How We Make the Most Out of the Holidays While On the Road

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Every year we have the same Great Debate around this time of year: whose family will we spend Thanksgiving with and which party gets to travel? As my children are all over 18, this is especially difficult because they each have girlfriends or husbands that they’ll want to see on the holidays as well. Since my daughter, Mallory, got married, this added another branch of our family that is brought into the debate (and, luckily, we love her new mother-in-law). However, both The Cuban and I have parents that live 3-4 hours away from us and we usually try to see them for either Thanksgiving or Christmas and take turns with them. The Cuban loves to drive on road trips which allows me to settle in with my travel pillows and blankets. Depending on which of our children travels with us, we have some things that have become tradition while we’re out on on the road.


As you’ll see, we love to take road trips and sometimes use the RoadTrippers app to help us navigate places we didn’t know existed. Here are some other things we do to pass the time. Side note: make sure you leave earlier than planned if you’d like to stop as much as we do while traveling.

  • Listen to Podcasts 1 of 8
    Wait...Wait...Don't Tell Me!

    Since we can't all agree on what music to play in the car, the one show we can all settle on is NPR's Wait...Wait...Don't Tell Me! It's quick, witty, and full of current pop culture and news. We guess along with the contestants and since I subscribe to the podcasts, we have enough of them saved up to take the iPad on the road with us as we travel. I may or may not have a secret crush on Carl Kassell's dulcet tones and would like to have him on my voicemail.

    By Ben Schumin (Own work) [CC-BY-SA-3.0], via Wikimedia Commons

  • Take a picnic lunch 2 of 8
    Pack a picnic basket

    Fall weather in Illinois is always unpredictable. On the off chance that we get to stop while traveling, however, we try not to spend money on food since we're going to be eating once we get to our destination. Instead of ruining our appetites for my dad's Cajun Spaghetti or the pie-for-breakfast-morning of Thanksgiving made by The Cuban's mom, we do it up picnic style for the road. We throw in snack foods that aren't messy or require refrigeration. Everyone in my family loves pistachio nuts, Gala apples, and fruit strips (much healthier than those thin roll ups) and we each take our own water bottle that we re-use.

    By Jeremy Noble (Flickr: basket) [CC-BY-2.0], via Wikimedia Commons

  • Be comfortable 3 of 8
    Take a travel pillow

    Since my boys are extremely tall (6'2 and 6'4) it makes it hard for me to recline my seat on road trips so I take along my favorite neck pillow so I can nap. I'm a champion napper and if it were an Olympic sport I would probably be wearing several Gold medals. My family knows that I function better if I can grab a quick snooze and they accommodate me by wearing headphones so they're entertained when I sleep.

  • Take pictures of passengers 4 of 8
    Take some car pics!

    It's rare that we go on a road trip and I don't pull out my smartphone to capture the kids. Illinois is extremely flat, but that doesn't mean it's not pretty sometimes. I usually Instagram our road trip and grab pictures since I have a captive audience. When I look back at my photos I can remember where we were traveling to and where we were headed. This picture is from when we traveled for a family vacation to Galena, Illinois.

  • Photograph the landscape 5 of 8
    Get out of the car!

    Speaking of flat Illinois, one of the things that has become increasingly familiar is the wind turbine farms that are popping up all over. Occasionally, I request that we stop and take pictures of the things we're passing. The kids like taking a bit of a break so they can stretch their legs and, if we're traveling with the dog, it helps to give her a potty break, too.

  • Multifunctional Clothes 6 of 8
    Take a scarf

    Wearing scarves while on road trips helps in two ways: 1) you can fold it up and use it as a pillow or neck rest, and 2) you can cover your eyes when it gets bright. A third option is that it keeps you warm depending on the weather, but it always adds a layer to your wardrobe. Depending on how long of a trip you're taking, it will extend your wardrobe as well. 

  • Listen to and share music 7 of 8
    Music for everyone

    We know that trying to settle on one music station or CD doesn't always work, so everyone has their own set of headphones for road trips. (Although, have you tried the "Road Trip" radio station on Pandora? It's amazing.) If someone really wants the family to listen to something, we take turns using a cord to plug in our phones to the car, but usually we're on our own unless we're really feeling like a sing-a-long. No one in my family finds my knowledge of every lyric to The Sound of Music particularly fascinating anymore. 

    By jimmyweee (PrioritiesUploaded by russavia) [CC-BY-2.0], via Wikimedia Commons

  • Play travel games 8 of 8
    Travel Catchphrase

    Our family loves to play the travel CatchPhrase game (even when we're not on a road trip!) and it's something even the driver can play - even though you shouldn't make him hold the game. We work on teams and split up the rows of seating in the car. The objective is to have your partner guess the word by giving only clues so this makes for a perfect game in the car. This is the version we take with us. It is our favorite game while traveling and when we get to our destination. 

Article Posted 2 years Ago
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