Effective Tips For Making Multigenerational Travel Fun

Traveling with children is stressful enough without the added pressure of having extra people around judging my parenting capabilities during some of the most difficult parenting situations - long flights, potty training days in an airport, meltdowns from the overwhelming nature of everything being new. It used to feel like the thought of my parents and/or in-laws traveling with us on family vacations to witness that show on the road only added to the pressure.

Needless to say, I’ve come a LONG way.

I have found that traveling with your extended family is one of the greatest gifts you can give to yourself, your spouse, your children and especially your parents and in-laws.

Diana's extended family on vacation in Orlando

Diana's extended family on vacation in Orlando

I always wonder what my mom, even my in-laws think about traveling with all of us. I knew if I asked them, I wouldn’t get the whole scoop. Recently, a friend put me in touch with a Mother and Son traveling duo, and by the time I had discussed the topic of multigenerational travel with both of them, I had a treasure chest full of perspective on the challenges and how to solve them.

Justin, a dad to two kids under five years old, regularly plans trips all over the world with his family of four and their extended family including his mom, Barbara, and her husband; his dad and his dad’s wife; as well as his in-laws.

Including Justin's kids, Barbara has seven grandchildren. She’s a huge travel nut, but aside from her personal travel schedule, she regularly- up to four or more times per year- ventures out with her husband on multigenerational trips with her kids, step kids and their families.  Both Justin and Barbara shared the secrets to their multigenerational travel success. Here’s what they said:

Why take the show on the road? Isn’t it easier to just have relatives come to your house or vice versa?

  • Justin’s Take: When you travel someplace new with your family, you get to enjoy the sights, sounds, smells and flavors around you, and it brings you all closer together because the normal daily routines and distractions of everyday life at home fall away.
  • Barbara’s Take: I think doing this is very healthy- it's good for children because there is something very wholesome about all being together even if it means a little chaos. It’s a growth experience for everyone. Kids experience being a part of a larger family unit and I think that grounds them. 

Is it hard for the one making the plans to keep everyone happy?

  • Barbara: You really just have to ask everybody what they are looking to get out of that particular trip. What are everyone’s goals? Once you know the answers to that question, then choose a place that has something for everyone.

Speaking of choosing the right destination, how do you do that? What destinations work best for multigenerational trips?

  • Justin: I recommend to anyone who hasn’t done it yet to try a cruise. With a cruise, no one is ever far from a buffet or a nap, no matter who needs it. That gives everyone built in flexibility right there. Also, transportation is already taken care of. Most cruises have a variety of activities built in that appeal to all ages. 
  • Barbara: Pick a place that has something for everybody. You don’t want teenagers pouting in the corner while grandma is yucking it up with her sisters. Likewise, don’t drag grandma through Disney if that’s not what she wants.

What type of accommodations does your family typically look for when planning multigenerational trips?

  • Barbara: We’ve done it all. Rented houses, done timeshares, cruises, you name it. So, for us the answer is to switch it up and keep things unique.  Recently, we rented a HomeAway vacation rental in Cape Cod and we were able to accommodate friends at the beginning of week and then family at the end of the week. Having a house made it so comfortable and we were able to create lasting memories. Right now I can picture myself sitting on the front porch with my three-year-old grandson talking about cars. I’ll always remember that seemingly small moment as something much bigger.
  • Justin: We find vacation rentals to be a better value for the money, and it makes it easy to have everyone in one place. I like to make sure I’m in walking- or short driving distance from grocery, shops and other main venues.

What about the kids? Do they enjoy traveling with extended family?

  • My Own Take: My kids wouldn’t know their three cousins (who live in London) very well at all if it weren’t for our multigenerational trips. Sure, they see them every other year for the holidays, but that’s only for a few short days. Last spring, my family, Hubs’ parents, and his brother’s family all descended upon Walt Disney World. Because of the new adventures they shared in a new place, my girls and their older boy cousins are now connected for life. They email, Skype, send birthday cards to each other and talk about each other in a way that you’d think they were just down the street, rather than across an ocean.
  • Justin: Many times, a vacation can mean no meals to cook or errands to run, so kids get concentrated time with the family members they’re traveling with. For us, the travel my kids have done with their grandparents has intensified those relationships.

What are the best things about traveling with extended family?

  • Barbara: Entertainment and brainpower! You get to use other people’s strengths for the good of the group and you have built-in entertainment because with many people of many ages, there is always somebody doing something. You can join in if you want to.  
  • Justin: The opportunity to divide costs, of course and, especially if your parents are longing for that quality bonding time with the kids, some help with childcare and babysitting.

How do you handle the babysitting offers on multigenerational trips? I’ve personally had a hard time finding the balance between letting grandparents have quality time and not leaving anyone feeling exhausted or taken advantage of.

  • Barbara: Everyone has to talk about these things in advance and be honest with their responses. It’s up to the parents to make sure they know what their parents or relatives are looking to get out of the vacation and how much time they are willing or wanting to babysit. Also, the ‘babysitter’ has to be honest about how long at one time they are capable of handling the kids. Maybe they want the kids for a few hours each day, but they can’t handle hours and hours on end without a break. If it’s hammered out in advance, it takes the pressure off of everyone and no one will have unmet expectations about sharing the care-taking responsibilities.
  • My Own Take: The mistake we make is not talking about it upfront. Barbara’s spin on it is an “ah ha moment”. We have traveled with everyone under the sun in our family and sometimes Hubs and I are the selfish ones. We feel like if the family hasn’t seen the Littles that they should ‘want’ to spend all of their time with them. It’s eye-opening to understand it from all perspectives.

Barbara and Justin both agree, relationships will change over time and every new trip will have its own unique feel. As long as everyone is willing to keep open lines of communication then multigenerational trips can become the new norm for your family vacations.

Diana Heather is the Chief Mom, both at home to her two girls and at Totsy.com. You can follow Diana on Twitter @ParentingsATrip or read more at her blog: ParentingsATrip.com.