7 Tips for Traveling with a Toddler

Not long after I had my son, Saxon, my fellow mom friends encouraged me to travel with him, insisting that babies are “easy” to take on vacation since they’re tiny and immobile. I thought this was the worst idea I’d ever heard. How would I manage to fly with an infant when I could barely get through a trip to the grocery store with him?

By the time he was 6 months old, we had made two family road trips and both times, the planning, packing and onsite logistics left me so exhausted and stressed out I vowed not to take him out of our zip code again until he could speak in full sentences.

And yet, I couldn’t help but wonder if I was missing out on some kind of magical parenting experience. After all, my Instagram was filled with adorable #travelwithbaby photos that made it look so easy and fun. Plus, I’m a sucker for matching father-son swimsuits. I decided it was time to take our first family vacation.

If I’ve learned anything as a mom, it’s that the first time doing anything with your child is always the hardest. To prepare myself for our five-day vacation, I read travel blogs, consulted Facebook mom groups and asked my friends with kids for their advice.

Here are the seven tips that helped me the most.

Andrea Lavinthal’s son Saxon

1. Manage your expectations. As any parent will tell you, it’s not a vacation if your kids are with you. It’s a trip where you still have to wipe someone else’s nose, enforce a nap schedule and keep your kid from sticking his finger in every electric socket. So if you pictured yourself sipping a glass of rosé and reading a book while your little angel quietly builds a sand castle next to your chair, let go of that lovely image. None of that will happen. Well, except for the wine. A little day drinking goes a long way on any family “vacation.”

Andrea Lavinthal’s son Saxon

2. Choose a family-friendly hotel. This may seem obvious, but there’s a big difference between a hotel with chicken fingers on the lunch menu and one that goes out of its way to cater to families. We chose the Kimpton Seafire Resort + Spa in Grand Cayman because of its convenient location (it’s a three-and-a-half-hour direct flight from where we live and the hotel is less than 30 minutes from the Grand Cayman airport) and the list of amenities for kids.

Andrea Lavinthal and son Saxon

In addition to the ocean, which is bathwater warm and practically wave-free, there’s a huge pool, plus a baby pool. They also offer a free day camp for kids over 5, a stellar babysitting service (more on that later) and lots of space for running around. But the best perk is that kids under 5 eat for free. Yes, free.

Andrea Lavinthal’s son Saxon

3. Pack like a travel pro. Whether I’m going away for one night or 10, packing always presents a huge challenge. So you can imagine how stressed out I was about packing not just for myself, but also for Saxon.

I’m not exaggerating when I say that I started a month out. First, I downloaded three different packing lists I found by Googling, “What do you pack for vacation with a toddler?” to make sure I didn’t forget anything important (white-noise machine, favorite stuffed animal, swim diapers, etc.).

Andrea Lavinthal’s suitcase

Then, I watched a tutorial by Hitha Palepu who wrote the book on packing. Literally — her book is called How to Pack. I messaged her on Instagram and she kindly coached me through the process, starting with my suitcase situation. I was planning for the three of us to share two checked bags and each have our own carry-on, but she convinced me to do three checked bags instead.

Her reasoning: You should always over pack for your kid — an extra outfit for every two days on top of their daily outfits. Plus, it keeps everyone’s stuff streamlined at your destination. Another bonus to checking the luggage is that it allowed us to go hands-free in the airport (we each wore a backpack stuffed with in-flight necessities), which is key when you’re chasing after a toddler.

4. Create the perfect carry-on. Speaking of in-flight necessities, I learned that there are a few things you should always have on the plane with you. The most important is a travel-size first-aid kit stocked with any prescription medications your child needs, over-the-counter medications (I did Tylenol, Advil and Benadryl), Band-Aids, Neosporin and a thermometer.

The second is enough snacks to fill an aisle at Costco. (That’s just a slight exaggeration because you can never have too many Cheddar Bunnies.) And the last is an extra change of clothes for your child and for yourself because imagine having to sit for hours in a T-shirt covered in vomit or worse.

Andrea Lavinthal’s suitcase

5. Splurge on your room. Pre-baby, my boyfriend and I would spend the majority of our beach vacations outside, coming back to the room only to shower and sleep. Post-baby, we found ourselves on day one of our trip sitting inside during prime beach hours, texting each other so we wouldn’t wake the baby while he took his afternoon nap just a few feet away. (I was not blessed with a child who will sleep outside in the stroller under a shady tree.)

On day two of our trip, I upgraded us to a larger room with a separate living-room area, a big balcony and a giant walk’in closet where we put the Pack ‘n Play. It cost more than we’d planned to spend, but it was worth being able to read a book outside and flush the toilet without worrying about waking up Saxon.

Andrea Lavinthal’s son Saxon

6. Use the babysitting service. As I mentioned, the Kimpton Seafire has childcare programs including an in-room nanny. This was key for us since we wanted to have a couple of dinners without the baby (mostly so we could eat later than 6 p.m. and drink our margaritas in peace).

At first, I was hesitant about leaving him with a stranger, until the hotel informed me that all their childcare professionals are required to have over three years of direct experience caring for children and they must be trained in CPR and first aid. They selected our sitter, Althea, specifically because she works at a children’s enrichment center that specializes in toddler and infants, and she was even more wonderful in person than she was on paper.

We made a reservation at one of the hotel’s restaurants so we were nearby (just in case) and she texted me throughout dinner to assure me that everything was fine. We felt so comfortable with her that we used her for a few hours during the day so we could hit the spa, and two more nights so we could have dinner off property.

It’s also worth mentioning that the entire staff — from the housekeepers and servers to the concierge and front-desk team — went out of their way to look after Saxon during our stay. If your hotel doesn’t offer childcare, e-mail the concierge before your trip for the name of a local service, or ask your fellow moms on Facebook if they’ve used someone that they recommend. Just try not to spend your precious baby-free hours talking about the baby.

Andrea Lavinthal and son Saxon

Andrea Lavinthal and son Saxon

7. Have fun. Between all of the planning, packing and pre-dawn wake-ups, I almost forgot that we were on vacation. It’s hard not to freak out about every little thing, but you really have to relax and go with the flow. Your kid is going to have fun no matter what, so you should too. And like all things with parenting, you’ll eventually forget how stressful traveling with a toddler is and just remember the look on his face the first time he went in the ocean.

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