It’s been four years since I booked a transcontinental round trip flight for $96, but like the flight I took yesterday, it was free.  Like being back in school, when I wrote that I wanted to show the math. The pandemic slowed my travel but not my desire to, nor my efforts to continue to fly for as close to free as possible.  Through a bit of savvy work, I was able to secure two sets of upgrades on an economy flight from Newark (EWR) To Seattle (SEA) flying United.  Here’s How.

In the four years leading up to the COVID-19 pandemic that started in early 2020 I traveled to 19 countries and all over America, racking up nearly 200,000 miles in the air and countless more from road trips.  While I now consider myself somewhat of a minimalist traveler, almost exclusively with a carry-on bag, I still manage to pack a fair amount of bits and bobs in.  A future article will come about my bags of choice, for now the focus is on things that have proven to be extremely helpful and not what if items.

I hunt plane ticket deals like it’s my job and do my best to take advantage of deals when I find them, as often as possible.  A few months ago a $121* round trip ticket from Philadelphia (PHL) to San Diego (SAN) came across my screen and I hopped on it.

If you are looking down while you are walking it is better to walk up hill the ground is nearer. -Gertrude Stein

The more I travel, the lighter my bag gets and the days of what if and maybe I’ll need are basically gone.  Now I can fit everything I need into a 50L Marmot Duffel for trips around a week, and have never had an issue using it as a carry-on. Longer trips or ones where I won’t have access to doing laundry I’ll use a Deuter 65L Travel Backpack that can easily be checked. I’m still a late packer, often doing it just hours before leaving and never using a list.  This leads to the first of my issues, and fortunately the one that brings me the least pain.

Adverse weather conditions will happen at the most inopportune moments, and usually cause most travelers a great deal of anxiety leading up to a trip. Even the most careful of planning can go sideways, and if you travel enough, will at some point. When this happens, look for the experience you can gain from it and don’t dwell on the photograph you’ve been planning on making for the months preceding the trip.

This is not an artistic photo with some deep meaning, this is the last photo I shot in a sequence before the water that’s hitting my camera wiped me on my ass and soaked me. None of my camera gear or belongings were ruined, just some bloody knees and shins, cut the webbing between my thumb and forefinger and a bruised ego.

I got to the hotel in Bangkok just after 10pm local time, after spending nearly 27 hours flying to Thailand and not accounting for the loss of day in travel flying west. In less than than 18 hours I’d be leaving Bangkok, heading to Siem Reap, Cambodia to tour Angkor Wat and some of the other temples in and around the city.