everyday environments and having new experiences together, they open up more and are able to build closer relationships with one another, having conversations that they wouldn’t otherwise have at home.

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 Brian Shambo

Those experiences can run the gamut from camping in a national park to touring another country. 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.

Options like all-inclusive resorts 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. Popular family destinations such as Orlando can run approximately $100 per person per day for a seven-day vacation at select Disney All-Star 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 expenses to a minimum, suggests Brian Shambo, a Merrill Financial Advisor who speaks with many of his clients about their travel plans. “First, determine your destination and your list of what is important for you to do. Weigh your travel options and cut back on the less important things.” One tip for keeping costs down is to look for alternatives to hotels and non-traditional means of transportation. “Consider the costs between renting a car and using a ride-sharing app, and the difference in price between staying in a hotel or booking through a home-sharing app. In a digital age, you can really customize a trip to fit your needs,” 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.”

—Matthew Wesley, managing director 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 Matthew Wesley, managing director of the Merrill Center for Family Wealth™. “If your entourage is sizable, it’s essential to determine financial responsibilities upfront.” Wesley 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 Kids Guides, 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 remember, although where you travel can help set the tone for your trip, what’s most important is that you’re doing it together.

A private wealth advisor can help you get started.

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