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  • Writer's pictureKimberly M.

Traveling with a Toddler Part I: Survival Tips

Updated: Feb 18, 2022

My son and I took our first trip together in February of 2016. I had just gotten laid off from my job and JetBlue just happened to be offering a major sale on flights from D.C. to Puerto Rico. Coincidentally, my TrueBlue account just happened to have enough points to cover one full flight. It must’ve been a sign...this was "our" trip!

For a whole week I looked at the flights and hesitated booking it. How would I manage this trip alone with my son? How would he act on the flight? Would he enjoy Puerto Rico? What would we do? Would I even enjoy it? I researched website after website looking for advice, and looking for something to put my thoughts at ease. Eventually, something clicked. Something told me that if I didn’t do it now when I had nothing but time, that I never would. So I just booked it. It was a Wednesday night, and our flight was due to leave four days later on Sunday. I had no choice at that point but to prepare myself for this trip.

Flash forward to the end of the trip, we survived, and we both enjoyed it. In fact, we have traveled alone to Mexico and Costa Rica together since then and he often asks when we could go back.

So how does one survive through solo travel with a toddler? Here are a few things that helped make my trip easier:

Book your flights early in the morning.

I’m smiling to myself while writing this because I am NOT a morning person; however, when I travel with my son, I make it a point to book the earliest flight possible. Part of the reason of course is so that we still have a good portion of the day left when we arrive to our destination.

But the main reason is that because in the morning, they are fresh, you are fresh, everyone is fresh. I found that my son is much more well-behaved on the early flights, and airline staff as well as other passengers are much friendlier and more helpful. Try doing so in the late afternoon or early evening and you’re up against nap time, irritable people, and crowded airports.

Additionally, crack of dawn flights aren’t as likely to be full, and you’ll have more of a chance of getting the entire row to yourself!

Pay extra to choose your own seats.

Nowadays, it appears that airlines are doing everything they can to capitalize off of people wanting to choose their seats ahead of time. They are upcharging for “premium seats” and charging a higher fare just to have the option to be seated next to someone you are traveling with.

Unfortunately for single parents, it means possibly being separated from our child, because there are currently no laws requiring airlines to seat a minor and their parent together.

Some may book tickets thinking that they will accommodate, and end up getting sorely disappointed when they arrive to the airport and realize that the airlines aren’t requiring that they sit with their child. Instead, we must hope that another passenger will change the seat that they paid for to accommodate you, and we all know that most people aren’t that nice about giving up their seats!

If funds don’t allow you to pay for premium seating and no regular-priced seats together are available on that flight, don’t fear-- you still may have the opportunity to get seats together. In the days before the flight, keep checking back for new seats that have been released or for people who have changed their flights or moved seats.

I know that United Airlines usually releases an additional two rows of seats (or more) 2-3 days before a flight. Additionally, JetBlue will open up an additional 1-2 rows of seats if you have a special accommodation such as a peanut allergy or need special assistance. American Airlines will assign the premium seats at the gate for no charge if they are the only seats left.

Hitting the road instead of the friendly skies? Avoid a disaster and make sure you don't forget a thing with this ultimate road trip packing list!

Take the stroller.

Trust me here. It may be yet another thing weighing you down, your child may be very capable of walking, and you may not need it any other time during your trip...but you’re going to wish you had a stroller to strap them into when you need to quickly get to the gate, or when YOU need to take an emergency potty break while in the airport.

When you’re the only one traveling with your little one, you’ll want to do everything you can to keep them still when needed, and to be able to quickly transport them from one area to another when needed. Not to mention, the handles and storage basket underneath counts as extra hands!

I have never been so thankful to have a stroller than the time our flight from Costa Rica was delayed by an hour and we only had 40 minutes to make it through customs, back through security, and then literally RUN to the other side of the airport to make our connecting flight. Needless to say we were embarrassingly the very last ones that they were waiting for to close the door and take off...

If possible, take a carseat too.

Of course there’s always going to be the debate about using the carseat on the plane versus not...but safety issues aside (we’ll save that for a different post), I highly recommend taking a carseat just for the comfort of your little one.

It is a familiar source of comfort for them, and because of that, it’s much more likely that they’ll stay still and/or fall asleep in it during the flight. In addition, most car seats have cup holders which you’ll need to hold their sippy cups during the flight (please don’t forget the sippy cup)! I’m not going to lie, carrying a carseat AND a stroller AND having to manage a toddler is no walk in the park, but it is possible.

I also highly recommend buying a Gogo Babyz Travelmate where you can attach the carseat, buckle in your little one, and push them around like a stroller with one hand. In the other hand, you’ll have your luggage with four spinning wheels and a stroller bag that can be attached to the top of the luggage. You can also do this with regular two-wheel rolling luggage (like I did), but it may be a tad more challenging to get everything rolling in the right direction!

Don’t be afraid to ask for help.

I was pleasantly surprised to find that most people were very helpful and willing to help if they saw me struggling, especially in the airport. When going through security, other passengers around me were very patient and even helpful in getting all of my stuff through. Once I explained to the flight attendants that I was traveling alone, they let me board early to install his car seat, and even did little things to ensure he was happy, such as give him extra snacks or give him a pair of “wings” to make him feel important.

Give yourself plenty of time!

I make it a rule to always get to the airport at least an hour earlier than I usually would when I travel with my son to make time for the potential tantrums, extra potty breaks, or other toddler-related delays that may occur during my trip.

I also pay very close attention to the connection times between flights if not flying nonstop, and will refuse to book anything with less than two hours in between to allow time for the above, as well as give cushion for delayed flights.

If your travel includes one or more connections in addition to significant travel time after the flight, consider getting accommodations near the airport for a night just to relax and recover after a long day of travel, and to continue fresh the next day. You’ll appreciate it, and so will they.

Plan the trip around their needs and wants, not yours.

Of course when we visit a destination there are several things that we want to see, but when traveling with young ones we need to try and see the world through their eyes.

What would excite them the most?

How could you make the trip more interactive or entertaining for them?

Tell them about the trip beforehand, show them photos, and ask them what they are looking forward to the most about going.

Ask them what they want to do.

When you arrive to your destination, be flexible and try not to schedule too much. Toddlers are unpredictable, and while we may have the perfect itinerary planned out in our heads, your toddler is likely to tell you to shove your cute little itinerary right up your you know what.

They won’t nap when you want them do, WILL nap when you DON’T want them to, will have meltdowns at the most inconvenient times, and will almost always have to go to the bathroom at the worst flexibility is a MUST.

That being said, it is also very helpful to...

Relax the rules.

At home, we may have limited screen time, very specific naptimes and bedtimes, restrictions on what they can/cannot eat and when they can eat it, and boundaries on where they’re allowed to run around and play.

Well, when you’re on vacation with your toddler, both they and ultimately YOU will be much happier if you just let those things fly.

If watching their tablet or eating junk food and candy will keep quiet on a flight, let them have it.

If staying up late means allowing you to sleep in that much longer, let them do it.

If they want to get up and run around and stretch their legs while waiting on their order at a restaurant, let them (assuming they do not disturb the staff or other patrons...I was actually surprised to find that everyone was quite encouraging of this in Puerto Rico, Mexico, AND Costa Rica).

I’ve heard many a parent say that vacation is the “same shit, different scenery.” Well in my opinion, that’s only if you let it. It’s a vacation for them to, so let them relax and enjoy it while you sit back and enjoy the smile and joy on their faces.

Do something for you.

Traveling alone with your toddler will sometimes feel like a that you’re running alone. It is an absolute MUST that you do something for yourself.

For me, it means relaxing enough to order an adult beverage while we dine or sit on the beach together, or getting a bottle of wine from the store to enjoy after they’re in bed for the night. It means spending a little more money on my meal, or on ordering that dessert that I wouldn’t dare order at home.

You’ve spent the time and the money making this trip happen, and you are blessed to be able to do so alone with your child, so be sure to take care of YOU as well.

So there it is. If you are considering traveling alone with your little one, my advice is to JUST DO IT. Yes, it will be scary in the beginning, but once you take that leap you’ll soon discover that it is an experience of a lifetime that neither you or they will forget or regret. Don’t forget to take pictures!

Continue on to read Traveling with a Toddler Part II: What to Pack in Your Carry-On. Have any other tips? Feel free to share them in the comments below!


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