Traveling in the Car with Three Kids

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We’re heading to Boston this weekend to celebrate our eleventh anniversary with our three boys! Our anniversary is on a Saturday, and instead of the usual dinner out with a babysitter, we’re taking the boys to Fenway Park to watch the Red Sox play. We’ve decided to start exploring different baseball stadiums to add a unique cultural experience to our boys’ lives. This trip was a last-minute decision, as we hadn’t traveled all summer due to camps, sports, and new jobs. Plus, we were down to one car for most of the summer after our beloved minivan broke down on the highway during a camping trip in July. But now that we’re back to being a two-car family, we’re excited to hit the road in our new car!

Here are five travel tips for toddlers and young children:

  1. Pack Early! I always start packing at least a few days to a week before we leave. Dadjogger teases me about it, but I like having everything ready in advance. This way, I have time to remember any last-minute items I might have forgotten. Keeping the suitcase out lets me toss things in throughout the week as they come to mind.
  2. One Suitcase! I prefer to pack the whole family’s clothes into one suitcase, while the boys can have their own small bags for toys. Keeping everything in one suitcase makes it much easier to haul bags into the hotel. We usually have one bag for clothes, a cooler bag for snacks, and if the boys want their own “toy” bag, they are responsible for carrying it the entire time.
  3. On-the-Road Games! These are classic games I played as a kid that we’ll be introducing on our road trip. Anything that involves a little friendly competition among the brothers usually leads to a good time!
  4. Snacks! This one is a no-brainer, but I like to bring our own snacks and as much food as possible to avoid unnecessary stops along the way. I aim for meals that are healthy, quick, and efficient, which is easy to manage when we bring our own food. Of course, we’ll dine out once we reach our destination, but for travel days, bringing our own food simplifies life.
  5. Plan a Trip with a Special Attraction! For example, we’re going to Boston primarily to visit Fenway Park—a treat for the whole family, but especially for Billy, our baseball-obsessed son. He dreams of visiting ballparks across the country, even though he’s a die-hard Yankees fan. While we won’t be watching the Yankees, the Red Sox are playing a 4:10 game on our anniversary, which is perfect timing. We’ll have the morning for other activities, enjoy the game in the afternoon, and then head out for a nice dinner afterward. Another highlight will be the Boston Children’s Museum, which is exciting for all the boys but especially for Ben and Charlie. It looks amazing, with exhibits for kids of all ages, and visiting children’s museums in different cities has become a tradition for us. We plan to visit the museum on Saturday morning from 9 AM to 2 PM, and then head over to Fenway afterward. On Sunday, we’re deciding between the New England Aquarium or the Boston Museum of Science, based on a friend’s recommendation to skip the aquarium in favor of the museum. On the day we arrive in Boston, we plan to explore the city, explore the Freedom Trail and all the history that Boston has to offer, and try some new restaurants for lunch and dinner. We can use these trips as history lessons as there is so much to learn in Massachusetts. This trip will be packed with activities, and we can’t wait to celebrate our anniversary together as a family.

Tips from Experience

Take the Vacation! Life can be expensive, but I firmly believe you can still enjoy time away from home while staying on a budget. Take the trip—it might be challenging to prepare, but the memories you create will be priceless. Kids remember more than we realize. Billy still talks about our trip to Texas when he was five, along with all the memories from that adventure!

Finding the right hotel. Look for a hotel that’s clean, well-reviewed, and doesn’t need to have every amenity under the sun. We mainly use the hotel for sleeping and spend most of our time exploring the city. Our usual checklist for a hotel includes cleanliness, good reviews, and free breakfast. Even a grab-and-go breakfast saves you from deciding where to eat, waiting for a table, and gives you more time to explore because breakfast is already taken care of. We also like hotels with pools, but it’s not as crucial in the summer since our kids are in the pool every day at home. In the winter, though, a hotel pool is a great way to break from the norm. I have fond childhood memories of jumping into over-chlorinated hotel pools when it was snowing outside!

Traveling in the car is wonderful in that you have everything you need in one place and keep everything together!