TPG staff reveal their very first points and miles redemptions

May 14, 2020

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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.

An American Airlines plane fluttering U.S. and Cuban flags is seen upon arrival at Jose Marti International Airport on Nov. 28, 2016, becoming the first Miami-Havana commercial flight in 50 years. (Photo by Yamil Lage/AFP via Getty Images)
American Airlines was the first to operate a commerical Miami-Havana flight in 50 years on Nov. 28, 2016. (Photo by Yamil Lage/AFP via Getty Images.)

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

(Photo by Ileana Ravasio/Attimi Photography for The Points Guy)
(Photo by Ileana Ravasio/Attimi Photography for The Points Guy.)

In 1996, I used my dad’s U.S. Airways miles to fly him and my three siblings from Philadelphia (PHL) to Grand Cayman (GCM), and used American miles to fly my mom and me via Miami. It was all in coach, but the best trip ever. We rented a house on Rum Point from VRBO.

Related: TPG readers reveal their first points and miles redemptions

Becca Manheimer, Director of Marketing & Events

My first points and miles redemption was signing up for the old Chase Hyatt Visa (no longer available) that had a sign-up bonus for two nights at any Hyatt hotel in the world, and we did the Park Hyatt Tokyo. This was before I worked at TPG, and it was by far the most beautiful place I ever stayed!

Related: Stuck in translation: A review of the Park Hyatt Tokyo

Zach Honig, Editor-at-Large

An American Airlines Boeing 757 (N607AM) is seen at Miami International Airport. (Photo by Thierry Tronnel/Corbis via Getty Images)
An American Airlines Boeing 757 (N607AM) is seen at Miami International Airport. (Photo by Thierry Tronnel/Corbis via Getty Images.)

My first award redemption was during my sophomore year of college, in December 2005, flying from St. Louis (STL) to Orange County, California, for a sports photography workshop. The course fees were substantial for a college student, so the trip wouldn’t have even been possible without an opportunity to redeem miles earned with my American Airlines credit card.

I’m almost certain the award cost 25,000 miles, plus $7.50 in taxes, which was a standard amount for American Airlines’ economy redemptions at that time. American served many more destinations from St. Louis at that point, so I was able to fly nonstop to California, with a stop in Dallas (DFW) on the way back.

Related: Maximizing redemptions with American Airlines AAdvantage

Melanie Lieberman, Senior Travel Editor

My first-ever redemption wasn’t a knockout, but I’ll never forget my one-night stay at the El Mangroove, an Autograph Collection property in Costa Rica. I transferred American Express Membership Rewards points from The Platinum Card® from American Express to Marriott Bonvoy and redeemed them for a 60,000-point suite on Christmas Day. Considering there were only a couple rooms left and, if memory serves me, cash rates cost upwards of $1,000, I think I did alright for my first-ever redemption.

Ariana Arghandewal, Credit Cards Editor

My first award redemption was an ambitious three-country family vacation to Dubai, Afghanistan and Turkey. If that wasn’t complicated enough, my brother wanted to go on a separate trip to Europe to visit family … during the summer, which was notoriously tough to accomplish on points back in 2012.

I spent hours on the phone with airline reps who didn’t know Etihad was an American Airlines partner or where Abu Dhabi was. I also became acquainted with the concept of phantom award space, which made booking flights together even more challenging. At one point, I wanted to throw in the towel, but by researching routes and partner airlines, I somehow pieced the flights together using AAdvantage and Delta SkyMiles.

Hotels in Dubai were dirt cheap in the summer, so I booked the Hyatt Regency Deira for around $90 per night. I booked two club rooms, which included lounge access and chauffeur service to the airport. In Istanbul, I believe I redeemed 30,000 points for two nights at the Grand Hyatt (still one of my favorite hotels). We moved to the Doubletree Old Town for another four nights. My Hilton Gold status got us free breakfast and a ton of bonus points since it was a paid stay.

At the time, Hilton offered 50% off the cost of a second room if at least one child occupied it under 18. My sister was 15 at the time, so the out-of-pocket cost for two rooms during high season was around $1,400. Booking this trip was beyond stressful, but also incredibly satisfying. Moral of the story: Do your research, be persistent and it will pay off.

Related: The best hotel chains for families

Tom Grashler, Director of Video

My first points and miles redemption was last year. I used Citi points to buy a Northface winter parka for shooting in the arctic circle. My travel had been covered for years by my job (and we never got the points since we had to fly the cheapest route available!), but personal gear was not.

I didn’t have a parka that could stand up to -30F and didn’t want to spend my own money on it, so I used Citi points on Amazon, which I now know to be a very poor redemption. But that parka held up during a 14-hour shoot day in the arctic circle, so it was worth it.

Liz Hund, Writer

A Southwest Airlines Boeing 737-800 taxis at Denver International Airport. (Photo courtesy of Denver International Airport)
A Southwest Airlines Boeing 737-800 taxis at Denver International Airport. (Photo courtesy of Denver International Airport.)

My first redemption was a one-way flight from Kansas City (MCI) to San Francisco (SFO) for 6,000 Southwest Rapid Rewards points. I had earned the points from flying Southwest and using the Rapid Rewards shopping portal. My friends and I wanted to take a long weekend trip to San Francisco on a budget, so I decided to use my miles one-way and book a cheap flight on the other. I’d say it was a good redemption considering I was a broke college student without much cash to spare.

Nicky Kelvin, Director of Content, TPG UK

In 2011, I used 75k BMI Diamond Club miles earned from the then-BMI Amex and Visa double pack of cards, and a cheeky bump by setting up some kind of Diamond Club family account and crediting my dad’s only ever business-class ticket of his life on Qatar to Jakarta (CGK) to my Diamond Club Account. At the time, Qatar and BMI were partners.

The routing was all in business. BMI charged 1.5x of coach rates for business:

  • Frankfurt (FRA) to Buenos Aires (EZE) on Lufthansa
  • Buenos Aires to Santiago (SCL) on Air Canada (fifth-freedom route)
  • Bogota (BOG) to Newark (EWR) on Continental
  • Newark to London Heathrow (LHR) on Continental

Jasmin Baron, Senior Points & Miles Editor

My first ever redemption was with Air Canada Aeroplan miles in 2009, which I’d earned from a Canadian Aeroplan card I opened before I moved to the U.S. I used 50,000 miles to fly myself and my daughters (aged 3 and 22 months, respectively) from Toronto to Victoria, British Columbia, to visit my dad and stepmom.

It was a great redemption in many ways. I didn’t have to use miles for my youngest’s infant ticket (I think there was just a small fee), the flights at the time were running about $400 round-trip and my dad hadn’t spent much time with his grandchildren up to that point, so it was a really special visit.

Related: The best ways to maximize Air Canada’s Aeroplan program

However, at the time, I didn’t realize I could use Aeroplan miles to book United with no fuel surcharges. I was so bent on getting a nonstop because I was pregnant with my son at the time, and traveling with two toddlers on a connection was not appealing. However, I would have saved over $200 in taxes and fees had I booked from Buffalo or Rochester, New York instead with United Airlines, albeit with connections. The next time we flew out to the West Coast, I used Aeroplan miles again but avoided Air Canada, which worked out fine because the kids were older.

Clint Henderson, News Editor

I have to admit I have a problem with hoarding points. I used points a few times for friends, and once used a boyfriend’s points to fly us from New York to San Francisco in business class, but I’ve been collecting (hoarding) American Airlines miles for years.

(Photo by Samantha Rosen / The Points Guy)
(Photo by Samantha Rosen/The Points Guy.)

But then I learned back in 2016 that there was wide-open space available on Japan Airlines from New York to Tokyo. For my first significant redemption, those hoarded AA miles came in handy. I booked business class from New York-JFK to Tokyo and first class on the return, both on the Boeing 777. It was incredible.

I paid only 60,000 AA miles for the business-class flight and another 80,000 miles for the return flight in first class. I got to see the cherry blossoms in Tokyo and enjoyed two of the best flights of my life. I earned the miles from the Citi® / AAdvantage® Executive World Elite™ Mastercard®.

Related: The best airline award chart sweet spots

Caroline English, Social Media Producer

One time I moved into an apartment that the building that had a bedbug outbreak, so I used my bonus from the Chase Sapphire Preferred Card to cover the expenses of 1) professionally cleaning all my clothes, 2) moving out of that apartment (luckily it was when I was young and basically just had the clothes on my back). It wasn’t a great redemption, but it saved me because I couldn’t afford that debacle without it!

Andrea Rotondo, Senior Travel Editor

The first award redemption that I remember was back in 2006. We flew from New York to Cape Town on Delta Air Lines and returned from Johannesburg. We flew one way in coach and the return in business, which convinced us never to book economy long-haul flights again.

We’d decided to splurge on a big trip after our luggage was stolen in Hawaii a few months before, and we received a settlement check from the hotel. It turned out that the check covered an 18-day Ker & Downey luxury tour of South Africa, but we needed to find a way to book affordable flights.

I booked my award ticket with Delta SkyMiles earned from flying for work. My parents then gave us some of their American Express Membership Rewards points that we transferred to Delta to book my husband’s ticket.

Related: TPG readers’ best tips for visiting Africa with points and miles

Featured photo by Samantha Rosen/The Points Guy.

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