TPG staff reveal their very first points and miles redemptions
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Even though the staff at The Points Guy aren’t traveling right now, we’ve been reminiscing on our best points and miles redemptions. We’ve redeemed millions of points and miles to get to and stay in the Maldives, to fly the best business-class product in the world, and to stay in all-inclusive resorts in the Caribbean.
But before we came to TPG, we were all points and miles beginners. Some of us have better stories about our first points and miles redemptions than others. For some TPGers, their first redemptions saw them fly business class to Europe, while others experienced (expensive) growing pains.
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Before we get into my colleagues’ stories, I have a secret to admit. My first points and miles redemption was a disaster. It was laughably bad, considering what I know now about points and miles.
My first job out of college was at a national newspaper. I started during the onset of the 2016 presidential election, which meant I got to do some traveling. I flew several paid flights from Washington, D.C. to cities in the Midwest, including Des Moines (DSM) and Cedar Rapids (CID) on American Airlines, earning several thousand AAdvantage miles along the way.
I also earned a bunch of miles after flying a mistake-fare ticket from New York-JFK to Ho Chi Minh (SGN) on American and Japan Airlines. For my 24th birthday in February 2017, I decided to take a trip to Havana, Cuba (HAV). This was shortly after the Obama administration eased travel restrictions to Cuba and airlines, like American, allowed you to book tickets using miles.
I had very little understanding of points and miles at the time, let alone anything about valuations or redemptions. This was back in 2016 when I redeemed every single one of my American Express Membership Rewards points to wipe my statement charges. I only really knew about points and elite status after my boss said he’d flown to Singapore for a day and a half, just to keep Delta Medallion status.
After looking up flight options and wanting to save a buck, I remembered I had AAdvantage miles. Then I did a big no-no. I booked a portion of the ticket Baltimore (BWI) to Charlotte (CLT) to Havana (HAV), returning back to Washington (DCA), using 15,000 AAdvantage miles plus $47. I thought that would cover it, but then realized I had to book a second ticket in cash, which came out to $130. After spending nearly $180, I realized I should’ve just booked the ticket in cash as it was only a few dollars more.
Lesson learned. Here’s how other TPG staffers fared.
Brian Kelly, The Points Guy
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