Overcoming the Unexpected in Travel

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There are so many lessons I try to teach my boys when we travel. Some have to do with travel itself (always carry the essentials with you; stick to drinking water on flying days, and don’t ever be afraid to ask for directions or help). Others have more to do with patience, tolerance, and making the best of every day, especially days of travel. Life can be hard enough without us contributing to it. Travel can be stressful enough without us contributing to it. As a mother and wife, I have had my share of stress, meltdowns, and moments of complete overflow of emotions. And that’s all just coming from me. When it comes to dealing with my kids, or even my husband’s own personalities and “special” moments, it can sometimes be too much to bear.

Like when we aimed for a staycation in the city after a long week of work and homeschooling. We made our hotel reservations, packed our bags, took the train into the city and made all sorts of plans.

From the moment we arrived to our hotel the rain started and didn’t stop the entire weekend long. At first I was disappointed that we had spent the time and money on a weekend I would have preferred to be home in my pajamas and with a book in hand. The kids were sad that we might not get to do half the fun stuff they were looking forward to.

Rainy day in NYC Rainy day in NYC

Everything was soaking wet and the rain just wouldn’t let up.

But instead of staying inside or canceling the trip altogether and going back home, we took on the city, in the rain and though our plans changed a bit, we were reminded of how much fun we have together and how much we enjoyed just being together.

Rainy day in NYC

There were brief moments of breaks from the pouring rain and we would slow down our pace to take in the reasons why we choose to spend our free time here.

Rainy day in NYC

We took breaks from the weather in shops and food markets, which often lead to discoveries of new eateries that we hadn’t tried before.

Rainy day in NYC

We got to enjoy favorites that we rarely stop into because the lines are often out the door, but the rain kept the crowds and we feasted!

Sure we got wet, our shoes were ruined, and we looked a total mess the whole time, but we had such a fun weekend and laughed and talked and just really enjoyed our time.

Rainy day in NYC

As we walked around, I remembered how pretty I think the city looks when it rains.

We can’t always see the bright side of things immediately, sometimes the circumstances never lead to a silver lining, but I have learned over the years that if we give things a chance, something positive will eventually show itself.

Rainy day in NYC Rainy day in NYC Rainy day in NYC

We especially loved walking the city at night, when the rain ceased for a bit.


Tips for overcoming the unexpected

  • Have a back up plan: if you planned to be outdoors, what indoor options are there to replace them and vice versa. Is there anything else you would rather do if your favorite attraction is closed, etc.
  • Set aside a small budget. We ended up taking more taxis than we planned (our initial plan was to walk everywhere). Just the little buffer in your budget can help soften the blow for having to change plans around and maybe taking on an additional expense.
  • Travel insurance is great, but may not always cover “canceling a trip due to rain”. Check out the cancellation policies for any bookings ahead of time if you do have to make that decision. Hotels are usually pretty lenient as long as they are not same day cancellations.
  • Don’t sweat the small stuff. I am not a pro at this, I will admit. It is always a work in progress, but it gets easier with time. When you feel yourself getting in your own head over things, try to focus on the bigger picture and the reason you took that trip in the first place.

As we look towards the last weeks of summer and plan to head out on those last-minute family vacations or weekend getaways before school starts, just remember: things may not go exactly how you planned them to, but that doesn’t mean the moment is ruined. Sometimes the best memories are hidden in the unexpected.

Happy last days of summer, and most of all, happy travels!


In partnership with Embassy Suites. All opinions are my own. Find more travel tips from experts and other parents by visiting embassytravelhacks.hilton.com or follow the conversation on Twitter and Instagram using #prettygreat.


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Carol Cain

Carol is her happiest when on an adventure, either close to home or farther away. She's the mom to three fun boys and wife to a handsome Irish/Scot. She lives in New Jersey with her happy crew, but will always be a girl from Brooklyn. You can read her full profile here.

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2 Responses to Overcoming the Unexpected in Travel

  1. Gessell says:

    That’s awesome how you were able to have fun even though the weather sucked. One of the things with traveling is certainly being flexible with plans. I for one used to try to plan out everything in advance and used to get upset when plans went awry. But that all changed once I started traveling with my baby.

    • caincarol says:

      Thanks! Yes, kids have a way of changing how you travel for the better. I have definitely become more easy-going with itineraries since becoming a mom!

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