Why Traveling During “Shoulder Seasons” Will Change Your Wallet, Portfolio & Life Forever

Back when I started college in the fall of 2019 and planned out my freshman schedule, I was stunned at how many breaks were on the calendar!

I was both confused and elated like a kid on a snow day during the pre-Zoom era when they still existed. After evaluating all this time off, I’ve come to realize it’s key to happiness and success after all as long as you spend it wisely!

There’s winter, spring, summer, and dozens of days off and holidays in-between that by the time you add them all up, they stretch several months into the year. 

Whether it justifies the six-figure+ tution price tag is another question. Of course, as someone who can’t sit still, except for during the. lockdown when we had no other choice, finding time to travel, explore, and get out of the house, especially more than ever these days, is unexpectedly easier than I thought all thanks to shoulder seasons.

Recently, I came across the term, “shoulder seasons”. Imagine a shoulder, similar to a peak or trough in the markets, is a time of the year between the peak and off-peak travel seasons. 

It dawned on me that almost anything you can think of has a peak and off-peak season. If you’re strategic enough and want to beat most crowds and as a result, save your sanity, money, and greatest asset of all time, you want to sneak in your commute, deliveries, walk-in appointments, and vacations during shoulder seasons!

Back in K-12th grade, finding time to travel when prices were at reasonable levels was much more difficult and practically impossible since hotel and resort chains that heavily rely on tourism knew exactly when American travelers would flock there since in many states, winter and spring break are at set times during the year that haven’t changed for decades.

Booking an airline ticket a few months in advance at the right price can be rare to find for prime destinations such as Aruba, Florida, or Atlantis for spring break. Booking even a year ahead won’t let you in on the deals! You have to either stick to another destination entirely or travel at a different time if you aren’t locked into the K-12 schedule.

Now in college, there’s more flexibility and time off to explore which is really nice when it comes to shoulder seasons in the spring and fall. 

However, as someone who’s never actually gone away or taken a break for spring break due to lockdowns and work, I haven’t been able to take advantage of this opportunity! 

Next month will be my final chance!

As a working professional and in my case, an intern throughout college, work never stops, and mentally for me it’s even harder to take time off given the overload of work that keeps on running even when logged off. 

In terms of scheduling, it’s definitely a tricky balance since you need someone to always pull your weight when you’re gone and that takes work to manage. Although since you’re more in control, you can take time off that suits you best and your wallet almost anytime of the year.

So, if you do have more flexibility than the average HS student, how do you plan to strategically get to your destination on time with more ease and less headache while not stretching the wallet too thin?

Welcome to Shoulder Seasons

As you may expect, anytime from June — August then November — December, deals are limited for pretty much any popular hot spot, and if you want to get away for July 4th or Labor Day in the states, expect to pay double or a hefty premium, unless you have some exclusive deal, connections, or book as far in advance as remotely possible.

The only problem with booking miles in advance, no pun intended, is that our lives aren’t predictable and things change and come up all the time! 

You may have your plans set for Ibiza in May until something big gets announced that you cannot miss. These days, climate change has a mind of its own and we must account for wild weather as well to not wreck havoc on our plans.

As a planner myself, sticking to one that is months in advance isn’t always favorable anymore as there’s too much uncertainty in the air. 

So what to do in that case?

Know times of the year that are known to be off-peak or at least, less busy in general. Now, this doesn’t mean if you go to the same resort in April instead of in May it’ll be vacant and all yours, but you will notice a different crowd, possibly retirees, stay-at-home folks, WFH anywhere folks, instead of large families with young kids who follow the school schedule.

Up until the summer in the U.S. and Europe, May is by far the best month for both value and weather according to various reports and my own first-hand experience. 

Into the fall, September is also a nice month to squeeze in some down time. May and September are months that are packed with school-related activities since things are winding down such as with college graduation or picking up busy with back-to-school!

It’s never too early to start planning for that next getaway though. You deserve it. If you don’t, no one else will do it for you! 

Mid-August is also a good time to book something if September won’t work as long as you plan early and accordingly. Of course, this isn’t guaranteed everywhere or anywhere. The key is being flexible and expecting to spend a bit more each time since costs always come up.

In sum, there are dozens of factors to include on every trip. They mainly revolve around the price-point, location, if the place is a kid-friendly zone or not, exclusivity, etc. but for the most part, May and September seem to be the go-to months for the best deals in travel.

After the holiday airline havoc, the last thing you’re probably thinking is boarding another plane but that’s likely because the timing isn’t right. Everyone has the same idea of wanting to visit relatives over the holidays. Expect delays and long lines during common holidays.

A golden rule to remember is that slowing down can help you speed up later on, especially when traveling. 

Maybe for my next post I’ll weigh the pros and cons of flying private for those keen on hearing how to maximize the legroom and time plus headache of traveling. 

Clearly, the cost savings aren’t immediate when flying private but since time is money, it may be worth it for some of you to consider down the road or skies in this case!

Happy booking.