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Children / Family Travel

10 Tips and Activities for Traveling with Kids Over Winter Break

I’d like to think I am (literally) a road warrior with thousands of miles of solo travel with my kids. Of course, some trips are better than others and the older they get, the easier it is. It doesn’t matter how many years you’ve traveled, something usually goes wrong. I.e. Last week when we were flying back from Disney World, we literally lost our 8-year-0ld at the airport moments before boarding (sordid details here).

My biggest advice is to keep your sense of humor, hope for the best but be prepared for the worst.

Here are a few activities I’ve rounded up to keep the kids entertained:

Books on tape. This is a fantastic way to pass the time, particularly when parents need a break from being the entertainment committee. We rented several from the library including Flat Stanley, various Magic Tree House Collections and Classic Fairy Tales. For a fantastic age-by-age guide on the best audio books (starting age 2), check-out Travel Savvy Mom. Also, offers 100K+ titles you may download instantly to your iPod/ MP3.

Trip Journals. I’m made it a goal for the kids to record our major trips and what a treasure this has been to look back through their eyes. We are always on the lookout for fun roadside treasures to sketch in our travel journal, which is where we will also preserve many of our souvenirs. We also like to make funny signs and pictures to display when we pass cars. For younger kids, focus on pictures. For kids who need a bit of help, write down some keywords. We recently returned from Walt Disney World and I spelled out some highlights for my first grader: “New Fantasyland,” “Expedition Everest.” “Space Mountain.” He then took some of those words and wrote a story with pictures about them.

Maps. My kids are not directionally-challenged like their mother and they adore maps. I always print out Google maps and we also follow our route in our Rand McNally book of maps. When I’m really organized, I do some research and share fun things the children who live in that area like to do. Many times, this is where we’ll stop for our regular breaks. My phone’s GPS is also a source of fun and fascination as they can see real-time where we are traveling.

Coloring/craft projects. I have a travel easel for each child where they draw, make crafts and play games (I used a cookie sheet when they were younger because constantly picking up dropped items gets old, fast). Lately, I’ve plopped a big ol’ laundry basket in between the kids’ car seats replete with coloring books, notebooks, crafts, tape, pipe cleaners, crayons and markers. Easy access means mama won’t be turning around every five minutes to help (in an ideal world).

Movies (and lots of them). We are not fortunate enough to have a DVD player in our car so will bring our portable one. Because the car is noisy, I always bring a head phone splitter so both of my kids can listen with their headphones.

IPad/Nintendo DS. We have added an iPad to our entertainment mix and all those apps are a lifesaver for bored kids. We have a Wii at home and my kids are only allowed to play the DS on road-trips so it is a privilege they look forward to.  Confession: My son could play for hours and on 13-hour travel days, I often let him.

Dollar Store. I am convinced the Dollar Store was made expressly for kids on road trips. The week prior to our vacation, I assigned my kids various chores around the house. With the money they earned, I set them loose at the Dollar Store to relish in the glory of cheap plastic toys that I do not care if they get broken.

Travel Games. We have a great collection of travel-sized games that ranges from Hungry Hungry Hippos to magnetic playing cards. After losing numerous game pieces to our car’s Black Hole, we now keep them in an enclosed container. You can also find a lot of great printable car games online and don’t forget about the old classics like “I Spy” or the license plate game.

Books. My kids aren’t big readers yet so this won’t hold their attention for long but I’m hoping to spend at least a half-hour each day listening to them read.

Healthy snacks. In the past, our road-trip offerings have been solely junk food. While we will have treats, my goal is to take plenty of fresh fruit, nuts, trail mix, Pirate’s Booty and granola bars. I’m also giving each child their own snack bag so they don’t fight over the food (I speak from experience.)


Staying in Colorado for Christmas and want a quick getaway? Don’t miss our guide to the holidays at our mountain resorts. Everything from skiing with Santa to free s’mores to ice castles to Torchlight Parades for New Year’s Eve.

Amber Johnson
Author: Amber Johnson

Amber is the founder and editor of Mile High Mamas, travel writer and former columnist for The Denver Post. She is a passionate community builder and loves the outdoors. She has two awesome teens and is happily married to a man obsessed with growing The Great Pumpkin.

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Amber is the founder and editor of Mile High Mamas, travel writer and former columnist for The Denver Post. She is a passionate community builder and loves the outdoors. She has two awesome teens and is happily married to a man obsessed with growing The Great Pumpkin.


  1. Bookmarking this page. Great tips.

  2. I’m traveling alone with my kids to my parent’s and was a little overwhelmed. Love the books on CD options…tough to entertain them when you’re driving.

  3. I love the Dollar Store when we are going on a road trip. I love to wrap the toys from the Dollar Store, and give it to them along the way. I don’t have a DVD player in my car either, so I always bring my iPad with me for the kids. I let them watch movies, read, play games, and watch TV through the DISH Remote Access app. With the Sling Adapter hooked up to my DISH receiver we can access all our subscription channels and watch live TV on the road. I am so happy one of my co-workers from DISH gave me this tip. The kids love this option and it is such a lifesaver on the road.

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