Someone Else’s Family Vacation

In my humble opinion, the only acceptable answer to “do you want to go to Hawaii?” is a resounding “YES”. Possibly even a “HELLS YEAH” if you’re feeling particularly raucous. In any case, an offer to journey to a tropical island paradise should never be met with anything but enthusiasm – especially if you’re a nanny. Which is why, when my bosses asked me to go with them to Hawaii, I had nothing but enthusiasm for the idea. It ended up being one of the most memorable and incredible experiences of my life, but it was not at all the easybreezycovergirl Hawaiian vacation I was expecting.

Depending on your level of familiarity with the nanny-verse, you may or may not know that some families ask their nanny to accompany them on vacations. Despite my extensive research on the career before throwing myself into it (and by research, I mean watching several Julie Andrews movies), I had no clue that this actually happened in real life. I had no idea that taking a nanny on vacation was a luxury available to anyone other than the one-percenters, but evidently, it is.

When the C’s (my boss-family) first asked me to travel with them, I was thinking we would take a road trip to a theme park or something similarly run-of-the-mill. When they dropped the bomb that Hawaii was their destination of choice, I had to politely excuse myself to scream and do a happy dance. To me, going to Hawaii was about as likely as going to the Moon – something a select few very lucky individuals do, but far beyond the realm of my possibilities. I consider myself lucky if I get to go to the Olive Garden more than once a year. Yet here they were, offering me this chance to see an incredible place with my favorite little dude at my side – a win-win.

In the weeks leading up to our departure, I spent every available moment scouring the Internet for tips on traveling with toddlers and suggestions for nannies vacationing with families. I read every possible article in the hopes that I could somehow prepare myself for something this huge. Let me be blunt here – there’s no possible way to prepare yourself for this. Traveling with a toddler is a challenge in and of itself. The challenge increases exponentially when you add the long flights, the unfamiliar situation, and the politics of working through someone else’s family vacation.

To be honest, I was sort of expecting the trip to be an easy way to enjoy a vacation on someone else’s dime. I was sorely mistaken. Don’t get me wrong, I did enjoy every minute of it (and I paid for very little – thanks, Mr. and Mrs. C!), but it was by no means easy. Working during someone else’s vacation is such a challenge, no matter how wonderful they are or how well you get along with them. It’s hard to know where you stand in that situation if you’ve never been there before, and none of us ever had.

I never knew if I was supposed to tend to Bug (the little dude, about 15 months old at the time of the trip) if the C’s were present, or if I should let them take over. Bug was also sleeping in my room, so I didn’t know how to handle it when he got fussy. I always felt guilty when Mrs. C would get up and come grab him after hearing him cry for a little while, despite my attempts to comfort him. When he went to bed, I never knew what my role became – could I go socialize with the C’s and their friends on the lanai? Was it okay for me to accept a glass of wine with everyone else? Could I joke with them? There were so many potentially awkward situations throughout the experience, and finding my place in their family vacation felt exhausting at times.

On top of that, I didn’t have much free time, unless you count Bug’s naps (and even then I couldn’t leave the condo). Most nights the C’s would go out with their friends who had traveled with us, or with their parents who met us there, leaving me alone with Bug. When we did go places, Mrs. C and I shared the job of entertaining Bug and keeping him occupied. I ended up working much longer hours than I do regularly, and I was pretty exhausted when we finally made it home.

The trip was still one of the most incredible experiences of my life. Once I adjusted my expectations and found my place in the picture, I had an amazing time. Sure, I was working, but I was working in Hawaii. Bug still had fits and my job still brought difficulties, but they happened in Hawaii. And best of all, I was able to witness my favorite little dude as he experienced so many things for the first time.

I got to hold his hand while he grabbed his first fistful of sand. He sat on my lap while we watched whales breach right next to the shore. I held him in my arms while the sounds of the gorgeous Pacific Ocean lulled him to sleep on our first night there. I identified each new plant and animal that he excitedly discovered. I filled a box with the plumeria blossoms he brought me every day, a box I will never get rid of (even now as the blossoms are years old and nothing but a pile of dust). Being in Hawaii was incredible, but it was nothing compared to witnessing Bug in Hawaii. For that more than anything else, the trip will always be one of my most cherished memories.

Being a nanny is hard sometimes. We work crazy hours. We face extremely high expectations and standards. We never know if we’re friend or employee, so we never really know where we stand. That being said, there are so many things that make being a nanny worthwhile. The love and connection with each charge in our care, getting to experience incredible new things, and witnessing the kiddos who become our best friends have some of the best days of their lives, to name a few. Being a nanny is hard sometimes, but it’s still the greatest job in the world.

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