How To Fly Cheap & Travel Often | Part 2

Part two of my two part series on how to travel cheap and often.

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It’s no secret you’re now blazing those travel sites for the cheapest fare but how do you go about visiting all your destination wish list?! Therein lies part two of our wonderful dissection of flying cheap and traveling often. Let’s take a moment to look back on my 2017 year of adventure in which I visited ten (10) cities, five (5) countries and had one helluva time on two (2) weeks holiday.

During that year I was able to take two (2) big trips overseas, a few stateside escapes and a couple of weekend benders. To be exact here’s a list of cities I traveled to that year:

Seattle, WA
Ossippee Lake, NH
Barcelona, Spain
Rome, Italy
Montreal, Canada
Portland, ME
New York City, NY
Columbus, OH
Atlanta, GA
Budapest, Hungary
Prague, Czech Republic

That got your attention right? Here’s how I did it and how you can too:

Seattle, WA 2017

Kind of a no-brainer to be honest. Most if not ALL of my weekend trips were done during long holiday weekends. It was easy enough to leave directly after work on Thursday to fly out, use a vacation day for Friday and fly home on Monday. If you sacrifice two of your ten vacation days you can really squeeze out a lot of those long weekends. Be sure to act first as others will surely have the same game-plan to lock those weekends down. This was how I was able to visit Seattle and Atlanta!

Vacation Day Counter: 2

This is the tough one but it is great if you plan to go overseas like I did. I flew out on a Friday afternoon and took a full five (5) vacation days off for my trip to Barcelona and Rome during the summer. By flying out on a Friday and home on a Sunday of the week following you really are UPPING your days away. This formula always netted me a solid eight (8) to nine (9) days away, less half a day for traveling. When you crunch those numbers those days away really add up!

Vacation Day Counter: 7


Work a few hours extra from Monday-Thursday so you can leave a bit earlier on Friday for some weekend adventures. I try to work an extra hour each day so I can leave at high noon on any given Friday. It’s worked out well and I was able to squeeze in a lot of those weekend road trips. A lake house in New Hampshire, Portland for some good craft beer, a quick getaway to the Big Apple or visiting the great north (*cough Canada cough*) for poutine. Anywhere that is less than a five (5) hour car ride is fair game for me on weekends so see what’s around your vicinity and have at it!


Vacation Day Counter: 7

*This tip is actually a game shark cheat code if I’m honest. You lose no vacation days if your work is cool with you leaving early and gain all the adventures. Definitely try this method out for anything around the area worth visiting!*

Thanksgiving as I have found has been THE CHEAPEST time to travel and with so many days off you would be stupid not to take full advantage. Of course for many this is one of the biggest holidays of the year so do so at your own discretion. This is where I use the remainder of my vacation days, around two (2) or three (3) left, throw caution to the wind and fly the heck out of here!

Budapest, Hungary 2017
Prague, Czech Republic 2017

I would take Monday-Wednesday off, while Thursday was a given for the holiday your Black Friday can be a toss up with work. My company doesn’t require us in Black Friday so it made leaving for eastern Europe that much more delectable. I coupled this method with tip #2 by flying out the Friday beforehand and getting my sought after eight (8) to nine (9) days of travel in. Let me tell you eastern Europe during those months are something to experience so DO IT!

Vacation Day Counter: 10 (FINITO!)

If you do it right and often you should be able to visit as much if not MORE than I have in 2017. It really was a great year of traveling for me all the while still being chained to the west’s notion of only two weeks holiday. This is a laughable idea if you asked others around the world and trust me I have! Thankfully with these tips I have accrued over the last couple of years of traveling it’s kept my mind sane and my appetite for adventure satiated.

There are big plans for the beginning of 2019 but first I have a solo trip to Costa Rica to look forward to!


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