I’ve spent the last decade traveling full time, and if there’s one thing I’ve learned — besides that, if it’s not a good time, it’s a good story — it’s that the costliest travel expenses aren’t always the obvious ones.
More often than not, travelers lose money through convenience fees, poor planning (or, adversely, too much planning) or the same blissful ignorance that has somehow floated me around more than half the world with just a single wrongfully boarded plane mishap, one pirate ship kidnapping and very few robberies. Despite the tales I’ve collected, that unawareness has cost me more than I care to admit at times (including, at the worst of times, everything on me).
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I’ve made all the mistakes so you don’t have to. Here are five of the biggest travel money traps I’ve encountered over the years — and what I now do instead.
1. Buying airfare without comparing prices
One of the fastest ways to overspend is booking the first flight you find. I always compare fares across Google Flights and Skyscanner, set price alerts when I have flexibility, check nearby airports and always browse in incognito mode. Spending an extra few minutes searching can easily save hundreds of dollars and is the reason I’m writing from Italy after spending $220 on a flight with friends who spent over $2,000.
While many travelers choose to book directly with airlines they prefer (and rightfully so, in order to use or gain loyalty points and have better customer service), third-party online travel agencies (OTAs) and aggregators tend to compete by offering lower prices.
For uncomplicated, direct journeys, I find that it’s generally worth the risk and sometimes the points loss. For multi-leg journeys, however, booking directly with the airline may make more sense in the event of delays and missed flights, since the airline’s customer support can usually get you on another flight without a lot of long phone calls or change fees.
I am always sure to search both one-way flights and roundtrip flights to compare pricing, in case a roundtrip ticket is more expensive than, say, booking two one-way tickets for flying from one airport and back into another. In New York, for example, it’s easy to mix and match between Newark, John F. Kennedy and LaGuardia.


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