How to Travel More in 2019

Flying out of Ft. Lauderdale for the final leg of my 2018 travels.

It’s probably one of the questions I am asked most by friends, family, and colleagues. How do I travel more? Or more specifically, how do you travel so much?

While it’s true that I have traveled more in the past two years than all of my life combined, it would be false to say that this is too lofty of a goal for the average person.

Let’s go ahead and define “traveling more” as extending your budget to accommodate more trips than you would otherwise take. With that, I am going to share with you my top five ways I am able to travel as often as I do with the hopes of helping you to take more trips.

5. Cook More Often

This is something I have been employing for a long time, but it’s still very much worthy of sharing. By cooking your meals, usually in advance, you will save a ton of money over the long term.

For example, my typical work lunch of chicken breast, rice, and greens comes out to less than $4, whereas a typical “healthy” lunch in the Chicago Loop costs about $14. With some quick back of the envelope math, you can easily see a savings of $50 per week.

This doesn’t even take into account preparing your dinners and snacks at home as well. Of course, I dine out as well, but by limiting those meals to three per week, I am able to put aside more money for traveling.

4. Take Advantage of Work

This tip will certainly depend on what type of job you have of course, but you should absolutely take advantage of any travel opportunities presented by your employer. Whether it’s visiting another office branch or attending a conference, this is an easy and usually no cost way to travel more.

In my last job, I had the opportunity to travel to the company’s branch in Bermuda. This actually required me to get my passport — yes I didn’t have one at the time, although I had traveled internationally before — more on that later.

Later in that same year, I took advantage of my company’s unofficial policy of sending its employees to professional conferences (Live! 360 in Orlando). I opted to extend the trip a day to visit my good friend who lives in the area.

Check with your employer in 2019 to see if there are any travel opportunities for the taking.

3. Book Early

Here’s a tip that I’m still perfecting, but think I’ve got a good enough grasp of to share. By booking early, you can usually grab lower rates than if you booked a week or two before your trip.

How early? What day of the week? These are questions whose answers are forever in flux, so you must use your best judgment. In my case, I’ve found that between 2 and 3 months before gets me a pretty good rate.

I didn’t book my first Europe trip until about a month prior to takeoff and I certainly payed a couple hundred dollars more. The next time around, I was able to book early which gave me more money for adventures and better food!

2. Travel in the Offseason

Paris in the summer is amazing, Puerto Rico during Christmastime is fantastico, and NYC for New Year’s is festive. What all three of these scenarios have in common is that they are going to cost more due to being part of the busy season.

Last year, I traveled to Paris in November. Sure, the weather was a bit cooler and the days a bit shorter, but that didn’t put any kind of damper on my vacation. Maybe it’s because I’m an eternal optimist, or maybe I’m just a hardened Chicagoan.

In a couple of weeks, I’ll be traveling to London (yes, in January). I’ve already been warned that it will be cold. And rainy. Luckily, I can still have the time of my life and still wear fashionable clothes regardless of the time of year.

By planning your trips during off-peak times, you will certainly be able to travel more.

1. Utilize Credit Card Rewards / Airline Miles

This is my top tip for traveling more often in 2019 — use your rewards! Certainly, this won’t work if you’re in debt (if you are, get out ASAP!) but by putting your credit card rewards to work you’ll be taking more trips this year.

One of my cards gives me cash rewards, but I also have a travel credit card that racks up miles every time I make a purchase, and these can be redeemed against existing travel purchases.

In addition, I am a member of several airline miles programs — United, Southwest, Delta — and have been able to take a few “free” trips due to accumulated miles.

Definitely sign up for these programs where you can, they add up silently and before you know it, a free flight or two is on the menu.

I sincerely hope that this list inspired you to travel more often in 2019. Now, go out and take that next trip!

Do you have any tips on how to travel more? If so, please share them below, I’d love to see them!



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