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Is the decision to carry-on or check luggage when you travel a struggle? If so, you are in good company! It is an age-old question that most anyone who flies asks at one time or another. There are fliers who clearly fall into one of the two categories and are adamant that is the only way they will fly. For others, the decision to carry on or check their luggage becomes a stomach churning, massive headache, nail biting endeavor. There are a zillion posts on the web about this issue, but let’s not make this decision more difficult than it needs to be. Here are a few issues to consider when deciding whether to carry on or check a bag.

Length of Trip, Where and When Are You Going

The length of your trip, where, and when you are going are the first issues to consider when deciding to carry on or not. Are you going to Cabo for the weekend in June? Unless you are a lifestyle influencer who needs thirty changes of clothes and fifteen pairs of shoes, a carry-on will probably suffice. However, if it is a weekend ski trip to Aspen in February, you may need a suitcase larger than a carry on to pack your winter parka, wool sweaters, and ski wear. This will require you to check your luggage.

Traveling for two weeks in Europe? This one can be tricky. Some people are minimalists packers who can get everything they own in their carry on suitcase or even backpack; while others could never imagine doing this. You probably know which you are. If you are the former, carry on. If you are the latter, check your bag and head to the gate or lounge! But, before doing so, you may want to determine your Hassle Factor.

Identify Your Hassle Factor

We think nearly every other issue falls into the Hassle Factor category, which we have unofficially defined as: Any factor that has the potential of negatively impacting your travel experience and enjoyment. We were thinking we could create a Hassle Factor metric ranking the elements Low Hassle, Medium Hassle, and High Hassle that travelers could use in making the decition to carry-on or check a bag. Because we all know what is a low hassle for me could be high hassle for you.

Hassle Factors to Consider When You Carry On

If you are a family traveling with small children, maybe you don’t want the hassle of having to wrangle suitcases while simultaneously trying to manage yourself and them. Maybe you have physical limitations that make it difficult to roll or carry a suitcase. Or how about this? Maybe you are too short or the bag is too heavy to lift and place it in the overhead bin. This then requires you to ask someone for help or risk dropping it on another passenger’s head. Oops! I’ve been the receipient of a few bag drops and I can tell you from experience, it hurts!

Speaking of overhead bins, they fill up pretty quickly these days. If you happen to be near the end of the line to board and the only bin space left is on row 28 and your assigned seat is on row 10, this can be frustrating for you and all the other passengers when it is time to deplane! How many of us have watched passengers pass bags over their heads up the aisle to get to the rightful owner? Or what is worse, the person on row 10 has to weave himself through the passengers that have already clogged the aisle to claim his bag at the back of the plane? What a hassle!

Hassle Factors to Consider When You Check Luggage

The two biggest hassel factors we see with checking luggage are the opportunity for bags to get lost/delayed/damaged and the checked baggage fees most airlines now charge. Both factors have the significant potential of negatively impacting your travel experience and enjoyment.

Many of us have arrived somewhere and our luggage didn’t make it. The recent Southwest Airlines fiasco during Christmas 2022 is a good example of this. Like the time we arrived in Paris on December 24th and my bag stayed in Dallas-Fort Worth and took three days to arrive. What was I thinking when I decided to pack my winter coat in the checked bag? Or the time we arranged a five-day bicycle tour around Prince Edward Island. All our lugguage and cycling gear went to Singapore. These events definitely received High Hassel factors from us, and I know these stories are nothing compared to what some fliers have experienced!

What We Do

For us as a family, the primary reason we opt to carry on rather than check a bag is that when we arrive at our home airport at midnight, the very last thing we want to do is wait for our luggage. Most often we can be home by the time our luggage arrives at baggage claim! Do we check bags? Yes, of course, but only when it is necessary, or more likely, when we are on our way back home. At that point, we don’t care too much if our bags go to Timbukto and take a week to arrive home. If it is something really important to us, we will find a way to carry it on the plane.

The key to a better travel experience is to come prepared and remain flexible.

Final Thoughts

Making the decision to carry on or check your luggage really comes down to being a personal decision. If you consider where you are going and when, and how long you will be gone, as well as what matters to you on the Hassle Factor, your decision should become much less complicated. Don’t overthink checking a bag. Your goal is to get where you need to go (hopefully some place fun) safely and with your nails entact and no headache!

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