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Celebrate Your Family

Planning Your Best Multi-Generational Vacation

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Planning Your Best Multi-Generational Vacation
Planning Your Best Multi-Generational Vacation

Our family of 14, ages 11-70, entered the gates of Walt Disney World’s Magic Kingdom with one goal–start our multi-generational vacation with a ride on Splash Mountain.

We Midwesterners would have had every excuse to begin our first day with complaints about the cool and rainy weather we hoped to leave at home. But we left our expectations and disappointments behind, instead, pulled 14 Mickey Mouse rain slickers over our already damp clothes, and headed to the log ride.

I focused on the fact that it was the first time my stepchildren had been to Disney World, the first time my husband and I had been there together, and the first time my children, my brother’s family, and my parents had all vacationed with us.

Splash Mountain would be a new experience for some of us and nostalgic for others. The plan for this first blended family, multi-generational trip included sharing this inaugural moment. On that ride, we formed a new camaraderie, chattering as our log cars climbed up the incline and screaming as we plummeted down the hill. For me, that vacation still represents the purpose of trips like this–to enjoy the people we love and make memories with them.

Magic-Kingdom-Splash-MountainDespite the challenges inherent in traveling with a large group of family members, people usually remember these events as “good times,” even many years later.

The greater the age span among travelers in a multi-generational party, the more variety (and patience) required. From theme parks to camping trips, many destinations provide amenities and activities that can cater to a range of ages, as well as the range of interests and levels of activity.

MMGY Global Portrait of American Travelers forecasted that last year nearly half of all Americans would be taking a multi-generational vacation. Perhaps, the increase in this type of travel is indicative of the trend of Americans to spend money on experiences rather than material objects as well as the increased availability of travel options to accommodate these families.

Travelandleisure.com suggests “grandparent-friendly” destinations that also provide fun and entertainment for younger generations craving adventure, including river and ocean cruises, train journeys, all-inclusive family resorts, dude ranches and even safaris.

A multi-generational trip is not going to be everyone’s dream vacation. Some family members envision a cabin in the woods, while others relish the lights and sounds of Las Vegas. Some want to relax to the sound of ocean waves, and others are ready to ride the waves. In general, family vacations involve compromise; this is even more true in multi-generational scenarios.

Amanda Vallone, co-owner and marketing director at Roseborough Travel in DeLand, Florida, has traveled the family vacation route many times and has also led tour groups of up to 75 people. She and her husband have vacationed with four generations of family members, ranging in age from her two-year-old daughter to her husband’s 72-year-old grandmother.


Vallone warns that initial family meetings to brainstorm vacation ideas often lead to frustration and a lack of consensus. To help expedite the planning of a multi-generational trip, she recommends that families appoint one or two decision makers who check in when larger decisions need to be made. “I highly recommend a group leader who brings info back to the larger group and presents options,” said Vallone. “Families can then create a beautiful plan around that core plan.”

Disney World BannerFor our Disney World vacations, we rely on my mother, the consummate WDW travel “agent.” In addition to reserving dates for a timeshare, she plans a tentative agenda for the week that ensures that our entire group will share specific experiences together, such as that favorite ride or dinner in the evening. In between, each family unit has time to themselves.

“We have found what works best for us is not to expect everyone to be on the same page,” Vallone said. To offset this, their family also relies on a basic schedule that includes designated meeting points. For Vallone’s family, that meeting point involves dinner together [make reservations!] after spending the day apart pursuing individual interests and activities.

“Throughout our 17 years of traveling together, meeting for dinner has always been our rule,” Vallone said. “During the day, we have grand adventures on our own time and at our own pace, then at dinner, we come together to share fantastic conversations about everything we did. That’s the best guideline I can give for family travel.”

Tips for planning your multi-generational vacation
If planning a multigenerational vacation seems overwhelming, there’s hope! Travel agents are well-versed in aiding helping navigate what can be a daunting planning process.
Vallone has experience not just as a traveler, but as an expert in the travel industry. In addition to her own family excursions, she helps families plan their trips through Roseborough Travel every day.

Vallone said that the basic process begins with a family making the following decisions:

  1. Choose a destination or the type of destination. A family may know that they want to visit New York City and may even know what they want to do there, e.g. stand in Times Square or visit the Statue of Liberty. On the other hand, they may not know the exact locale but have agreed on a tropical getaway with lots of sand and sun.
  2. Provide a timeframe. Family members need to agree on a length of time and specific dates, one of the biggest challenges for younger generations working around school and job schedules. But these dates especially important for planning. “Travelers often want to know flight information first, but we have to check accommodations first,” said Vallone. “There’s no sense buying plane tickets if there’s nowhere to travel to.”

Once this information is provided, the travel agent can then narrow down plans based on desired activities and flight schedules. Vallone and her team ask families a series of questions to help customize the vacation plan. Agents then help with arranging transportation between the airport and resort/destination, researching desired amenities, and scheduling special excursions.

The aid of a travel agent can be especially crucial when traveling involves elderly family members or those with special needs. An agent can help ensure particular accommodations such as handicap access and refrigeration for medication. Agents also help families consider activities such as hop-on/hop-off tours for those who are less active, while suggesting more physically demanding excursions for more active members of the family.

“Agents give their recommendations of options, then the families make all the choices,” Vallone said.

When planning a multi-generational vacation, one of the best choices may be to lower expectations for the “perfect” vacation but have high expectations for spending time with the people you love most.

Tips for making the most of your multi-generational family vacation

Be prepared–Bandages, good walking shoes, and water bottles are essential, but so is space. Don’t over plan the day; instead, leave room for rest, spontaneity, and unexpected events. Two of our WDW vacations have involved trips to the emergency room–one for the flu and another for a somersault down the hotel stairs to rival a Cirque du Soleil act.

Be flexible–If every person goes into a trip with a rigid list of to-do’s, a lot of people are going to end up disappointed. Wants can vary as much as personalities and ages. A certain amount of flexibility–not just in the variety of activities available but in attitudes–can make a positive difference for everyone.

Be patient–Patience especially comes in handy when traveling with very young children and elderly family members who need to take things at a slower pace. Taking time for naps in the middle of a busy day may seem like a waste of time, but these breaks can help ensure everyone stays physically and emotionally healthy and that a vacation actually feels like a vacation.

Be gracious–We often go into vacations with high expectations–not of ourselves, but of others. But babies get fussy, teenagers will bicker and zone out, and grandparents and great grandparents get weary. Appreciate what each generation brings to the trip–small children reawaken wonder, teenagers and young adults can bring energy, and older generations remind us to take opportunities to relax and reconnect.

Be ready…to make great memories.

For more information or to talk with a senior care advisor at no cost, call Aging Tree at 1-866-320-8803. We can help you and your family navigate the many aspects of planning for your senior living lifestyle.


Amanda Eastep

Amanda Cleary Eastep is a freelance marketing writer for businesses and universities at Word Ninja. She believes words should not only inform, but also offer encouragement and hope. She blogs about faith, family and life change at “Living Between the Lines.”

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