Weekend in Key West
I have lived in Southwest Florida for the better part of the past 15 years, but it wasn’t until last weekend that I finally visited one of the most famous ...
November 12, 2019
Meeting Minimum Spend
If you’ve ever contemplated opening a credit card for the sign-up bonus, you’re probably aware of some of the terms: “Spend $x,000 in 90 days to receive xx,000 points/miles”. I’ve ...
September 28, 2019
Useful Travel Tools: Service
This is the second post on useful travel tools, so perhaps I am starting a new series here at JoshOvermyer.com (albeit over a year apart). If you missed the first ...
July 25, 2019
4 trips to see Playing with FIRE
If you are reading this blog, there is a good chance you have already heard of the Playing with FIRE documentary and accompanying book, but for those who have stumbled ...
July 22, 2019
The ChooseFI guys say it all the time – it’s all about community and the genuine connections we make that help us along the path to Financial Independence. I live ...
June 12, 2019
Comprehensive guide to beginner Travel Cards
Obligatory disclaimer: If you are not a person who can pay off your credit card bills in full and on-time each month, stop reading now! The techniques in this article ...
February 27, 2019
President’s Day Road Trip
In my previous job with State government (circa 2014-2018), I was in a position without benefits. That meant no paid holidays, vacation or sick time, and no pension contributions. So ...
February 25, 2019
Twitter made me do it – New York City
It was only 10 days ago, on a Friday evening after work, when I learned my internet friend Dumpster Doggy was going to be in New York City for a ...
November 12, 2018
Travel hacking trips page
(This post will be maintained periodically) I thought it would be a good idea to share a list of the trips that my travel hacking [obsession] has allowed me to ...
July 24, 2018
A travel hacking sin
By Josh July 17, 2018 Sorry for the click-baity headline, but I truly committed a sin in the world of travel hacking earlier today: I bought POINTS with cash! To ...
July 18, 2018