First Baby Free Vacation

3 minute read

First baby free vacation

Parenthood is exhausting, but I’m really proud of the way Aaron and I are raising Max. It’s fair to say that most days we are raising a pretty happy kid. That’s why when Aaron had a work related trip to San Francisco, we jumped at the chance to drop Max off with his grandparents, Pops and Bebe, in Chicago. But this was going to be a trip loaded with firsts - first flight, first night away from home, first extended time away from us - so needless to say my anxiety was at an all time high. But like most things in life, reality rarely meets expectations.


Expectation. A number of people gave us the advice to travel early, but we didn’t really take it to heart. When Max was 4 months old we took him on his first road trip to Chicago (14 hours). Even though we split the driving across two days, the drive was anything but easy. Max had just started sitting up and was not happy being strapped in a carseat. That problem has only gotten worse now that he is older and is in perpetual motion.

I kept telling myself that all kids are different and that one friend’s horror story wasn’t necessarily going to translate to Max. But in reality there is no way to know how your child is going to react to a new experience. I naturally assumed the worst and tried to plan for everything.

Reality. We gave Max a dose of tylenol in the morning in case his ears bothered him. We arrived at the airport early so Max could run around. Two outfit changes later Max was rubbing his eyes as our flight was being called to board. Everything was going as planned, then an announcement came on that our flight was delayed for an unknown amount of time. For the next hour and a half, we used every trick to keep Max awake and entertained. Somehow we succeeded and boarded the plane with an exhausted baby. Max fell asleep before the plane took off and woke up as the plane was taxiing to the gate at our destination. I breathed a huge sigh of relief. We made it through Max’s first flight.

The Flight

Take aways.

  • I don’t know if the tylenol was necessary, but until Max can tell me the pressure doesn’t bother him, I will continue to give him tylenol before a flight.
  • Don’t worry about getting your child an exciting new toy. You are going to have an unbelievable amount of luggage already. If your child is like mine, then the on-flight magazine or whatever is in your purse will be exciting enough.
  • Check your bags!
  • Special Snacks. While special snacks are great, they only distract your child for about 5 minutes.

Carry-on essentials Here are the items that helped us the most.


Expectation The plan was to drop Max with Pops and Bebe near baggage claim and circle back through security during our 1 hour layover. Since Aaron was on a work trip and therefore was on a less flexible schedule, I was going to carry Max and his things down to the meeting point, then circle back up around through security and join Aaron for the flight to San Fran.

Reality We walked off the plane and Pops and Bebe were standing there waiting for us (with a huge bag of Garett’s popcorn!). They were able to get guest passes to go through security. We kissed Max goodbye, he happily reached for Pops and left us without a tear.

The Handoff


Expectation. Max is a pretty easy going baby, but he had never spent the night away from home. We were nervous how he would be in a new house and a new room.

Reality. Bebe went above and beyond to make Max’s room away from home comfortable. And he slept like a baby.

Max's room at Pops and Bebe's house

Here are some of the details she added.

Decor details that Bebe added to Max's room.

Once we were in San Francisco, Aaron and I fell into our child-free days amazingly easily and had a great and relaxing time. How did your first trip away from baby go?