When to Spend: Why We Rebooked More Expensive Flights Back from Greece

Petani Beach, where we spent the last full day in Kefalonia before I woke up the next day feeling terrible.

Our approach to booking flights is usually frugality within reason.  We want to spend the least amount of money we can, but we are not going to sleep at the airport on an eleven-hour overnight layover or choose basic economy seats that leave us in separated middle seats for a long flight.  We also fly enough to have loyalty status with an airline, so regular economy seats come with a high baggage allowance and more free and reduced upgrade options than passengers without loyalty receive.

When we booked our flights to Europe this summer, we chose Milan as our initial entry point because flights to Milan were relatively inexpensive, we had never been to Milan before, and it was possible to get flights from Milan to and from the Ionian Islands.  We often use the entry-point methodology when booking flights to save money.  This means instead of looking for tickets to a specific destination, we opt to look for tickets to the region to which we plan to travel.  For example, instead of only searching for tickets to Phuket, Thailand, search for tickets in East Asia generally.  Out of the affordable tickets available, (1) consider which places you would not mind visiting for a day (or more!), and (2) check which go to Phuket for a reasonable price.  Then, book your roundtrip entry-point flights separately from your smaller legs within a region.

We booked roundtrip flights to Milan, our entry point, on United and their Star Alliance partners due to our loyalty status and then booked some short EasyJet flights to Zakynthos and from Kefalonia to get us around the Mediterranean.  Flying roundtrip through one city is almost always cheaper than opting for a multicity trip, a reality that I hate as someone who loves slow travel.  The trip-within-a-trip model is a way around expensive multicity trips.  The approach can save travelers on multi-leg trips a lot of money, but there are downsides when things go wrong.

When to Spend: Changing Our Flights

At the end of our trip, we planned to fly from Kefalonia back to Milan at 9:00 p.m., landing in Milan at 10:30 p.m. and staying at an airport hotel.  We then planned to fly out of Milan at 9:00 a.m. the next morning with a layover before getting home.  Doing the math, that meant probably getting to our hotel at 11:30 p.m. to go to sleep at midnight and getting up in the morning at 6:00 a.m. (or earlier for Patrick who planned to run first) for the next series of flights.

Our full-energy selves can deal with a single five-to-six hour night of sleep.  It is not ideal for optimizing health, but it works on rare occasions.  But late in the afternoon on the day before we were scheduled to leave Kefalonia, I felt a sore throat just starting.  Since I do not get sick much and can usually navigate my way out or illness with good sleep, nutrition, and rest, I initially figured I would be fine.

The day we were scheduled to leave Kefalonia, I woke up feeling miserable.  For the Whoop wearers out there, my recovery was 3%, and my resting heart rate was 79 bpm—the highest it has been since I got a Whoop in 2024.  After a month consistently running the Ionian hills, walking on a flat surface while carrying nothing felt like a workout.  I was actually sick, and I was not going to make three legs of travel with inadequate sleep in my current state.

So we changed our flights.  When we initially booked our roundtrip through Milan, we saw there was a multicity trip we could do for about $400 more per person if we wanted a nice direct flight from Athens to Washington, DC that left at 11 a.m. and got back to DC within five minutes of the original flight we booked.  At the time of booking, we did not want to spend $800 more.  That calculation changed when I could barely walk through my entire day and absolutely could not carry my own bag.

We paid the price to switch our flights.  We bought a new hopper flight to go from Kefalonia to Athens at 3:30 p.m. instead of Kefalonia to Milan at 9:00 p.m.  We got to an airport hotel in Athens early enough that I could eat dinner, watch a movie, and go to sleep at a reasonable hour.  The next morning, we could wake up naturally rather than before 6:00 a.m. and make our way to the airport at 8:00 a.m.  I even felt up to my normal morning walk the next day without forcing Patrick to supervise me to make sure I did not pass out along the way.  The full night of sleep proved essential to making it through the travel day ahead.

We booked a transfer to the Athens airport that morning, dropped off our bags in the United Premier lane so Patrick did not have to wheel both suitcases too long, found the lounge in Athens, and boarded a direct flight to Washington, DC.  More importantly, I was already feeling significantly better than the day before thanks to the rest and continued trending positively since I just had to sit and watch movies rather than worry about a layover and making a second flight.

We arrived back in Washington, DC five minutes earlier than originally scheduled.  We spent about $1,000 total to switch our plans, but my health was improving each hour rather than deteriorating from a lack of sleep and rest.

Balancing Frugality and Worthwhile Spending

Five years ago, I would have dragged myself through the original flight plan despite my health.  I may have even done the same two or three years ago.  Doing so would have left me sick for days recovering from the initial lack of rest.  This year, we could value my health above that $1,000, and that is the definition of wealth for me.  Doing so let me get back to my life immediately and keep all my plans for the upcoming weekend back home after five weeks away.

Our Premier Status with United certainly facilitated the change.  We can change flights at the last minute due to our loyalty, and we only have to pay the difference in cost rather than additional change fees.  I do not know if change fees would have changed the calculation, but I am happy that my travel-filled life made it easier to change travel in a moment when I needed it.

I am still someone who will choose to book the frugal flight option if at all possible.  But I find spending to guarantee health is worthwhile spending, and I would make the change again in a moment when my health is not optimal.  

This kind of thinking also has me looking for seats that allow us to sleep for an upcoming flight to Korea since I have gotten sick on one of the two trans-Pacific trips we took because of exposure to a sick person on a plane combined with my inability to sleep at all during the long flight.  Any overnight above 12 hours is now a candidate for fly-flat seats because I will enjoy the trip more if I am healthy.

Your own balance of frugality and spending may be different.  I can still deal with a short redeye to Europe, but the 15-hour trans-Pacific flights without sleep get me.  Your threshold may be different, but there are times to spend and times to be frugal.  Be frugal when you can, but spend in the moments that matter.