The award redemptions that forever changed how we travel

The Points Guy officially turns 15 years old Saturday, June 7. What originally started as the personal blog of our founder, Brian Kelly, has evolved into a powerful brand in the travel media landscape, with millions of readers and followers across our site and social media and video platforms.

We love hearing how points and miles have helped our readers travel the world, but for our anniversary, we wanted to take a trip down memory lane with our own staffers. After all, Brian’s own points and miles journey began with an epic family trip to the Cayman Islands back in 1996.

So, we posed a simple question to some of our longest-tenured TPGers: What redemption really kick-started your passion for points and miles?

Here’s what they had to say.

Nick Ewen

I started reading TPG in 2010, and at the time, I was a road warrior, racking up a ton of Delta SkyMiles and Hilton HHonors points (yes, there used to be a double “H” in the name). In fact, Hilton was the subject of my very first article as a contributor, which published in May 2012. But even though I was already part of the points and miles world, I wasn’t maximizing it, since I was focused almost exclusively on those two programs.

Then, in early 2011, Brian wrote about the ability to get two 75,000-mile welcome offers on American Airlines credit cards (which are no longer available). I jumped on it, and so did my wife — and later that year, we each booked Cathay Pacific first class to Bali, Indonesia, and back, along with a six-night stay using Hilton points at the Conrad Bali. I ate caviar and drank fancy Champagne … while wearing airline-provided pajamas … on a plane … as I sat across from my wife in one of our seats — yes, it was that big.

This opened my eyes to the incredible opportunities that come from leveraging both credit card welcome bonuses and partner flight redemptions — and lit the fire that started as a hobby, became a side hustle and eventually evolved into a career.

Summer Hull

As a kid, I grew up taking the traditional one or two family vacations per year — always by car, no matter the distance.

As I hit my early 20s, the family road trips were over, but what I had seen in the U.S. as a kid planted the seed to want to explore even more as an adult. However, I had a math problem. I had an entry-level social work salary, lots of New York University student loan debt and big travel dreams.

When my first big award trip came around in 2005, I had no extra cash, but I did have a stash of frequent flyer miles piled up from attending school in New York and visiting friends and family back in Texas.

As a grad school present to myself, I cashed in some United MileagePlus miles I had earned on those flights back home for a trip for two to Hawaii before starting my job.

Sure, we booked the cheapest hotel, barely left Waikiki and went to timeshare presentations (just to get a free breakfast and free luau tickets). But my feet were on Hawaiian sand, and I was swimming in the gorgeous Pacific Ocean. My thirst for travel — and my appreciation for the role points and miles could play in that journey — was born.

I really could see the world, go farther than the family car could take us and do it with a “currency” that was distinctly different from the one that would pay my bills.

Eric Rosen

Although my TPG colleagues rib me about my fondness for first-class flights these days, back in the early 2000s, I could only travel on a shoestring budget. So the trip that opened my eyes to the possibilities of points and miles was a backpacking adventure to South America.

I had a stash of American Airlines AAdvantage miles I had been diligently socking away since college. I decided to use them to fly to New York City for a weeklong stopover (when the AAdvantage program still let you do that at a gateway hub on international awards) for a friend’s wedding. From there, I flew nonstop to Buenos Aires and spent a month exploring Argentina inexpensively. I hopped over to Chile by bus for another few weeks and then flew back directly from Santiago to Los Angeles via Dallas.

My economy ticket — from Los Angeles to New York, on to Buenos Aires and then returning from Santiago — would have cost me nearly $1,100 had I been paying cash, which was well out of my reach at the time. However, I redeemed just 40,000 AAdvantage miles plus $52 in taxes and fees. This was a trip I’d been dreaming about taking for years, and airline miles were the only reason I was finally able to do so.

That was also the point at which I realized that points and miles could open up the entire world to me … and, indeed, they have done so since then, enabling me to do everything from swimming with whale sharks in Western Australia and seeing wildlife on safari in Botswana to celebrating family weddings in France and traipsing the temples of Angkor Wat in Cambodia.

And while it’s true that I do prefer to fly in business or first class, I’ll still jump at an inexpensive economy award to a far corner of the globe, so you might just see me on your next flight.

Andrea Rotondo

TPG’s early years opened my eyes to what was possible in terms of seeing the world without deep pockets. What I hadn’t expected, though, was how this hobby would coax me to stretch my boundaries, visit faraway places and connect with the people who live there.

My first big redemption was to South Africa. I transferred American Express Membership Rewards points to my Delta SkyMiles account (economy on the way — ouch — and blissful business class on the return).

I explored Timbavati and Sabi Sands nature reserves on game drives where I saw elephants, giraffes, Cape buffaloes, leopards, lions and so much more. I even did a few walking safaris. Despite my initial hesitation (fear), they were magical experiences, as I learned what life was like in this place so far from the streets of Boston, where I grew up.

Before I knew it, I booked more redemptions to places like Bali, Borneo and Vietnam — trips that pushed my physical and emotional boundaries. I learned so much from the people (and animals) I met along the way.

Points and miles have not only enriched my life but also taught me to be more spontaneous and take chances. It’s an unexpected gift that I treasure.

Becca Manheimer

Points and miles have changed my life and have allowed me to take trips and create memories that wouldn’t have been possible otherwise. In my nine years at TPG, my magnum opus was my honeymoon, an 18-day adventure with eight flights (including a seaplane) booked entirely on points and miles. This trip took eight months of meticulous planning, a few credit card sign-ups and help from my fellow TPG experts, but it forever changed the way I travel.

Some of our redemptions on this trip included:

• Qatar Airways Qsuite from Philadelphia to Doha to the Maldives for 70,000 American Airlines miles (a $6,000 ticket)
• Hong Kong to Newark in United Polaris for 80,000 United MileagePlus miles per ticket (a $7,400 ticket)
• Five nights at The St. Regis Maldives Vommuli Resort for 240,000 Marriott Bonvoy points, taking advantage of the fifth-night-free benefit

As TPG’s longest-tenured full-time employee (besides The Points Guy himself!), the bar was set very high. Growing up, I always dreamed of an amazing honeymoon, but the trip I planned using the knowledge we preach daily at TPG exceeded even my wildest dreams of what was possible.

Clint Henderson

I was relatively late to discover points and miles, only starting to use them regularly in my 30s. While I always loved to travel and have had an American Airlines AAdvantage number since 1997, I never really connected the dots. But after seeing my friends fly in first class and being super jealous of them, I was determined to figure out how I could do the same.

At the time, I was working as an executive producer in TV news and booking people like Brian Kelly and Summer Hull to come on and talk travel.

I learned a lot from those professional relationships.

But my first big redemption is what really locked me in forever. I booked Japan Airlines first class to Tokyo during cherry blossom season using my American Airlines miles. To top it off, I used World of Hyatt points to stay at the legendary Park Hyatt Tokyo.

That redemption forever unlocked in my mind the power of credit card welcome bonuses and points and miles.

I think it led directly to me making travel my career just a few years later, too. I’ve never looked back.

Katie Genter

I first fell in love with international travel in 2011 during a two-week trip to Turkey (which happened to be my first time stepping outside North America). But until a 2015 trip to Hefei, China, for the annual RoboCup robot soccer competition, my husband and I traveled within our budget by booking inexpensive flight deals and staying at inexpensive hotels and hostels.

But three redemptions for our 2015 trip to China made me realize the value of points and miles, even as a budget traveler. This realization led me to go all in on learning about award travel ahead of what I expected to be a gap year in 2017. (Spoiler alert: I never took the gap year but instead have lived as a full-time digital nomad for almost eight years.)

What were the redemptions? First, my husband transferred a Chase Ink Business card welcome bonus to United Airlines to cover his around-the-world flights to China (including two flights he reviewed for TPG). Second, I redeemed online travel agency rewards to book a train from Shanghai to Guilin, China. And third, my husband transferred points to British Airways to book me a short Cathay Pacific business-class flight from Guilin to Hong Kong.

Although not extravagant, these redemptions made the value of points and miles click for me. Best of all, they led me to dive into award charts and become passionate about award travel, which led me to start freelancing for TPG in late 2015 and accept a full-time role in 2019. So, in many ways, these redemptions changed the course of my life and led me to pursue a full-time career writing about points, miles and travel.

Ben Smithson

Working as a lawyer in Australia 12 years ago, I was desperate to find a way to fly in those “comfy seats up front,” so I spent hours of my free time scouring forums like FlyerTalk and blogs like TPG to learn the tips and tricks.

Enter the legendary U.S. Airways Dividend Miles program (RIP) with its sensible award chart, generous routing rules and the ability to simply buy hundreds of thousands of miles for 1 cent apiece during its endless promotions without ever setting foot on its planes.

Keen to take the plunge on a flight from Australia to Europe, my partner, who didn’t really understand how any of this worked, challenged me to book flights to the farthest point in Europe I could, so I managed an epic business-class redemption in 2013 from Melbourne, Australia, to Bangkok to Istanbul to Oslo, Norway, to Reykjavik for just 60,000 miles each leg flying Thai Airways, Turkish Airlines and Scandinavian Airlines. This epic journey of almost 12,000 flown miles was the first time the Dividend Miles agent who booked it had ever heard of Iceland, and it opened my eyes to the power of points and miles.

I have flown between Australia and Europe countless times since and will never sit in economy again now that I know how to get an upgraded seat for less.

Madison Blancaflor

Growing up, travel meant road trips to softball tournaments and the occasional trip to Disney World. Credit cards were something to avoid at the behest of David Ramsey books passed out at church. The first time I ever even stepped on a plane was my junior year of college.

Then, I got a job at Red Ventures, the parent company of TPG. I was introduced to the idea that credit cards could actually be a savvy financial tool, and I signed up for my first travel rewards card, the Chase Sapphire Preferred® Card (see rates and fees).

After hitting the welcome bonus, I used the points at 1.25 cents a piece via the Chase Travel℠ portal for round-trip tickets on Air Canada to Croatia for a trip with my best friend — something my 23-year-old self would never have been able to afford with cash. It was my first time ever leaving the U.S. and my first points redemption.

Though it was far from a groundbreaking redemption in terms of monetary value, that trip changed everything for me. It widened my world view, solidified a love for exploring the world and set me on my current career path. Not to be a complete sap about it, but I quite literally would not be where or who I am today without that trip and the love of points and miles that quickly followed.

Zach Griff

My obsession with points and miles started on a sad note. My great-grandmother had suddenly passed away in Israel, and my mom really wanted to make it to the funeral at the last minute.

Paid tickets from the U.S. to Tel Aviv were astronomically priced, but I happened to have a couple of thousand Delta SkyMiles left in my account. At the time, more than 20 years ago, SkyMiles still had some fantastic last-minute redemption rates, and I managed to snag my mom a business-class seat on a nonstop flight from New York to Tel Aviv to make it to the funeral on time.

Fast forward more than 20 years, and lots has changed in the world of loyalty, but it was that redemption that got me hooked and also changed my life (at the time, I had no idea I’d spend my career in the travel industry).

Since then, some of my top redemptions have included first-class flights on Lufthansa and All Nippon Airways, five nights at various top-tier Marriott Bonvoy properties around the world (check out Cosme, a Luxury Collection Resort, Paros in Greece) and, yes, even some last-minute domestic trips that would otherwise be unaffordable.

Bottom line

In some ways, it’s sad to reflect back on what used to be possible with points and miles, but despite ongoing negative changes to loyalty programs, there’s still a ton of value to be had. In the last month alone, we’ve used rewards to book our staffers in Emirates first class and Japan Airlines business class and at a Hyatt all-inclusive resort in the Caribbean, among other redemptions.

Our best advice? Focus on earning transferable rewards from your everyday spending. By converting rewards from credit card programs to airline and hotel partners, you unlock immense flexibility to travel the world in style, just like our staffers have done — and will continue to do for TPG’s next 15 years.