Contrarianism: Steal Investor Secrets to Win at Travel-Booking

Okay, so first of all, I want to tell you that nothing I share with you in this post will put you on the wrong side of any governmental agency; if you came here looking for insider trading tip-offs, this is not the place. What I will teach you in the next five minutes is how to use one of the most important tools of savvy investors and some of the ways it can benefit you next time you're planning a trip.

Laying the Groundwork

Some of you may already be familiar with the term "contrarianism," but just to be clear:

Definition: A contrarian is a person who takes up a contrary position, especially a position that is opposed to that of the majority, regardless of how unpopular it may be.

In the stock market, one of the most potentially lucrative strategies is to "buy when there's blood in the streets," when things aren't looking so good and people start panic-selling, because that is when the market is sure to be trading at a discount. Wouldn't you also like to buy your vacation at a discount?

Translating Contrarianism into Travel-Speak

Contrarianism in travel is simply taking advantage of the opportunities the come from behaving in a manner counter to the way most travelers behave when booking flights, hotels, and other travel activities.

Monday-Friday work schedules dictate that most people want to fly on Fridays and Sundays or Mondays. It's not too hard to get a day off on either side of the weekend or one solid week (book-ended by two weekends), which means Tuesday-Thursday typically get less attention from vacation-goers. If your job or other obligations doesn't entirely preclude flying midweek, you'll find better prices and more award space.

The time of year you travel also has a huge impact on the cost of your trip. Certain destinations are packed with visitors all summer and almost entirely devoid of them the rest of the year. Make note and take advantage! If you've got American Airlines miles, for example, you can travel roundtrip from the US to Europe for just 40,000 miles from mid-October to mid-May, which is a great value. Many destinations all over the Northern Hemisphere also get a healthy price-cut in September despite continued good weather when families return home for the new school year.


Potential Obstacles to Contrarian Travel (and Some Solutions!)

Contrarian travel is not always easy and it's not always the right play. Here are some potential obstacles to booking travel with a contrarian mentality:

  • Off-season is off-season because the weather is reliably awful
  • During the slow-season, many tourist-catering businesses shut down
  • It's difficult to be a contrarian with a regular work-schedule and/or family obligations

The third one is a toughy, but the other two are only a problem if you don't do your research. For example, Croatia is a beautiful place and I would go there every summer if I could. However, winters along the coast bring cold, stormy conditions that make it impossible to live the bikini and tank-top lifestyle that makes the Croatian coastline so desirable. If you want a shot at some off-season sand and sun in Europe, southern Spain would be a better choice.

Conversely, visiting places like Belgium or the Netherlands during the heart of the cold-and-dreary winter might not be bad at all. You won't see tulips in bloom, but major cities in these places are loaded with indoor activities like art exhibits, music performance halls, and coffee shops (and there's never a bad time for Belgian beer). When looking for contrarian destinations, think about what makes a place special and whether or not the off-season totally negates that thing. If not, that could be your discount opportunity!

An Actionable Strategy for Finding the Best Travel Deals through Contrarianism

If you want to spot and take advantage of contrarian opportunities all the time, ask yourself these two questions: When do people most want to do the travel activity I'm interested in? If I do it at another time, will I still be able to enjoy my experience?

If you can identify the answer to the first question and you feel good about the second one, there is most certainly a way to profit. There's also no need to limit this strategy to the big items like flights and hotels. Here are two real-world examples of contrarianism helping with the little things:

When Johanna and I visited Bucharest, Romania on our honeymoon, we heard about a famous restaurant with incredible architectural detail. We went to Caru cu Bere around dinner-time the first night to find it so crowded that we ended up in the hot-and-sweaty basement beer hall and bailed almost immediately. Undeterred, we came up with a new strategy and returned for lunch the next day. They were able to seat us in the main dining hall, where we enjoyed the beautiful designs and had an excellent meal, including the largest beer I've ever been served (1000ml: that's three beers in one heavy, glass stein).

I also discovered while booking our vacation to Croatia that the cost of boat/jet ski/car rentals goes up 20-30% between the end of June and the first of July. We planned one of our splurges of the trip (a convertible to explore the Island of Hvar for a day) to occur just before the price-change took effect and saved $30.


Perhaps the very best contrarian strategy I've come across is one of the easiest for me to put to action: plan ahead. People lead busy lives, often lack direction or the time to look up, and as a result, planning ahead is at an all-time low. Consider that hotel rates often rise by 20-50% within the last month or two of travel. You can book a hotel six months in advance at a healthy discount and usually still retain the ability to cancel your reservation within three days of the planned stay. It pays to think ahead!

The Bottom Line

While contrarianism in travel won't make you filthy rich, it can make you rich in experience. Next time you're planning a trip, instead of thinking about what's in-season, consider using my contrarian strategies to have a more unique experience and save money at the same time. DO MORE AND LOVE EVERY MINUTE!