Do You Have a “Travel Season?”

Written by Dustin

Looking at my travel patterns, I notice there is a part of the year my travel is more frequent than others. I have started calling this “Travel Season.” Do you have a travel season?

It’s very easy to get travel envy, or think you are missing out by not traveling as much as others. In the real world (not Instagram), not everyone can jet off whenever they want. Sure there are people who work remotely who can, but I highly doubt it is the majority. While looking back over the last few years of travel, I have seen a pattern in our travels and have wondered do others have a particular “travel season” like we do.

Do You Have a Travel Season?

Work Interference

There is this thing called work that most of us have to attend 40 (or more) hours per week. Although “free travel” is great, those credit cards need to be paid, as well as other bills. Plus we all want some fun money, right?

Not every person can just book that awesome mistake fare that leaves in 3 days or a trip at the last minute for a 2 week stay in some foreign destination. Jeeze, my wife and I would need to jump through some serious hoops to just get an approval for a 2 week vacation. I believe most people have to actually plan their trips in advance because employers probably aren’t flexible enough for a last minute trip. There are probably some lucky people who can do that though.

Sure, we can maybe squeeze out a 3 or 4 day weekend here and there, but longer trips probably require some planning around work schedule. Frankly, work gets in my way of travel 🙂

Pattern for Travel

What sparked this post was looking at my travel history over the last few years. Our trips have been right around the same time over the last few years and it definitely wasn’t planned that way. We typically have been 4 to 7 trips per year. It has been increasing over the last few, but many of those are shorter trips over a long weekend.

When looking at our travels, we have definitely have a time of year where it is “travel season.” This starts in the Fall and continues through Winter. We seem to book a trip around our anniversary and birthdays as well.

Typically, we stay away from summer travel for a few reasons:

  • Ticket prices are higher. This could be for award redemption (more travelers = fewer saver awards) or paying for your ticket
  • I am quite impatient and hate standing in lines.
  • It is quite beautiful here in Maine with plenty of things to do.

My Travel Pattern

Last year, I started using My Flight Radar 24, to start tracking my flight miles, destinations, etc. It’s simple and easy to use.  This is something I wanted to keep track of, because I find it fun to keep track of that data.

Our larger trips, typically happen in January and October. Over the last 3 years, we have actually had a trip planned the same weeks in October. In January, it is usually around the end of the month.

This time frame has served us well. The award availability has been solid, with plenty of saver availability. As we have seen prices fall, it is becoming easier to plan for trips to Europe being on the East Coast. If we can have more than a week off, I’d like to get over to Asia as those tickets have been really well priced as well.

Also, getting approval for vacations is easier for us during these times. There is less competition for these time slots, so we plan on those times being available. With that in mind, it can take weeks to hear back about a vacation approval.

Looking beyond the approval for vacations, we do like to travel during off peak times. Outside of availability, the crowds are far less in these off season times. I hate standing in lines and look for options to skip them if I can. The weather for fall travel is probably my favorite, so that helps as well.

For our shorter trips, we typically have long weekend trips in late April/early May. We have completely stayed away from travel in the summer.  This could eventually change, but at this time it won’t. Then we usually book a few more trips on extended weekends (4 to 5 days) in November and December.

There are more trips added on, but those are our typical travel patterns. We could add a few more trips after Kristin earns more vacation time, currently she receives 2 weeks per year, which I am able to squeeze to about 3 weeks. In about a year, she will have 3 weeks, which means I  can squeeze 4 weeks in 🙂

Since we basically have a trip planned from October through January, I call that my “travel season.” We sprinkle a few trips in the rest of the year, but the bulk of our travel is located in those 4 months.

Knowing your Patterns

I don’t always have a destination in mind when I start planning my trips. When I start planning, my destinations are typically based on cost/award availability of the flights. There are so many places to see, so I am sure you can find one that works for you.

Having a goal is a key part of this game. While I might not know my destination at that point in time, I will know the potential countries I will want to visit. From there, I find airlines that service those areas and see which cards give me the most overlap for booking later on. This way I am able to open fewer cards, but it doesn’t take away my destination choices. I look for airlines/alliance partners that service these areas, and since flights have been quite cheap, I’ve been using our points as more of a cash currency.

If you are an off peak traveler like myself, you can very well find routes that cost fewer miles. This could be either by award charts, or using your points through their respective travel portal.

Knowing your travel pattern also lets you sit back and wait for better bonuses on credit cards. It is always great to have extra on hand in case you are able to squeeze in another trip, but planning ahead is really a key piece to traveling for less.


It definitely wasn’t planned to have similar travel patterns over the last few years. For our work lives, traveling in the off season works well for us though. Eventually, our work lives will change and that will allow for a few more trips. Traveling 4 to 7 times a year though, I really can’t complain.

Do you have a time of year you travel more? What patterns do you see in your travel history?

Don’t forget to Like me on Facebook, or Follow me on Twitter. If you have questions, comments or would like a topic, leave a comment. Thank you for reading!

Some of the links on Running with Miles are affiliate links that pay a commission if a purchase is made. Running with Miles is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to

About the author


After completing 6 years of pharmacy school, I finally had the time to travel. I started investigating ways to travel for less and when I redeemed my first award flight for my honeymoon, I knew I was hooked! Fast forward a couple of years and places I had never dreamed of visiting like Budapest, Honolulu, Bermuda and many other places where all within my reach, and for little to no money out of my pocket. Now, I have collected well over a million points and miles, and try to help people travel for less on their wallet.