Travel Envelopes – Traveling with Creative Kids Series

This is the first in a series of posts about traveling with Creative Kids. If you have any travel topics you would like to see featured in upcoming posts please leave a comment below or email me!

Sometimes we forget that in life the journey is as important as the destination. This can be forgotten even faster when faced with a long car ride.

With just a little pre-planning and creativity you can turn the car ride itself into a journey into creativity and create memories your children will cherish forever – even before reaching your destination!

Travel Envelopes:

This is a great way to add some surprise and spontaneity into your car travels. Having come from a family who traveled to see family every summer – the trip was inconsequential and vacation didn’t start till we arrived at our destination, I came up with this idea to make the journey as important as the destination.

Materials needed:

  • envelopes
  • Paper
  • colorful pens
  • stickers (to close the envelopes)
  • things directly related to your envelopes such as a pack of cards, spare change, camera etc.

Create broad categories for your envelopes such as BREAK TIME – for rest stops or when you want to take a break out of the car, CONVERSATIONS– prompts to get creative discussion going, IN CAR GAMES – ideas for the family to play while driving.

Once you have your categories it is a matter of coming up with one idea per envelope, writing it down and sealing it up. When you are on the road have family members take turns choosing an activity that fits, such as a BREAKTIME envelope when you are ready for a quick rest stop. I suggest you write the category on the outside of the envelope. The first time I did this, I didn’t have categories on the outside of the envelopes and ended up with a huge amount of breaks all in a row.

You can also keep a stack of envelopes in the glove compartment for those unexpected car rides. Here are some ideas to get you started.

Break Times:

  • Stop at the next rest stop and play a favorite card game
  • Pull over and have each member of the family take 1 creative photo
  • Stop at the next interesting store you see and buy a special treat. Include one dollar bill, or loonie or toonie (for Canadians) for each person to spend in the envelope.
  • Stop at the next two you come to and spend 15 minutes exploring together.
  • At the next rest stop play a running game – hide and seek, tag or another family favorite

In Car Games:

  • One word or one sentence stories – Create a story together building it one word or sentence at a time. Take turns and see where you end up. To make it more challenging for older children include a list of words that must be used within the story.
  • Treasure Hunt – create a list of things to look for while you are driving. Copy a list for each person and see who can find everything on their list first.
  • Name that tune! Create a playlist or listen to your family’s favorite music. Play the first 30 seconds or s of each song, turn it off and have everyone try to name that tune.
  • I’m going on a trip…” The person who starts chooses a simple pattern, such as everything must begin with a specific letter, everything must be a vegetable, or each item must start with the letter of the person’s name, etc. They then say: “I’m going on trip and I am going to bring Apples” The next person must say “I am going on a trip and I am going to bring _____” If their choice fits the pattern, the person who chose the pattern allow them to come on the trip. Everyone takes turns guessing and listening to each others answers until everyone figures out the pattern and can come on the trip.


Choose specific questions to ask that will get conversation rolling. Questions should be open ended and not include yes or no answers. Have everyone in the car answer, it is a great way to get to know each other better and get everyone involved.

  • If you could be President/Prime Minister for a day, what is one thing you would do to make our country better?
  • What three goals would you like to accomplish in the next year?
  • What special family activities would you like to do this summer?
  • What is a new hobby you would like to learn/get involved with?
  • What is your favorite breakfast? Lunch? Dinner? Snack?

Having envelopes is not only a great way to entertain the family on long road trips, it is great for relationships too. You can customize break times to include such things as playing a favorite game, the winner receives a 5 minute shoulder rub, or stopping to buy a treat but buying something you know the other person will love. In Car games can be customized to things you love. On a recent 16 hour drive we played our own versions of our favorite cooking shows. The Chef Abroad Challenge involved dreaming we won a culinary tour anywhere in the world, all expenses paid and discussing where we would like to go. A Top Chef quickfire involves the challenge of creating a dish that described the other person, our likes, personality all translated into food. I was a sweet, spicy, semi-healthy, heart shaped pizza with staggered toppings (so no two slices would be exactly the same).

The car is also a great place for conversations you wouldn’t think of normally having. With envelope prompts it becomes very easy to bond over your hopes and dreams and make plans for the future.

How does your family entertain themselves during long car rides? Have any creative travel envelope ideas? Please share below!

Posted in Activites/Games, Series, Traveling with Creative Kids.

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