I reassured myself as I walked to the check-in counter at Washington Dulles International Airport by running through my to-do list. Passport? Check. Tickets? Check. Three hours allotted to make it to the gate? Check.

I am not usually an anxious flyer. I've made several international trips and annually trek to my husband's native Trinidad to visit my in-laws. But this time we were headed south with an extra carry on -- our 5-month-old son, Simon.

Secured in the carrier against my chest, Simon wiggled and whimpered to be free as I bounced on my toes and practised my best apologetic face. I silently promised everyone I made eye contact with that I would drive to the Caribbean just as soon as a bridge was built. Next time, we'll strap floaties to Simon's arms and swim. Promise.

To compensate for my unpredictable travelling partner, I had thrown myself into controlling every other detail of our trip.


Since there is no direct flight from the Washington area to Port-of-Spain, Trinidad, we had to choose a layover. While we usually go through Miami, for this trip we chose Orlando, Florida. It offered a perk -- Walt Disney World. Surely a plane full of families headed to the most magical place on Earth would be forgiving.

I wished upon a star and kept planning.

While my husband dealt with purchasing the tickets and filling out the paperwork for Simon's passport, I consulted other moms about how to make our first flight as a family as smooth as possible. First lesson: Leave the bigger, bulkier stroller at home. Sure, it had plenty of pockets, cup holders and wheels that made for a smooth ride, but the simple Snap-N-Go would be easier to collapse and pass through security. Plus the detachable car seat could be taken on the plane if we were fortunate enough to have an empty seat next to us.

But I knew the real test would come in the air. Simon couldn't wipe his own nose, so how would he handle his ears popping? Lesson two: Nurse him or give him a pacifier -- anything to get his little jaw moving. I packed enough pacifiers to quiet a small day-care center.

After scanning Pinterest, I considered creating little bags of treats for our fellow flyers in hopes of fostering goodwill. Instead of wasting my limited time engaging in preemptive defensiveness, I decided to indulge in the small luxuries of new parenthood -- such as showering.

When the day of the trip finally came, I was ready. As we checked our luggage I took a mental inventory of Simon's essentials. A friend had advised me to "bring one diaper for each hour of travel," plus extras in case of delay, so I packed about a dozen for the first leg of the trip -- a 2 1/2-hour jaunt.

The bottles were in a clear plastic bag with the other liquids ready for the security inspection. I packed enough toys to keep him entertained through puberty. There was even a chew toy in case his first tooth decided to make an appearance somewhere over South Carolina.

Simon squirmed as I slipped off my shoes and walked through security. Having him in a carrier, not only did I had two free hands to heave the overloaded diaper bag onto the conveyor belt, I didn't have to struggle to get him out of the stroller in order to fold it up and send it through the x-ray machine.


A well-travelled mom friend advised me to place the collapsed stroller wheels-up on the conveyor belt to prevent it from spinning in place.

It truly takes a village.

Once I had my shoes back on, I used my free hands to pat myself on the back.

As we boarded, the flight attendants cooed over Simon and praised him for being adorable and well-behaved. (Read: quiet.) Unfortunately, there wasn't a free seat next to us. Simon would be a lap baby.

I tucked his diaper bag under the seat in front of me (easier to reach there than in the overhead compartment) and cuddled him. He resisted my efforts at confinement by squirming, stretching and whining loudly. I made a mental note to board at the last possible minute in the future. If anyone gave me dirty looks, I didn't notice as I alternately focused on shushing Simon and resisting the urge to order a stiff drink.

Then the best-case scenario unfolded: As the plane took off, Simon closed his big brown eyes and fell asleep. He briefly winced and rubbed his ears as we ascended, but otherwise he was lulled into a peaceful sleep by the engine's vibrations. The flight was beautiful and mercifully short.

It might have also made me a bit overconfident. For our next family trip, we are considering Europe.

It's a small world, after all.