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Planning a Family Vacation with Small Children in 13 Unlucky Steps

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My family and I are preparing to travel across the country from Illinois to Oregon to visit friends. My mind has been occupied for days trying to manage all the details, double check the bookings, and make sure we don’t forget anything we can’t replace when we arrive, like the baby.

Suddenly the movie Home Alone doesn’t seem so outrageous.

Somewhere between packing the three giant suitcases my family now requires, doing all the laundry, cleaning the house, finding a dog sitter, and cleaning the aquarium, I began to wonder:

When did traveling get so complicated?

I remember when booking flights two weeks in advance was organized. I’d turn up at the airport with an hour to spare, carrying on a backpack, my purse and a magazine. I’d fly at whatever hour was the cheapest and figure I could sleep when I was dead.

Now it’s more like if I don’t get some sleep I’ll be dead tomorrow. How times have changed.

This is what planning a family vacation entails these days. There are thirteen unfortunate steps. If that’s not a bad omen, I don’t know what is.

1. Contacting friends and family to see who has the space to house four people. Even at our most compact we require two bedrooms and a crib, and that’s only if one of us doesn’t mind being kicked in the head by a three-year-old all night.

2. Agreeing on an arrival date. Of course immediately upon hanging up the phone someone will do something horribly disgusting on one of the rugs and I’ll completely forget the previously discussed date. I will then proceed to procrastinate booking a flight until two weeks before we’re meant to fly or our host reminds me of our impending visit, whichever comes last.

3. By then all the good flights are full. Since red-eye flights and flights with three or more layovers are no longer reasonable forms of travel, I have to recontact everyone involved and change to a later date. It’s actually amazing I ever get invited anywhere. My friends must really love me.

4. This time I only procrastinate until three weeks before we’re supposed to fly and manage to successfully book a nonstop flight.

5. Of course the plane leaves at 8:00am and our nearest big airport is three hours away. The prospect of waking up two small children at 3:00am just to shove them into the car and drive for three hours fills me with the kind of dread usually reserved for tight spaces, spiders, and my in-laws. So now I have to book a hotel near the airport for the night before

6. The fun doesn’t end there. We usually need to rent a car when we arrive because the only friends foolish enough to invite our chaos into their homes are other sleep deprived parents. Can anyone say minivan? Needless to say, getting a ride from the airport is usually out of the question.

7. Next, I have to call the airline and wait on hold for an hour listening to terrible elevator music so I can book the baby a lap ticket. Clearly we parents can’t be trusted to do this online. We require the assistance of an agent who can ask us for our child’s birthday and then misspell his name several times. That’s it. I’m fairly sure the three-year-old could input this information.

8. A few days before the trip my denial turns to blind panic.

How am I going to entertain a three-year-old and a one year old in an enclosed space for five hours?

Will my baby’s shriek from Hell interfere with the navigation instruments?

Should I bring bribes for the other passengers seated nearby?

9. Time to start packing. A family of four traveling for less than a week requires more luggage than I took with me to college when I was 18. Every possible need must be anticipated and every potentially disastrous outcome meticulously planned for and avoided. Then doubled. It’s not unlike preparing for the impending apocalypse.

10. I stuff an entire carry-on bag with snacks, books, toys and crayons. No matter how many times I travel with my children I never learn that this bag will sit in the overhead compartment the entire flight while the three-year-old demands to play games on my iPad and the baby chews on my phone. I should really stuff the bag with tiny bottles of booze and Benadryl.

11. Each child must have three outfits per day because inevitably someone will spill, fall in the mud, or throw up on themselves. Also, no matter what time of year we are traveling, if we plan for warm weather it will rain and if we bring long pants and jackets we’ll be hit with a heat wave. I’ve given up trying to predict the weather and just bring everything we own. Take that, Mother Nature.

12. When the day of our journey finally arrives, I will have to prepare and pack four entire meals because the baby will only eat three things, none of which will be available as take-away or in the minibar at the hotel. No room service for my little gourmet. Peanut butter and Jelly sandwiches are acceptable any time of the day, right?

13. By the time we actually pull out of the driveway, I’m exhausted. I vow that I’ll never again travel with the children. Sorry kids, it’s couple-retreats from here on out. The kids are yelling in the back seat, my husband is turned around backwards in his seat trying to work the DVD player in the ceiling of the car, and I’m searching for the nearest drive-through Starbucks.

Suddenly I’m overcome by a sinful thought: I need a vacation.

So who wants to plan it for me? Advice appreciated.

Mary Widdicks is a 30-year-old mother of two boys, two male dogs, and an ever­ changing number of gender-­indeteriminate fish. Her husband calls her ‘Honey’, the three-year-old calls her ‘Mommy’, the baby calls her ‘Milk’, the dogs call her their Indentured Servant, and she’s pretty sure the fish have no idea who she is at all. She is also the writer of the humorous parenting blog You can also find her on Twitter.

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