What To Do When Everything On Your Trip Goes Wrong

Let’s be real -- no vacation is even close to as perfect as it seems on Instagram. More often than not something goes wrong - among other things, planes get delayed, it rains the entire time, and you don't actually get the Louvre all to yourself.  I've had more than my fair share of vacation mishaps, which most recently included arriving at my airbnb only to find that there was no running water.  

Although these situations are far from ideal, a few simply tips can turn them from trip-ruiners to simple speed bumps on an otherwise delightful vacation.  First, stay calm - stressing out just ruins the trip for everyone, and there’s usually a simple solution for most travel nuisances.  Second and most importantly, be sure to have a contingency plan before you travel, and use it to adjust your plans as needed.  And worst case, remember that no trip will go exactly as planned and sometimes that’s just part of the fun!


In my experience, there are two main ways to plan for and adjust to weather that just won’t cooperate.

The first is to incorporate some flexibility into your travel plans.  Do you have a drive you absolutely must do?  Be sure to that you can make a last-minute switch with another day’s activities if need be.   

The second is to set realistic expectations.  Though that $300 flight to Iceland in November may be tempting, keep in mind that there is a reason for the cheap flights and diminishing crowds - less daylight and colder, rapidly changing weather.  Although shoulder or low seasons can still be a great time to travel, it’s important to be okay with the fact that outdoor excursions may be cancelled due to poor conditions.  For this reason, consider trips to cities that can be enjoyed despite wind, rain, or snow - such as Paris, Venice, or Budapest.  If you’re lucky, you may even have the top attractions all to yourself!

Grey Days in Reykjavik 

Grey Days in Reykjavik 

Accommodation Mishaps

I’ve endured a lot with hotels and Airbnbs: broken heaters, no running water, and to top it off an exploded air freshener.  Nothing is worse than arriving to a hotel in winter in Canada to find your room smells like an Axe bomb went off and the hotels solution -- open all the windows. Great idea in December.  

These kind of things happen and as funny as it is to look back on them now not having an inhabitable place to stay is extremely stressful.  If you find yourself in a accommodation disaster, stay calm and reach out to your host or hotel manager.  Take pictures, write notes, and document all of the issues are running into. If the issue is still not resolved then escalate to whoever you booked the accommodations through, such as Airbnb or Expedia.  Their customer service is great & in my experience they’re very accommodating to resolve issues.

In a case when you're tight on time and the issue is not easy to resolve book another place.  I was recently traveling to Sydney & arrived at my Airbnb to discover that there was no running water. None of the bathrooms or sinks a work, and to top it all off we were dealing with an unresponsive host and it was late on a Friday night.  Instead of stressing out, we started a case with Airbnb.  After realizing quickly that this was not going to be resolved fast because the host was not responding, we booked an alternative accommodation on Hotel Tonight.  Airbnb refunded us the cost of our apartment and covered the difference in price for our hotel.

Hotel Tonight - Radisson Blu Sydney

Hotel Tonight - Radisson Blu Sydney

Flight Delays

Flight delays are the worst! Airports are chaotic to begin with so hours spent smelling Panda Express, hearing couples argue, and babies cry is a nightmare.  For short trips try to fly direct.  This prevents the risk of missing a connecting flight.  Traveling international?  Make sure you understand how long it will take you to get through the airport and make sure you leave a little extra time just in case.  Try to have layovers in airports that offer multiple flights to your end destination.

If your  flight is delayed talk to your airline’s customer service and be nice! These people deal with angry customers all day and a little kindness can go a long way.  I had an experience where my flight was delayed in Chicago due to snow.  The United Airlines rep was working with was able to reserve a seat for me on a later flight in case I missed my connecting flight.  

If you have a tight connection try to book an aisle seat and let the flight attendants know.  Usually they will be more than accommodating to help you get off the plane first so you don’t miss your connection.

If you do have a flight canceled or majorly delayed make sure you read your airlines policy.  Many airlines will give vouchers for flights, food, and even put you up in a hotel.

Connections in O'Hare

Connections in O'Hare


Getting sick is bad enough.  Missing a trip because of it is the worst. Despite the best thought-out plans, an unexpected illness can put a damper on any trip.  

To reduce the potential illness pack any medications you may need.  I’m allergic to shellfish so I always make sure I bring allergy meds just in case.  Purchase travelers insurance to mitigate the most of extreme case of missing your trip trip entirely due to illness. This happened to a friend of mine.  He luckily was able to get the entire trip refunded through RoamRight, which offers affordable insurance covering both cancellations and delays for around $60 a trip.  

Travel mishaps happen.  Keep your cool and remember it’s part of the adventure!

x Smack