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How to Plan a Fun Summer Trip With Your Grandchild

Here are some tips to help prepare for a seamless — and entertaining — travel experience for both generations

By Carol Morgan Milberger

I always thought a special bonding trip with each grandchild was a wonderful idea. Age ten is perfect, the ideal time while they still adore me, can endure travel delays but don't miss their friends too much.

Then COVID extended the timeline, and all of a sudden, I realized my oldest grandchild had turned eleven. She'll attend middle school soon, so if I'm to cement our bond while the magic of childhood is relatively intact, I needed to get moving. I developed a tentative trip, then asked for her parents' blessing.

The Jefferson Memorial in Washington D.C. Next Avenue
Having a great time while traveling with children takes planning, awareness and communication.  |  Credit: Grant Czerwinski

Mandy (not her real name) was thrilled at the idea of visiting Washington, D.C. We'll tour the nation's capital, then spend time with my family in Maryland. Her eyes widened when I mentioned the Washington Monument and Lincoln Memorial. Mandy leaned forward and squeaked, "We studied the national monuments at school!"

Working out, some downtime and morning coffee are important to me, whereas Mandy wants lots of pictures of monuments.

Having a great time while traveling with children takes planning, awareness and communication. Consider the following tips to help produce a trip that is fun and rewarding for both generations.

Tips for a Successful Trip

Planning is part of the fun. Set the travel date early. I was surprised at how much of her summer was already blocked off by March, and glad we found a time that worked for both of us. Mandy immediately told her friends about the trip; clearly she was excited. I told her we'd start with the Hop-on Hop-off bus, since it would allow us to see the hot spots and spend time exploring what interests us most. This flexibility is perfect, since we can decide what we want to do while there.

Mandy and I got together to brainstorm questions and the top three things she wanted to do on the trip, then we reserved the flight together. I'll book a hotel, then wait a month or so before our next planning session.

Take individual desires into account. Working out, some downtime and morning coffee are important to me, whereas Mandy wants lots of pictures of monuments. I'm trying to take energy level, attention span and safety into account for both of us.

I'm a fan of lists, and will rely on our top three to five things when planning and traveling. This will help me remember that pictures are among her top three desires, so I'll remain patient while she strives for ten perfect Reflecting Pool photos.

I might even list what I want to avoid. I'm not a fan of long lines, so I'll plan outings to avoid crowds. If my plans don't work, we might pass the Smithsonian line and return later in the day. We'll take Mandy's dislikes into account as well. The dislikes conversation can branch into a discussion of concerns, which is also a great conversation to have.

A grandmother smiling with her granddaughter. Next Avenue
The author and her granddaughter  |  Credit: Courtesy of Carol Milberger

Make lists. I'll create a packing list with Mandy. It's easy to mark items off as they go into the suitcase, and this will ensure we take everything we need. When I mentioned ponchos as a great summer option, none of my grandchildren knew what I was talking about. We marched down the hall to the utility closet where I unfolded a lightweight orange poncho.

The younger two loved it, but Mandy said she'd rather carry an umbrella.  (I'll pack an extra poncho but keep in mind she is old enough to select fashion over getting wet.)

Discuss limits. I'll find out what parental rules regarding electronics (screen time, social media, texts, calls) will be in place during our trip. I told Mandy that D.C. is different than our small town, so we'll need to stay together while traveling. I asked her to gather friends' addresses so she can send postcards. Mandy says she knows about postcards, but I imagine addressing one will lead to a wide-eyed conversation about how we did things "in the old days." I'll ask her to pack downtime activities like reading, drawing or journaling to engage her while flying or in the evenings.


Attend to siblings. Mandy's siblings will be disappointed when they discover they're missing a trip and airplane ride, so we are trying to soften the blow. Of course, I'll take each sibling on a fun trip when they turn ten or eleven. Mandy and I hold our planning sessions while the siblings are busy with other activities. Mandy's parents will take the siblings on an outing while we are gone and Mandy will return with a fun gift for each of them.

Be prepared. Make sure you know about allergies and medication for your grandchild. TSA doesn't require identification for children under 18, but suggests checking with individual airlines. Keep in mind that if you are flying with a child that looks 18 (or age your airline considers as "adult"), you might need to prove their age, so it is a good idea to have legal ID or a birth certificate on hand. I plan to carry a signed medical release form so I don't have to wait for parental permission in case of emergency.

My goal is to say "yes" to every one of her requests, without running out of time, money or energy. 

Have Fun. I hope to pack in as many treats, views and experiences as possible. My goal is to say "yes" to every one of her requests, without running out of time, money or energy.  Who knows, I may end up with a lifelong travel companion!

Strengthening Our Relationship

In addition to fun, I consider this trip (as well as other methods of reaching out and connecting) to be mental health insurance. The teen years can be extremely tough. When, sometime in the future, Mandy feels lonely, excluded or unworthy, I hope she'll remember that no matter what, her grandparents love her.

While her grandfather won't join us on this trip, she can count on him to make silly faces, tell ridiculous Dad jokes, and be incredibly patient and kind. I'll always listen, cook healthy meals, and spend time with them. All these actions translate to love, something grandparents excel at.

Carol Morgan Milberger
Carol Morgan Milberger, Ph.D., is a retired psychologist who enjoys writing about various topics, including health, parenting, work, family, aging, and resilience.  Her work has appeared in WIRED, INSIDER, HIPPOCAMPUS, and elsewhere.  More information and essay links are provided here. Read More
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