Traveling for Two: The Toddler Edition

Another one from the Hauling in Heels archive! This is a follow-up I did on traveling with a baby. I originally published this in the beginning of 2015 when my daughter was around 16 months old. It’s crazy how some things no longer apply (RIP In this post, I compare the trips and give my advice based on those experiences.

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Toddler on Board

Oh man.  This is gonna be a long one.  Grab a cup of coffee/tea/wine (no judgment) and settle in for some heavy reading.  After the popularity of “Traveling for Two”, I’ve decided to do a follow up based on my most recent travel experiences, which were my daughter’s first since she officially began toddling two months ago.  Our trips encompassed different ends of the travel spectrum: one 5-day vacation to Florida; and one 7-day business trip to Hawaii.  There’s a lot of ground to cover so I’m just going to get right into it.  


Florida – The flight to Florida was only 2 1/2 hours so we decided to keep our daughter on our laps.  We booked our flights to be in the middle of the day to coincide with her nap time.  

Hawaii – Twelve hours there and ten hours back (plus a stop each way)?!?!  We balled out and bought our daughter her own seat.  As for timing, there was no avoiding less than ideal flight times.  I had to be in Maui by Sunday evening, which meant a 6am flight out of JFK.  The long distance plus five hour time difference meant a red eye on the way back was unavoidable.  

The Verdict – If you can swing it, the extra seat is worth it.  The added freedom for you during nap time is invaluable. You’re free to eat/go to the bathroom/wave your arms in the air like you just don’t care.  The only issue was that while our toddler can nap just fine in her car seat, she couldn’t get comfortable enough during her “nighttime” sleep (she’s a stomach sleeper) on the red eye from LAX to JFK. This meant she had to sleep on me the whole way. Therefore, I didn’t sleep at all (but I did get to watch Pirates of the Caribbean)(and Ian Ziering was sitting in the row in front of me)(90210 rules!)(#teamkelly).  Anyway, even if she didn’t always want to be in it, it was really nice having it as a place to put all of our stuff, and it was even nicer not having a stranger there. 

As for timing, shorter nonstop flights are of course easier. Timing ours during her nap was smart (pats self on back).  If a long distance flight is unavoidable, as it was for us, take the anything goes route, and just get your little one back on schedule at your destination.  


Florida –  Since my mother-in-law is so awesome and helpful, she bought all of our favorite brands of diapers, soap, etc.  My husband and I hardly needed to bring anything!  Here’s what we packed for the little one:  

  • Two outfits per day
  • Two pairs of shoes: sneakers and adorable but dreadfully uncomfortable rattan sandals (both of which she outgrew while in Florida)
  • One set of pajamas per night
  • A sun hat
  • Bottles and formula
  • Pacifiers
  • Emergency change of clothes for the plane
  • Enough diapers/wipes/cream for the airport and plane ride
  • A meal in case we couldn’t find anything good at the airport (we did – the JetBlue terminal at JFK is awesome)
  • A favorite book  

Hawaii – Had we been traveling within the continental US, I probably would have ordered from (note: today this would be Amazon, edited for the rest of the post) to the hotel, but shipping was expensive so we packed everything.  Our Hawaii packing list included everything listed above for Florida, but we quadrupled the plane supplies.  The additional items were:

  • Diapers/Wipes/Cream
  • Coconut Oil
  • Baby Soap (this one doubles as laundry and dish detergent)
  • Bottle Brush
  • Baby Sunscreen (we tried this one with great results)
  • Swim Diapers
  • Baby Sunglasses (these are awesome)  

The Verdict – In the world of packing for your baby, if you have the room in your suitcase, are going somewhere relatively remote, and aren’t renting a car, then more is more.  Otherwise, Amazon is your best friend (though Amazon is probably already your best friend).  

Getting to/from the Airport

Florida – We used Uber with Car Seat option on the way to the airport since we weren’t bringing our own car seat.  In Florida, my husband’s parents picked us up, and they have a car seat installed in their car for all of their grandkids.  

Hawaii –  We used regular Uber to get to the airport and then we (and by we, I mean my husband) installed our own car seat.  Ditto for the cabs once in Maui.  

The Verdict – Uber is awesome.  And so is my husband, who could seriously enter a speed car seat installation contest.  

Getting Through the Airport

Florida –  We didn’t check our bags to Florida. We had two rolling carry-ons, one large purse for me, one backpack for the husband, and one diaper bag for the baby.  We wheeled the baby around in her travel stroller, which we gate checked.  My husband rolled the suitcases with the backpack on his back, I rolled the baby in her stroller, and the stroller rolled my purse and the diaper bag.  This worked out okay, except we always had to remember to remove any bags off the stroller handles before taking the baby out of it, or it fell backwards (travel strollers = lightweight strollers).  Despite knowing this, it still happened a bunch of times.  Super annoying.  

The JetBlue terminal is incredible and even has a kiddie play area.  We arrived to the airport early and let our daughter play as much as possible to tire her out.  

Hawaii – The longer stay plus business attire required meant we were packing the big suitcases and checking them.  Since our daughter had her own seat, she was allowed two carry-on items to herself, on top of her stroller and car seat.  Because my husband is a grown up boy scout, our carry on bags went like this:

  • Me – large purse plus bag of food
  • Him – backpack plus bag of food
  • Baby – diaper bag plus bag of food

We intended to take our daughter’s (non-travel) stroller base plus infant car seat.  Unfortunately, she outgrew her infant car seat about a second before the trip.  We then had to use her behemoth of a toddler car seat, which was not compatible with any stroller.  Instead, we had to buy a car seat dolly contraption, where you attach the car seat and roll it (and your baby) around like a suitcase.  Plus, we had to contend with our (increasingly beat up) travel stroller.  So as a result, we were each carrying two bags, with one parent wheeling a car seat and the other parent wheeling a stroller, and the baby’s bags were on whichever of the wheeling contraptions was not holding the baby.  

Then, despite leaving early for the airport, all our flights were already boarding by the time we got to the gate.  This was a combination of getting unlucky with slow security lines, plus delays in both of our first flight segments.  

The Verdict – Get to the airport as early as you reasonably can. Check as many bags as you affordably can.  Really consider whether you absolutely need a stroller at your destination if you’re also traveling with a car seat/dolly mechanism.  In hindsight, I think we could have gotten away with not having one in Hawaii.  Also, while at the airport, have your toddler walk or play as much as possible.  Be sure to look for family restrooms, which a lot of airports have.  These are MUCH easier because then both of you can comfortably go in there, along with all of your bags.  Above all, know that some things are just out of your control.  


Florida –  Staying at my in-laws’ meant our daughter had her own room, complete with everything she could ever need or want, such as a crib and toys.  Another positive was having a kitchen stocked with healthy groceries and plenty of space for our daughter to toddle.  However, my husband and I were always worried our baby would have a rough night and wake up the entire household (fortunately, she didn’t).  

Hawaii –  We sort of lucked out here.  Everyone made reservations back in the summer, and because the group rate we were getting was so fantastic, the cancellation policy was pretty strict.  When someone needed to cancel their room at the last minute, they’d already paid for half of it.  We took over their reservation and paid for the remainder of their room, in addition to our own.  Then we set up the rooms as adjoining rooms through the hotel and used the extra room for our daughter.  This enabled us to set up a completely private sleeping area for her where we didn’t have to worry about waking her during naps or at night. We were able to use the bed as a changing station and her bathroom as a bottle staging/cleaning area.  Also, the conference was being held in a huge resort that was fully equipped with a baby pool and a baby gym that our daughter visited nearly every day.  As a result, there were always a lot of options, and all were within a reasonable walking (or toddling) distance.  

The Verdict –  If at a hotel, springing for an extra room (or suite/villa) makes for a much easier stay.  If you’re not tied to a specific hotel, then I would rent an apartment or house to get more space in the most economical way.

Dealing with Time Zones

Florida – No time zone change.  Easy peasy.  

Hawaii –  Five hour difference.  Our daughter adjusted the same way we did, which was waking up early (5am) the first two mornings and then at a more reasonable hour (6:30am) the rest of the trip.  The pro to this was seeing the Maui sunrise every morning.  The con was that breakfast didn’t open until 7am, and then all the East Coasters descended like locusts.  

The Verdict –  As you would expect, being on or close to your time zone is much easier.  


It IS so worth it.  It’s a lot more energy when traveling with a toddler, and people definitely gave us the side eye. Some even questioned our sanity given that she wouldn’t remember the trips.  Perhaps not, but I do believe those experiences remain somewhere within her, whether consciously or not.  Watching our daughter experience the waves of the ocean and loving new foods like mahi mahi and abalone were unforgettable moments. It was also special for my husband and me.  One of the greatest joys of parenthood is gaining a greater appreciation for things we might otherwise take for granted.  Also, NYC winters can be pretty brutal so it was incredible to be able to soak up some Vitamin D!  

Given a choice, we’d probably choose a vacation destination in the Caribbean or Eastern Mexico, which are within four hours by plane with little to no time difference.  We’d also probably keep our trip to five days max.  My husband and I were really excited to get back to our lives in New York after that point.  Our daughter practically leapt into daycare when we got back so I’m guessing if she could talk, she would agree.  We don’t always have a choice (and our next family trip is to San Diego, a six-hour flight with a three-hour time difference), but our child is super chill, and I’m not just saying this because I’m her mother.  She’s been traveling since she’s three months old. Thanks to experience, I’m confident everything will be fine (even if she did have one major meltdown in JFK when TSA took her bottle for testing, but come on TSA, are you serious?).  

If you decide to go for it, then my biggest piece of advice is to always remain calm.  The worst case is one tough day and then you’re in a beautiful place.  If all of this seems too daunting, then there’s nothing wrong with appreciating where you are.  In the words of Seth Godin: “Instead of wondering when your next vacation is, maybe you should set up a life you don’t need to escape from.”

Luckily, we have that too.

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