We all know the time and effort that can go in to booking a trip. There is planning, execution, and anticipation. You have to pick the ideal destination around dates that work with your schedule, along with when weather will be nice, and the price is just right. There are flights, hotels, transportation, sightseeing to consider. Really, getting a trip to come together can sometimes take a lot of work.

But what happens when all your efforts are for nothing as your trip falls apart right before your very eyes? Many people have been experiencing this frustration lately. Having this happen creates a different type of travel stress to deal with as anticipation turns to angst.

The COVID-19 pandemic of 2020 caused mass cancellations and put the travel industry into a tailspin.

After seeing multiple trips fall apart in a short amount of time, it seems only natural that we would reflect on what lessons we have learned from this and share that knowledge with you.

Our Biggest Booking Regret

We have dealt with our fair share of trips that just haven’t worked out for one reason or another lately. But, they all have one thing in common.

Our biggest booking regret of the last year to 18 months has been booking trips too far in advance.

It seems counterintuitive. Booking a trip in advance has many benefits. Often times we book these trips because we have found a really good deal that just can’t wait. In addition to that we face the challenges of traveling from our small town. Flights are often expensive and limited; drives are distant. And, of course, we have to manage work schedules as well.

We started booking trips approximately one year in advance in the beginning of 2019. On the surface, it was so nice to know where our travels would take us for the year and be able to plan appropriately. It was nice to have everything in order and enjoy the anticipation of the upcoming adventure. But, there are too many things that can happen over the course of a year. We learned from personal experience.

Instead of creating a travel year that is well planned out for smooth sailing, the last 18 months have proven the opposite to be true. Booking trips so far in advance has resulted in us experiencing increased stress and frustration, having to make difficult decisions about whether to cancel a trip or trying our luck and, in some cases, even losing money on a few non-refundable purchases like event tickets.

In early 2019, we planned to end our travel year in the Bahamas. That fell through, so we went to beautiful Cabo instead!

Like many others, we have experienced countless trip cancellations and interruptions related to the COVID-19 pandemic. This is not the only scenario where we booked trips well in advance that ended up falling through. Political tensions in certain destinations and even excessive airline schedule changes that created misconnects have caused us to pull the plug.

We are always covered by travel insurance. But, many things along these lines tend to be on their list of coverage exclusions.

What We Will Do In The Future

When we look to the future of trip booking, we will likely do some things differently. While we still need to do a certain amount of planning in order to get time off work, we likely won’t book trips one year in advance. Instead, I foresee us requesting a certain amount of time off work, then seeing what deals are available in safe destinations as the date draws nearer and booking in a shorter time frame.

With any future bookings, we will always make sure to select options that are either refundable or offer full cancellation. Not just 95% of the time like we currently tend to do. We have learned that even with travel insurance, the wide list of exclusions does not cover most scenarios that we travelers are facing right now. Saving a little bit of money by booking the cheaper non-refundable option on a few travel elements has not been worth it.

Hotels can be expensive. Don’t try to save a few bucks by selecting non-refundable options.

I’m not just talking about plane tickets and hotel reservations. I’m talking about tickets to concerts and sporting events, transportation, admissions, excursions and activities. Make sure you can always get your money back!

Booking in a shorter timeframe gives travelers a better grasp of what the current events are and what things may impact an upcoming trip. We are living in uncertain times. Again, way too much can happen in one year.

We are simply not interested in spending hours sitting on hold with customer service, sending countless nagging emails, or loaning airlines our hard-earned money while we wait to arrive at the point in time that we can actually use the credit they will give us. Planning trips in a shorter time frame seems to be the way to go as we move into the new normal.

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  1. Oh my gosh – the two pictures at the beginning of this very informative posting are absolutely hysterical!! I laughed out loud when I saw these two pictures – a laugh out loud when I needed on a Monday! Thank you for a great and enlightening post.

  2. Wow! These lessons are the hardest learned. I admire you for being able to book things so far in advance normally. Most of my trips are last minute, but you offer great advice, like foregoing saving a few bucks for a non-refundable hotel room. Thanks for the informative post and sound advice

  3. I fly standby a lot as my mother is a flight attendant so as a family when we travel we always book refundable things as we never quite know how or when we are going to get somewhere haha! Loved the dishes picture too 🙂

  4. So your good in planning far ahead. Bummer that it falls true a number of times. We’re usually the opposite, will only take time of off work and book close by or just go and see were we spend the night.

  5. I tend to not book too far in advance as by the time I decide where I want to go, I am no longer in the ‘save by booking early’ window. I had returned from SE Asia and Australia towards the end of 2019 and was getting ready to plan my next adventures in January when all of travel went on hold. Even when I book late, I still insist on certain refundable items as I can change my plans on the spur of the moment.

    1. We are definitely narrowing down our planning window as well! Fully refundable options are the way to go for sure! I’m curious to see how it’s going to work though. We no longer want to purchase certain non-refundable things in advance – like admissions or events tickets. But, many places are now requiring pre-paid reservations for entry. I hope this doesn’t mean people who are gun shy on advanced purchases will lose their opportunities to visit/experience things. Guess we will see!

  6. Such a shame that you had to cancel all your plans, especially after being so organised. I think 2020 is the year that we will all remember for a long time 🙁

  7. This is such a true post. Who knew that we would be in a pandemic this time last year?! We also tend to book trips pretty far in advance, but we have learned to change that lately.

    1. It’s crazy how much has changed! I think things will continue to change for awhile, including how we book trips.

  8. So true. We have to do the opposite now with travel than what was our previous normal. I rarely booked refundable, but now you are right, going to have to do that as a norm from now on.

    1. We have never booked a refundable flight, but right now it doesn’t sound like such a bad idea for the future!

    2. I’m glad to learn we aren’t the only people who used to plan and book well in advance. Now, I feel like we have to be under-prepared for future travel plans!

  9. We’re all for planning ahead, but we’ve never liked tying up funds with reservations a year in advance. About the only time we do plan far in advance is for a cruise, or a really popular destination where hotel reservations are hard to score. (Looking at you, New England in the fall!) Thankfully, we didn’t lose any money with COVID, but three sets of plans got put on hold. 🙁 Here’s hoping everything starts looking up soon!

    1. Sorry three different plans of yours were ruined! Hoping New England works out for you though. Where are you planning to visit in that region?

  10. Such a helpful post. We got caught out once when we planned to fly to the UK and Israel’s main airport was closed due to incoming rockets! All worked out in the end but I bet that stands out as an usual reason to cancel a trip! #WeekendWanderlust

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