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How to turn around a terrible vacation

You’ve spent months picking the ideal destination. Researching the best place to stay. Figuring out what you’ll eat, where you’ll swim, and the perfect outfits for doing it all. This is the trip of your dreams… until it isn’t. Here’s how to turn around a terrible vacation.

The Issue: The other family you are traveling with is making you miserable.

There’s nothing quite like travel to bring people together. Then again, there’s nothing quite like travel to have you questioning why you even became friends with these people in the first place.

Next steps:

First of all, breathe. There is this myth that travel is something everyone inherently loves. While travel is fun, it is also incredibly stressful. We’re tired, we’re out of our routine, and if you’re with kids, everything from meals to bedtime is 100 times harder. Give yourself some grace. Give your travel companions some grace. Your trip isn’t going to be Instagram perfect, and that doesn’t mean it’s a total failure.

The best thing you can do is discuss the big points of stress before you leave. These are typically money, space, and schedules (if you haven’t discussed prior, I say better to do it late than never).

  • Are you going to split everything, or is each family on their own? If you have any inkling money might be an issue, talk about it before you leave.
  • Book separate hotel rooms, and if you’re sharing a house, make sure there enough bedrooms and bathrooms. It’s so important for people to have their own space for when they need a break.
  • If your kid needs a nap every day at 1pm or else he turns into a gremlin, make it known (and don’t expect everyone to cater their vacation around your child’s needs).

How to rewrite the narrative:

You are not handcuffed to this other family. If you need a respite, just make plans with just your own family for the day. And if you have to, I say blame your kids. This is a scenario where a little white lie may be just the ticket. “Little Sally is really craving some time with mommy and daddy, so we’re going to take her mini-golfing and out to dinner by ourselves. Let’s all have breakfast together tomorrow morning!” No one can really argue with you wanting to make the best choice for your kid. And hey, if they do, you never have to travel with these people again!

The issue: You booked a cottage right on the beach and it’s poured the whole time.

bad vacation

You’ve dreamt of your summer beach vacation for months. Drinking your coffee in morning sunshine as the kids frolic in the waves. Romantic walks on the beach with your sweetie. And then, it rains. Every. Single. Day.

Next steps:

Aside from going home, there’s not much you can do. After your completely deserved 15-minute pity party, move on to the next step.

How to re-write the narrative:

You’re no longer on a beach vacation, you’re on a mission.

  • Haven’t you always wanted to make a pie from scratch, or craft one of those desserts you’ve never heard of from the Great British Baking Show? Now is the time.
  • Somebody needs to figure out who makes the best donut/beer/pizza in the area, so why not you? Seek out little gems. Enjoy the drives in between. Compare. Contrast. Discuss.
  • Get crafty. Buy art supplies and paint the rainy view from your window. Show your kid how to make an old-school friendship bracelet. Cut up some magazines to make the vision board that’s been on your to-do list for months. Part of the fun is exploring the local hardware or craft store for ideas.
  • Teach your kids a game you’d never have the patience for at home. Monopoly? Cribbage? Rummy?
  • Visit indoor destinations like museums, historic sites and aquariums. Of course everyone has this idea, so go right when they open or an hour before close to beat the crowds.
  • Get out and enjoy the “bad” weather. Hike in the rain, get dirty on the beach, splash in the puddles, enjoy outdoor destinations without the crowds. So long as it’s safe outside, the right gear makes any weather tolerable. If you packed all wrong, suck it up and buy the right footwear and jacket. You’ve already sunk time and money into this trip, what’s a few more bucks to make it significantly more fun? You can often find amazing gear at thrift stores! Who cares if it’s stylish, you just need something to work for a few days.

The Issue: The rental cottage you booked is the pits.

bad vacation

Everyone’s worst nightmare: the adorable cottage you booked looks (and smells) more like the set of a 70s horror movie than a quaint summer vacation rental. 

Next steps:

Nip this one in the bud right away. If you’re booking directly from the owner, give them a chance to right the wrong. If the place isn’t clean or is missing something specifically stated in the listing, ask them to fix it. There are a lot of people who use a third party to manage the property, and the owner may not even be aware of the situation.

It’s best to become familiar with cancelation policies before even booking, but better late than never. Re-read the fine print. Many vacation rental companies will work with you if the property does not meet expectations, provided you contact them within the first 24 hours. Additionally, if you leave early, you may be able to get money back for the nights not used.

If the experience is truly disastrous (for example, you can’t get into the place nor connect with the rental company), contact your credit card company to withhold payment.

How to rewrite the narrative:

Get real with yourself. Is the problem something you can live with, or will it truly put a damper on your entire experience? If it’s the first, change your attitude. It’s easy to obsess and complain when expectations aren’t met, but let’s not allow disappointment ruin your trip.

If you can’t live with the accommodations, figure out a plan B. Maybe your rental cottage vacation will morph into a resort stay in nearby town. Sometimes it’s better to be a bit inconvenienced and lose a little money if it means the overall experience will be better.

The issue: The airline lost your luggage.

Oh boy: nothing worse than that sinking feeling of still standing at the carousel, but all the bags have been claimed. It’s estimated that less than 3% of baggage get mishandled, and that includes stolen, damaged and delayed luggage, so your chances of it being totally lost are slim. The good news is it’s usually just delayed and will show up (and like be delivered to you) in the next 24 hours.

Next steps:

You’ll have to file a claim for the luggage, which is done at the airport. Be sure to get the phone number for the airline’s lost luggage department. Save receipts for any items you may have purchased while your luggage had its own little adventure. Toothbrushes, toothpaste, deodorant, underwear—the airline will likely reimburse you for items within reason. Needed an Hermes scarf to get you through the night? The airline will likely disagree.

If the airline completely loses your luggage, it’s a whole different can of worms. I’ll be honest: airlines don’t make it that easy to file a claim. You can’t just say there was about $1,000 worth of stuff in there, they will want a list of every little thing you’d like to get reimbursed for—from jeans and shoes to individual makeup items. This is why it’s great to have a packing list, or snap a photo of what’s in your bag. Domestic flights may reimburse up to $3,400 per ticket; international up to about $1,600. But this is a situation where the squeaky wheel gets the grease. You’ll likely need to be persistent, and maybe little annoying.

It’s worth noting that your credit card company might actually go to bat for you here! Many credit card companies offer travel insurance or assistance with recovering lost luggage when you’ve purchased the trip with their card.

How to rewrite the narrative:

I know a family who traveled to Europe for 10 days, baby in tow, whose luggage never arrived. It was stressful for the first day, but they ended up buying a few clothing items and toiletries to make it through the trip. By the end of the vacation, they were blown away at how little they actually needed. We tend to pack for every scenario, but in reality, you might just learn that a pair of jeans, clean undies, a couple tee shirts, a jacket (and maybe a little mascara) is all you really needed in the first place.

The Issue: Your flight gets cancelled.

You’re stranded at the airport and not sure how you’ll get to your destination (or worse, back home).

Next steps: Read this.

And no matter how your terrible trip turns out, remember to notice the details.

From your friend’s annoying helicopter parenting to the raccoon who made themself at home in your AirBnB, it’s those little nuggets that will one day have you laughing, not crying, about this awful experience.

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You’ve spent months picking the ideal destination. Researching the best place to stay. Figuring out what you’ll eat, where you’ll swim, and the perfect outfits for doing it all. This is the trip of your dreams… until it isn’t. Here’s how to turn around a terrible vacation.

This Post Has 7 Comments

  1. Excellent article! Great suggestions. We packed for a trip to Europe where we were LOL sure the weather would be good. It was not. I took my low-cut shirts and put them on backwards for warm. All my pictures have me in the same coat. I just did fun different poses. Gene Kelly singing in the rain, etc. One night I got up to dance in the lounge in a lineup of people doing the Macarena. Unbeknownst to me the front zipper of my beach cover-up which I had turned into my dress over my leggings, came unzipped. I should have become devastated and disappeared. I decided to change it up. I laughed, made the most of it, and might have been the hit of the lineup! And the difficult weird people on the trip? They became the source of a lot of laughter later on when we got home. Thanks for your article!

  2. Brilliant. Great ideas and thanks so much for the details. I’ve already forwarded this to a traveling partner. ATTITUDE – and keeping it smiley. Taking pictures, keeping a list of what is inside my suitcase. Wow. VERY good advice, all!

  3. We just returned from an epic international trip on which we flew around the world traveling through all time zones & had several issues from delayed luggage (thank goodness we packed two days of clothing in our carry ons),not up to par Airbnb, to train delays, the worst of which had us arriving back to our flat at 3 am. It makes things memorable for sure but I’d rather remember it for the good experiences & beautiful sights

  4. Sometimes when a travel experience does not meet my expectations, I consider another perspective. Perhaps the purpose of my trip was not to meet my expectations but to help someone else meet theirs. When you approach it that way, don’t be surprised if one or more people seek you out as the adventure is winding down to let you know that your presence in their lives, during that short moment in time, made all the difference in the world to them.

    1. What a wonderful unselfish comment! So refreshing in today’s world. Thank you. Could I possibly post it without your name!

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