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10 Mistakes to Avoid When Planning a Multigenerational Vacation

How to make a winter holiday trip memorable for the entire family


If you’ve decided to take your whole gang on a family vacation for the winter holidays, you’re not alone. According to a 2015 study by travel marketing organization MMGY Global, more than 40 percent of Americans reported taking a multigenerational trip the previous year. Virtuoso, an international travel agency network, cited multigenerational travel as its top trend in its 2016 study.

Travel is one of the most memorable gifts parents and grandparents can give to their families. Whether opting for a cruise, a theme park or a luxury resort, careful planning helps ensure a successful multigenerational trip.

We asked experts for the 10 biggest mistakes people make when planning multigenerational vacations and how to avoid them:

1. Planning everything on your own

When you’re trying to organize a multigenerational vacation, consider consulting a travel specialist. Not only can travel agents offer advice, they often provide insider access to deals and perks, such as shipboard credits for cruises or discounted cruise or hotel rooms.

“The bigger the group, the greater the need for working with a travel professional. Planning can quickly turn into a full-time occupation if you don’t know what you’re doing,” says Sally Black, founder of Vacationkids travel agency in Kunkletown, Pa. and author of Fearless Family Vacations: Make Everyone Happy Without Losing Your Mind.

2. Not designating a decision-maker

While you’ll want to consider all voices in the trip planning process, if you’re footing the bill, you’re probably the best person to make final decisions, says Black.

“The most successful trips are the ones with a group leader,” she says. “I’ll suggest everyone give me their wish lists. Maybe Mom wants a spa, Grandpa wants a golf course, and the kids want waterslides. This way, everyone will feel they had input.”

3. Avoiding discussions about money

“It’s hard to talk about, but the reality of how much you can afford is a very big deal,” says Black. It’s vital to have a clear budget.

For example, if your brood covets a week at Atlantis Paradise Island Resort in the Bahamas, with its waterslides, casino and golf courses, be aware that since it’s not an all-inclusive property, costs can quickly add up. If the group will want to splurge on a dolphin encounter, consider booking rooms in the more affordable Beach or Coral Towers.

Dreaming of a luxury cruise ship? Don’t blow your travel budget on airfare, when you can drive to a port instead. “Seventy-five percent of Americans live within one day’s driving distance to a cruise port,” Black says.

To manage expectations and avoid misunderstandings, have frank conversations with family members about who will pay for what. “Grandpa’s paying for the trip, but if your son wants to drink at the bar and his children want to play at the arcade, then maybe [your son] pays for that portion,” Black suggests.

4. Winging it at a theme park

At Walt Disney World or Universal Studios, families often open their wallets (wide!), yet give little thought to logistics. Without a solid plan, your family will likely spend a lot of time standing in line, says Seth Kubersky, author of The Unofficial Guide to Universal Orlando 2018.

“The first thing you should do when considering a multigenerational vacation at Universal, for example, is download their Rider’s Guide,” says Kubersky. “What is your kid tall enough for, and what is Grandma healthy enough to ride on? There’s nothing worse than going on vacation and discovering you’re not physically able to experience the attraction.”

Rather than aimlessly wandering, check out the touring plans developed by Kubersky’s colleagues. Based on traffic flow analysis, itineraries are designed to save time.

5. Not being an early bird

Since many parents are reluctant to pull their children out of school, multigenerational trips to theme parks usually happen during Christmas week or spring break when the parks are at peak capacity, says Kubersky.

“Even if you come on the busiest day of the year, you can still have a great vacation, but you need to be one of the first people at the turnstile before it opens for the day,”  he explains.

6. Wasting time and money at the box office

The biggest and most expensive mistake people make going to theme parks is waiting to get there to buy tickets instead of buying online, says Kubersky. “The only commodity you can’t get back on a vacation is time; every minute spent waiting to buy tickets is a minute you could’ve been on a ride.”

7. Wearing the wrong footwear

Whatever you plan, never underestimate the misery that blisters can bring on. At theme parks, “you definitely can’t walk around wearing flip-flops or sneakers without socks,” Kubersky cautions. “My biggest tip if you’re visiting Universal’s Islands of Adventure or Volcano Bay’s water rides is to take your shoes and socks off. Many rides have waterproof pouches built into the seats; you’ll have a dry pair of shoes for the rest of the day.”

8. Insisting that everyone stay together all the time

If you and the grandkids are active, while others would rather read, designate a spot as your family meeting point. Pack walkie-talkies or stay connected through cell phones or texts if you want to stay in touch.

“On a cruise, I have families who do activities together on the ship on sea days, and when they’re in port, everyone goes off to do a different excursion,” says Black. “Letting your group do things separately stimulates conversation at dinner, and brings the family together.”

9. Missing out on photo opportunities

On cruises, take advantage of ship photographers to capture candids or formal portraits. Digital photo packages are worth splurging on, says Black.

Or, consider booking a photography service such as Flytographer.com to meet up with your group during the trip.

10. Forgetting to relax

Above all, remember to treasure every moment. “The best multigenerational vacations combine balance, structure and enjoyment,” says Black. “If you have something for everybody, you’re golden, and everybody’s going to have fun.”

By Wendy Helfenbaum
Wendy Helfenbaum is a Montreal-based journalist and TV producer who writes about careers, travel, wellness, home and garden, and parenting. Her work has appeared in Woman’s Day, Costco Connection, Canadian Living, Parenting.com and many more.@wendyhelfenbaum

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