Take More Vacations: A Book Summary. Part 1.

I have been thinking more and more about travel recently, though I am not sure the time is quite yet right for me. (The thought of being unable to enter the country if I have a positive COVID test–and thus missing work–is a real challenge).

While cruising the Internet, I found this book by the founder of Scott’s Cheap Flights. I was intrigued, and decided to get it from my local library.

Cover of book, with a plane silhoutted against the sun, rising between two palm trees
Goodreads link to Take More Vacations. Not an affiliate link.

Mr. Keyes was previously a journalist, and his prose is easy to read. His book is peppered with anecdotes about people looking for deals. Not unsurprisingly, a number of them find success using his website.

He has a number of tips for finding cheaper flights, some of which I have used before, and some of which were new to me. I’ve decided to take notes on the book, to refer to after I return it. It’s entertaining enough I might decide to add it to my permanent shelves, but in the meantime, here are the highlights of the first 4 chapters.

Chapter 1. The Introduction.

Or, why cheaper airfare is important to your vacations, and some quick previews on how to find airfare deals (or at least avoid paying through the nose).

Here, the author proposes that expensive flights are a limiting step in taking vacations. He offers his interpretations of several cognitive biases that get in the way of us getting the best flight.

  • Loss aversion. We hate to see prices going up, so we would rather book a ticket at a not-so-great price, rather than risk having to pay a higher price. We may miss out on better deals this way.
  • Anchoring. If a fare used to be a certain price years ago, you may think it ought to be the same price now, ignoring the fact that over the past few years, prices had actually been running lower.
  • Recency bias. If you have been checking prices for a short while, and see the prices are steady, you may think they will never drop–and miss a good deal.
  • Sunk cost fallacy. By fixing too soon on a destination, you may dismiss a great deal to a similar destination.
  • Wishful thinking. Hoping that, for example, prices will drop closer to the flight, may not be true. However, by the time you figure this out, you are stuck with a higher ticket price.
  • Procrastination. (I’m not sure this is exactly a cognitive bias. Anyway.) Again, putting off bargain hunting for airfare will mostly lock you into a more expensive ticket.

He offers several strategies for getting a better price on a flight when you have less flexibility (dates and/or destination are fixed):

  • Try nearby airports you can drive to (I’ve done this).
  • Check fares from your homes and take a short positioning flight.
  • Check fares to airports near your destination and finish the trip in a different way (done this too).
  • Change departure and arrival dates (I play with this a little, but my vacation days are usually fixed well ahead of time).
  • Look for red eyes (Ugh).
  • Look at hidden city tickets (I have reservations about this one, as airlines have reportedly been cracking down on this).
  • Look as soon as possible, don’t wait to the last minute.
  • Use a stash of frequent flyer miles (done a few times).

He goes into more details in later chapters.

Chapter 2. Travel is good for you.

Mr. Keyes reviews a lot of data that come down to: Travelers are happier, healthier, and more successful. Personally, I’m not sure that I saw enough data to know if this is correlation or causation. In any case, he makes the argument that travel is good for you. I agree it’s good for me.

He goes through some of the deeper reasoning why spending money on experiences over things is better. (Mostly because we get to anticipate the joy of travel, travel, and then enjoy reminiscing about them.)

He then goes on to argue that it makes sense to make more trips in a year (shorter, cheaper) rather than one long trip. This lets you anticipate more trips, and it also takes the pressure off of any individual trip. After all, if you only take one vacation a year, it had better be awesome. If you take three annual vacations, one of them can be a relative dud without ruining the whole year.

He then states that getting cheap fares on your flights can make a huge difference in affordability, allowing a person to take those three trips a year, rather than being restricted to one every year or two.

Chapter 3. Make looking for deals a priority.

In this chapter, Mr. Keyes makes the argument that if you want cheap flights, you need to prioritize prioritize finding cheap flights.

This means that if you consider three variables–dates, times, and prices–you have to prioritize the price over the date or destination in order to get the best prices.

As a physician whose schedules set months in advance, this is a tough principle for me to follow at times. No last minute spontaneous flights for me. On the other hand, I could get some deals on flights months in advance, and then build my vacations around them. Also, I could be flexible about my destination (maybe I don’t go to Barcelona but I go to Rome, that’s not so bad) to take advantage of some great deals.

Chapter 4. How being flexible with your travel plans can save you money (and what to do if your plans aren’t that flexible).

Now we’re talking. What do you do when you have fixed dates and/or a singular dream destination?

For the dream destination:

  1. Look at airports that you can get to with only a little effort. If you can get a screaming deal from an airport that is only 2-4 hours away, it might be worth the travel time and travel costs (car drive and parking, bus or train ticket, even short flight) to get to that non-local airport.
  2. Be patient. Keep checking prices over a long period of time. Then, when you see a deal, pounce.

He then debunks several rules of thumb around the best time to buy tickets. I took away the following:

  1. Booking early does not mean booking as soon as the flight becomes available (About 365 days out from the flight). The airlines don’t want to underprice their seats this early, they want to maximize what they can end up selling them for.
  2. Also, last-minute deals aren’t really a thing anymore. Airlines would rather sell those tickets to business travelers who have to be somewhere at short notice; if they discount at the last minute, those businesses will just wait for the cheaper tickets. They would rather fly with an empty seat than give up that business income.
  3. Start looking for cheap tickets well in advance of the flight, and if you see a good price, do not wait–buy them while they are available!

What’s a good time frame to buy a ticket? He has a handy chart for that:

  • Off peak domestic flights: 1-3 months before travel
  • Peak domestic flights: 3-7 months before travel
  • Off peak international flights: 2-8 months before travel
  • Peak international flights: 4-10 months before travel.

He does suggest that if you haven’t found a great ticket and you are passing the suggested time frames, that your focus has to change. Instead of looking for a great deal, you now have to protect yourself from an outrageously priced ticket. I.e.: if your dates are fixed, at some point you have to buy your ticket before prices rise.

Are there cheaper dates to travel? In a word: yes.

Tuesday, Wednesday and Saturday are cheaper days of the week to fly, because it’s not as popular a travel day with business travelers.

Months without major school holidays are also cheaper, because you aren’t competing with all the people constrained by their childrens’ school schedules. (Those months are January, February, March, October and November, if you want to know.)

What if your dates are fixed?

If your dates are fixed, being flexible with your destination can still save you money. The idea being: if there is a deal for your dates, just book it.

There is also the option of rebooking certain tickets. For example, Southwest allows rebooking without fees. So if you have a ticket and a better deal pops up, you can rebook your flight and have a credit to use for later.

Or, if you have refundable tickets, you can buy the a cheaper ticket if a deal comes along, and then cancel the original, more expensive flight. (The order of operations is very important here; otherwise, you could be left with no ticket at all.)

I am stopping here, because my summary is running rather long. Next week (if I stay on schedule), I will review the next 4 chapters. They contain some interesting history and facts about airline travel, which changed how I think about looking for bargain flights.