How to Plan a Family Vacation: Struggles of a Single Working Mom [personal story]

This article was written by Alvina Emmy from

I miss the days when holidays used to be all fun and relaxing. I could get sloshed at 10 A.M in the morning without inviting dead cold stares from anyone. Things changed when I got married. Holidays post-marriage and kids meant quietly sipping tequila sunrise by the beach while watching my husband miserably failing at surfing.

Things took an unexpected turn when William died two years after our marriage after a massive stroke. I was pregnant at that time with twins. Life hasn’t been easy since then but I manage.

Cut to the present, I am a working single parent. I get only two vacations a year, one around Christmas and one in the summer. The image of a lone parent with her kids doesn’t really fit the conventional image of a fun family holiday. I get it.

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Secret Holiday Goals

If I am being really honest, I don’t feel like going on a picnic with my in-laws (here’s hoping they don’t read this) and constantly keep an eye on my twins who seem to be running in every possible direction. I just wish I could throw myself on the couch, have a slug of hot chocolate while reading the book I’ve been dying to read since forever.

But my kids, mother, brother, and sister-in-laws are totally psyched about summer holidays by the beach or the snowy mountains. I have to admit that my mother-in-law is always at my beck and call. But I feel really bad for having to call her to fly over to my home frequently to watch over the kids.

At the end of the day, my twins, their whims, diaper blowouts, sickness, midnight mood swings, and general lack of cooperation are solely my responsibilities.

Holiday Planning Feels Like a Chore At Times

Don’t get me wrong, I am just as excited about family holidays as anyone else. But you see, taking care of two kids away from home is tough, even for two parents. These days, holiday planning feels like a full-time job for me.

My mind would begin to unravel two weeks before the D-day. Did I include everything in the checklist? Do I need to bring two extra pairs of socks? Am I carrying enough medicines with me? What is the reasonable volume of nappies for a week-long trip for two 5-year-olds?

Oh! The sweet punch of chaos and confusion in the gut.

And it’s not like I don’t have a job, errands to run or kids to pick up from the school. My mother-in-law would come over a week before to help me out but it’s still a lot of work. It’s all so chaotic and I want to scream so bad yet I don’t (at least not anymore).

I keep thinking about the possible nightmare scenarios I might run into during the trip.

The Unbearable Sympathy

When regular people imagine family holidays, they picture happy couples holding hands together, walking by the serene beach, going all mushy while their kids are engrossed in building sandcastles.

No wonder single parents like me get a lot of “oh! I’m so sorry for your loss”, “this must be really hard for you” with a sympathetic head tilt. Don’t get me wrong. I appreciate the sentiments but losing my husband was one of the most traumatic things I ever had to deal with. I would love not to be reminded of it when all I’m trying to do is look past is and have a good time with my family.

The Packing Hysteria

As if the thought of constant head bobbing sympathy wasn’t annoying enough, now I have to start packing for two kids. How do I ensure that I’m packing enough without overloading the luggage? Quite a thinker, isn’t it?

The sheer volume of diapers I have to carry alone makes me want to cry. There is an entire section in my luggage only dedicated to diaper and diaper-related items to deal with poop emergencies. The cherry on the cake would be the extra weight of the tons of warm clothes I’ve to carry if we are traveling to a cold climate place.

The Couch Potato Syndrome

I am a child of the late 80s, a time when addiction to technology was the least of any parent’s worries. Spending holidays sitting on a couch with eyes glued on a ridiculously large smartphone screen feels like an abomination to me.

I absolutely hate it when my kids insist on staying in the hotel room with their iPads instead of playing outside.

Imagine it’s Christmas, the NYC is wrapped in the snowy blanket and the city smells of butter, cocoa, and happiness. Instead of smashing snowballs on each other, my kids get their kick from a virtual Hot Wheels race! I can’t even.

TIP: Check out these 20+ Travel Toys for Toddlers that are easy to pack and will give them some good old screen-free time!

My Kids Hate Walking

You might think that once you manage to get their lazy tushies out of their virtual world, the rest is a cakewalk. Well, guess what? It’s not? My kids, just like every other kid, would refuse to walk sooner than you anticipate. However, I don’t totally blame them for that (I’m not an evil mom!).

Their tiny little feet can obviously get sore after walking for 2-3 hours straight. Since lifting and carrying two 5-year-olds is not a logical option for me or for anyone, I bring along a double umbrella stroller for travel purposes.

My kids love it and I think it’s a must-have travel gear if you are traveling with kids. The twins can take a nap on it whenever they want to while I can use it to store my travel bag, bottles, and snacks during sightseeing. It helps my kids stay protected from the UV rays and heat as well which makes carrying this bulky thing all the way from New York totally worth it.

Sleep? What Sleep?

how to get your kid(s) to sleep on vacation

It’s a no-brainer that traveling wreaks havoc on the sleep schedule. At the end of the day, after all the sightseeing, walking in the park, swimming, and endless selfie clicking, all I want is some alone time. That’s not going to happen unless I put my kids to sleep which seems like an impossible task.

I can understand that falling asleep in an unfamiliar environment can be difficult for anyone. To make them feel more at home, I bring along their favorite stuff toys and the blanket they use back at home with me. But that hasn’t been of much use so far. I am hoping that this problem will go away when they grow up a little more and get used to traveling.

TIP: Take a look at this article if you’re wondering how you can get your kid to sleep while on vacation.

Food Hygiene Is a Joke

Upset stomach and horrible acid reflux are the last things I want to deal with on a holiday. While I’m not a quintessential modern mom who forces their children to survive on a diet of kale and stuff, I also don’t advocate junk food diet.

Making kids eat healthy on a vacation is an impossible task even for Iron Man. Most hotels have “if you eat this, you get a free that” offers during holidays. What a brilliant way to make kids stuff their tiny bellies with loads of crap!

But hey! No matter how hard it gets, I don’t give up. I try my best to establish a few ground rules before we set out. My little chipmunks know that if they don’t finish their veggies, they won’t get to have the dessert for. They should know that I mean business.

To make my work a bit easier, I have been lately making conscious efforts to follow a healthy eating habit at home. After all, all good habits begin at home, right?

Since kids are picky eaters by default, I have also started getting their palates used to the local cuisine of our upcoming holiday destination one year prior to the trip. I just don’t want my babies to live on stupid pb & j, canned crap, cookies and candy bars instead of enjoying authentical local food.

Disease Monsters

Sunburn, skin infection, flu, colds, bruises, alien attack- the possibilities are truly endless when you are on a family trip with kids. The very thought of them falling sick in an unfamiliar city scares the bejesus out of me.

My mother-in-law is very old school in these matters. She belongs to that school of thought which believes that essential oils are the real deal. And her go-to remedy for toothache is brandy! Look, I simply adore that lady but not her home remedies.

So I always make sure to carry a bunch of essential meds like ibuprofen, antihistamine, antibiotics, teething gel, skin ointments for rashes and itching, sunscreen along with a first-aid box. Jason, the older one, has asthma. Hence, I make sure to keep one inhaler in my carry-on bag and another one in the checked-in baggage for safety.

The Dark Side of the Moon

My kids are not particularly good at expressing their emotions, even though they are just kids. But when they see other children having fun with their dads, I look at their faces and it breaks my heart. I and my mother-in-law do our best but no amount of effort can ever fill the void, you know?

I don’t mind taking care of two kids on my own, they complete me, they are my whole world. Having said all, it would have been really nice if I could watch them laugh and grow and annoy the heck out of me with my husband by my side.

boy playing on his own in the sand

Ending on a High Note

Enough of the emotional talk. I don’t want you to leave this page with a sad-face and a heavy heart. My kids will never stop missing their father and I will never stop feeling incomplete without my life partner. But that is not the end of the world for us. I’m grateful for what I have.

 Even though I crib about the whole packing conundrum and not getting time to myself, deep down inside, I love it. I love the chaos, I love the possibility of exploring a new place, new people and most of all, I love spending quality time with my kids. So family holiday rocks even though I suck at planning it.

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