The Best Time to Take Vacation

If you work a full-time office job, chances are you get some kind of paid time off (PTO). Taking a proper break in the form of a vacation is incredibly important for your health and work productivity.

Given the finite amount of PTO they can take in a calendar year, most people tend to be strategic about when they take time off to maximize time with their travel companions, whether they be family, friends or significant others.

This results in a lot of people wrapping their PTO around long weekends, Christmas holidays and other statutory holidays to squeeze the most out of their vacation. If you have kids, chances are you're taking time off in July and August, and probably during March Break.

However, if you have even the slightest flexibility in booking vacation, I suggest playing around with the dates and length of your time off to maximize relaxation and minimize trip costs. Here are six ways to get the most out of your vacation timing:

1. The extra "vacation" day from a long weekend doesn't necessarily outweigh the additional cost.

People love a long weekend getaway, or booking their vacation such that it overlaps with a statutory holiday. This usually works if you're departing mid-week and away for more than seven days. However, if you're just trying to squeeze a short trip out of your long weekend, you'll probably find that flights and hotels tend to be most expensive during these times. And due to everyone else wanting to do a long weekend trip, airports are usually incredibly busy and poorly staffed during these times, often leading to delayed flights.

Example: Let's say I wanted to take a trip to Orlando from Toronto. This flight is less than 3 hours, so ideally I'd want it nonstop. It is typically in the $400s in October...except when it's Thanksgiving weekend. Suddenly it jumps to $786 for a nonstop flight!

Is it really worth it to take the more expensive flight during Thanksgiving just to get the extra vacation day? Even if you were to use a vacation day on the following week, the cost of that extra day (i.e. if you treat it as an unpaid day) might outweigh the more expensive flight. We haven't even factored in hotels yet!

Of course, if you're taking 2-3 weeks off, you likely won't have this issue when overlapping with statutory holidays, other than around Christmas time.

2. Take vacation during off-peak travel times.

Along a similar theme to the previous tip, July and August are pretty much universally expensive no matter where you're flying to, if you're flying out of Toronto. The only exception is maybe flying to the South Pacific, where it's the dead of winter.

If you are flexible in when you can take time off, I suggest the following months:
  • Mid-to-late January
  • March (except for March Break)
  • April
  • Late August/early September
  • October (except for Thanksgiving weekend)
  • November
  • December (except for the second half of the month)

3. Start your vacation in the middle of the week. 

I can't remember the last time my vacation started on a Monday. Recently, I've been flying out on Wednesdays as they happen to be the cheapest flights. Most recently, I flew out on a Wednesday in May to Iceland for $260 roundtrip, and also flew out on a Wednesday in November to Sydney for $562 one-way.

I personally don't find it to be a hassle when wrapping up work right before vacation, as long as you give enough advance notice to your team.

4. Return later in the week, but before Sunday.

If you come back on a Thursday or Friday, chances are no one is going to give you a huge assignment on the day of, but will likely wait until next week. This also gives you time to unpack, do laundry, recover from jet lag, etc.

Returning on a Sunday means you have less than a day to unpack and settle back in, so for best results I suggest coming back on Thursday, Friday or Saturday.

5. Determine the length of time that really allows you to relax.

If you have three weeks (15 days) of vacation total, I suggest setting aside at least two consecutive weeks for a big vacation if you can. I've found that one week off is not really enough to fully get away from work, and depending on where you go, it may also not be enough to recover from a severe time zone difference.

That being said, if you like taking frequent short breaks in between work, by all means continue doing so - it's all about what works for you.

6. Go to a place in a different time zone.

There's nothing wrong with (sometimes necessary) staycations, but when you aren't staying too far away, people are more likely to bother you with "urgent" requests on vacation. 

When you're in a different time zone, especially when it's a 3+ hour difference, people are less likely to copy you on emails or give you a call as they know your response will be delayed. This is especially effective when you emphasize that you're in a different time zone in your out-of-office automated reply. When you receive fewer emails, it also creates less of an incentive for you to check them, allowing you to focus on enjoying the moment.


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