Take It From Me: How to Stay Sane on a Family Vacation

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Deal Expert, Chicago
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As parents, we’ve all had this thought, “I’m going to need another vacation after this one because my family is stressing me out!!” It’s okay, you can admit it. We’ve all been there. I just came back from a family vacation to Boston with my wife, 4-year-old and baby and though we had a great time, that same thought scampered across my brain a time or two.

With that in mind, pun intended, I have collected a series of tips that can help you stay sane on your next vacation.

Before you go

Plan with, not despite, your kids. A few months before we left, I asked our older son, “What would you want to do on vacation this year?” He said, “I want to ride trains and visit museums.” Fair enough. Why take him to a Caribbean beach vacation and him bored or frustrated?

From there, my wife and I narrowed down our destinations to train- and museum-friendly destinations. Boston, New York, D.C. and San Francisco all made the list. It was pretty comparable to what the IOC does when selecting the next Olympic site. We eventually narrowed it down to the Boston and D.C. bids before opting for Boston (Mommy went to school in Boston so that carried more weight with the judges — typical scandal).

From there, I grabbed a bunch of Boston guide books from our local library and brought them home. I leafed through them, pulling out stops and attractions that might appeal to us, getting our son’s thoughts along the way.

Finally, the voting. Since our 4-year-old can’t read yet, I drew pictures of each attraction and activity on notecards. I asked him to put the cards in order, ranking what he wanted to see the most, second-most, all the way down to the least important attraction we could miss without a tantrum. Once he did that, I took photos of his notecards and arranged our itinerary for the trip accordingly, plotting out plenty of time at the high-ranking stops and shoving the less important places to the back of the trip. Throughout the trip, I looked at those photos on my phone, confirming that we were hitting all the highlights.

Make a “Mad List.” For some reason, my wife and I have left our cosmetics bag in the bathroom by accident during our last few vacations. Upon arrival, we got upset at ourselves and then had to hunt down a Target, buy toothbrushes, toothpaste, the works. So, this time around, we made what we called our “Mad List,” meaning “I will be mad if we forget to bring this.” We made the Mad List, checked items off as we packed and didn’t actually forget anything this time.

The plane

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Ah, the dreaded plane ride. We’ve all been the family on the plane with the screaming kid or the empathetic parent watching someone else’s child meltdown. But there are some steps you can take.

Pack your carry-on like you’re climbing Everest. If you’re going to emerge relatively unscathed, you’ll need all the right provisions: water, juice, puffs, baby food, spoons, napkins, bibs, books, toys, granola bars, fruit snacks. I once saw two parents try to entertain a baby with the plane’s emergency evacuation manual for an entire flight. And while that pair of parents could take their show on Broadway, it quickly lost steam with their audience and the baby lost it for the duration of the flight. Bad preparation.

And don’t stow that carry-on above you in the overhead bins. It has to be within reach at a moment’s notice.

Skip the free drink. Everyone takes the free drink. I get the logic: I paid $800 for these plane tickets and if this airline is going to hand out something free, I WANT IT. But think this over: when was the last time you put an open container of water in front of your toddler in any setting? My pair of soaked pants and nearly drenched computer would argue that a secure bottle of water is worth the extra cost.

Ignore the eye rolls and dirty looks. A few years ago, when we took our first plane trip with our older son, I was anxious about the trip for weeks in advance. Then, during our actual trip, I dreaded the return trip home. It’s hard to enjoy your vacation when you’re constantly stressed about something in the future.

Four years later, on this trip our baby started crying for a few minutes on the plane ride to Boston. Instead of tensing up and worrying about the other passengers, we focused on our baby, helped him settle down and didn’t sweat it. On the way home, our boys were happy the whole way, but a family across the aisle was having the hardest time dealing with their crying 2-year-old. Yet, no one seemed to really notice. People have headphones and if they didn’t want to hear kids, they shouldn’t have flown coach.

On location

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Get up early: I know this sounds counter-intuitive, but getting up earlier than your kids actually gives you time to yourself. One morning, I got up at 6 a.m. and walked outside onto Copley Plaza. Sitting on that park bench, soaking in the peaceful silence of the morning was one of the highlights of my entire trip. It was serene. I knew that later in the day I’d be struggling with the stroller and dealing with potential tantrums, but so what? I had this time to myself.

From there, I went for a run in the neighborhood. Not only is this a terrific way to feel good about yourself, staying healthy even on vacation, but you can scout potential locations. I had no idea that our hotel was a mere three blocks from the Boston Public Garden. We could easily walk there. I even ran through the garden, scouting the “Make Way for Ducklings” statues (which was a lot harder than I imagined). Later in the day, we would visit that same garden and we would have all gotten into a fight, hunting endlessly for those ducks in the heat. No thanks. This way, I knew exactly where they were so we could make a beeline to the statues like a tactical plan out of “Zero Dark Thirty” (or in this case, “Zero Duck Thirty”).

Then, on the way home, I got to be a hero, picking up bagels and juice for my family as they woke up for the day. Everyone loves Daddy.

Don’t mess with bedtime. I know it’s tempting to make a bunch of plans at night – concerts, fireworks, the works. But how would your kids react to that same itinerary if you did that at home? Our baby gets tired and goes to sleep right around 6:00 or 6:30 every night at home. So, while I wanted us all to go to a concert at the Hatch Shell, that concert would have started at 8 p.m. I would never bring our baby to that at home and that would be pushing it for our older son too.

Instead, we wrapped up our day right around 5, had dinner somewhere and came back to the hotel to put our baby to sleep in the room. Even better, while my wife put the baby to sleep in the room, our 4-year-old and I played golf with his toy set right in front of our hotel in Copley Plaza. He loved it and when I got a text from my wife saying that our baby was asleep, I brought in our older son so he could take a bath and wind down for the night too.

I’m not saying you can’t or should never stay up late for a fireworks show or a special evening, but know the risks. Maybe you can sleep in the next morning and have a lazy day. But your kids might like the comfort and security of their bedtime routine, especially when they’re sleeping in a strange hotel room away from home.

After you come home

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Learn from your mistakes. A few nights into our Boston trip, our 4-year-old said to me, “Daddy, I miss our house. When are we going home?” This caught me by surprise and I panicked. We were going to be in Boston for seven more nights – there was going to be a whole lot more “missing our house” to come!

In the end, it wasn’t a huge deal, but I understand what I did wrong. In the past, we had taken more small road trips, where we usually stayed two nights. Eight nights in Boston might seem like eternity in comparison, even if you’re having a great time. I asked our little guy why he missed our house and he said, “I miss my room. I have like, 130 toys.”

So, next time I might think about planning a few mid-range vacations instead of one annual “big” vacation since that much time away might just be too much (at least at this age).

Compare your pre-trip plan to what you actually did. Did you hit everything on your list? Did you have a great play book that went out the window as soon as it was game time? For us, we probably packed in a bit too much on some days. On weekends at home, we’ve learned that we can safely plan one “event” a day without a problem – a birthday party, museum visit, family dinner, you name it. Once we notch that number up to two, things get dicey.

Grown-ups and kids get tired, get sick of their car seats, get hungry and meltdowns ensue. We know this about ourselves. But in Boston, we were so excited to do everything that we just kept going, even though our pre-trip plan called for one “event” a day just like home. One day, we went to a museum and extended our stay to visit the North End for a homemade Italian dinner. After the museum, the boys were tired and we were all ready for a quiet night in the hotel’s neighborhood, but Mommy and Daddy knew we wouldn’t be able to visit the North End again if we didn’t push it that night.

So, I wouldn’t say we regret that evening, but we weren’t surprised when a stressful dinner followed (crying, timeouts, tantrums — and that was just the parents). Maybe next time we’ll just have to save some things for our next trip and have a more leisurely itinerary. Better to have a relaxing vacation than a stressful one, right?

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