The Frequent Miler Team’s First Award Redemptions

On our recent Ask Us Anything session, one of the questions asked was:

What was your 1st redemption?

Seeing as we only have an hour to answer as many questions as possible, we try to keep things as rapid fire as possible and so only Tim had time to answer this question. Once we’d finished recording, the five of us continued chatting for a while and started reminiscing about all of our first award redemptions.

It was nostalgic remembering our own first-time experiences making bookings with points and miles, plus it was fascinating hearing the diverse range of redemptions everyone else made. As a result, we thought it would be fun for all of us to share our first award redemptions with you.

Greg

As the most senior “elderly guy” in the group, it’s fitting that I’m the only one one the team who’s first award redemption predated this century.  And, it wasn’t even really my award redemption as much as my wife’s (who at the time was my fiancé).  For our honeymoon, in 1995, she used her American Airlines miles to fly both of us round-trip to Boston.  There, we rented a car and drove along the coast to stay in a B&B (no, not an Airbnb) on Mount Desert Island in Maine.  The B&B was right on the water and was located just outside the entrance to Acadia National Park and a short drive to Bar Harbor.  It was fantastic!

I don’t remember anything about how my soon-to-be-wife used her miles at the time.  I doubt she was able to book the award flights online back then.  I imagine she must have sent a request via telegram or pony express or something.

Stephen

I’m going to cheat a little and list two award redemptions. That’s because my first redemption wasn’t with points and miles in a conventional way, while my second redemption was at a significant stage in our life.

Redemption 1

I grew up in the UK and for the first five years of our marriage we lived in the UK (my wife is from the US). The points and miles scene isn’t as big over there, primarily because credit card welcome offers, card category bonuses, etc. aren’t anywhere near as lucrative as they are here.

We were skint back in the day, so I was always looking for ways to maximize things. Shopping portals were one method as they used to offer some extremely lucrative deals in the UK. For example, you could get a contents insurance policy (similar to renters insurance) for £50 for the year, but earn £150 cashback by clicking through from a shopping portal. At renewal, you’d cancel that policy and sign up for a new one, getting paid to do that each year for several years until they caught on.

There were also sometimes portal promotions offering bonus cashback when placing online grocery orders with the main supermarket chains and having it delivered to your home. This was back in 2006-2009, so we were ahead of the game with having that kind of opportunity. The larger supermarket chains also had loyalty programs and when placing online orders there were often promo codes you could enter to earn bonus points with them.

We ordered most of our groceries online from Tesco to take advantage of that opportunity, so we ended up accruing a ton of points. So many points in fact that in 2007 we redeemed them for lots of vouchers for a package holiday company (I think it was Thomson or Thomas Cook – I forget which one). We then redeemed those vouchers for a one week all-inclusive holiday to Lanzarote which included round trip flights.

In case you’re not familiar with Lanzarote, it’s one of the Canary Islands owned by Spain but which is off the west coast of Morocco and Western Sahara in Africa.

The Canary Islands are a popular spot for European holiday makers, particularly the British. The value of our vouchers would only get us so far in terms of dates which meant we had to travel in the off-season. That meant it wasn’t as hot in Lanzarote, but did have the benefit of not having to share the island with Brits who traveled there solely to watch the Premier League on a TV while drinking Foster’s in a British pub on the island which they could’ve done back home.

We have extremely fond memories of that trip as it was one of the first proper vacations we’d gone on since getting married a few years earlier. Most other travel had been back to the US to see my wife’s family and friends, with our budget not allowing for much other travel.

Lanzarote is a volcanic island, with one of the highlights being a tour to Timanfaya National Park and eating at El Diablo restaurant where your food is cooked by the heat coming up from the ground.

Another fun stop that day was to Cueva de los Verdes which were some pretty caverns with a fun surprise feature I won’t spoil in case you ever go there.

Redemption 2

While we did redeem points for that all-inclusive vacation to Lanzarote, those were Tesco Clubcard points rather than airline miles or hotel points. My first proper award redemption was for a flight on September 11, 2009 which is when we moved from the UK to the US.

We’d decided to move back to the US (well, back for my wife – first time properly living there for me) because we’d applied for a job in California as full-time foster parents at a group home. There was a slight problem though; although the organization seemed interested in employing us, they couldn’t proceed to the next stage of the application process until we were actually in the country. That meant we took the risk of getting rid of most of the stuff we owned, having my wife quit her job and moved from the UK to Virginia to stay with her parents while we waited to get interviewed for the job. I was fortunate that the international health insurance company I’d been working for in the UK was happy for me to work remotely until that job got finalized, so that reduced some of the financial risk.

We still weren’t in a great financial position though. Shae and I had credit card debt, she still had student loans to pay off and we were now down to one income and needing to ship a pallet of our items – plus ourselves – overseas. It didn’t help that trying to book one-way flights to the US were extortionately priced.

In case you’ve never checked pricing for non-award flights, flying round trip to Europe can be reasonably priced, but booking two one-way tickets can be extremely expensive, especially when departing the UK. I can’t remember the exact pricing, but I feel like one-way flights in economy were ~£1,000 from London Heathrow to Dulles, whereas roundtrip flights could be had for ~£400.

As I mentioned earlier, the points and miles scene in the UK isn’t as developed as it is here in the US and was even less so back in 2009. Despite that, I’d always registered with any and every possible loyalty program to earn points. One of those programs was Virgin Atlantic Flying Club as they were often who we flew with back to the US when visiting family and friends. Shae and I had both earned several thousand points with them, but not enough for a regular award ticket.

We were in luck though. Virgin had a Points + Cash option which let us each redeem a few thousand points with a cash co-pay of something like £200-£300 per person – far better than the ~£1,000 they wanted for cash tickets. As a result, we got excellent value cent per point-wise, even if it was only for economy class.

As a side note, being registered with Virgin Atlantic Flying Club came in handy about 6 months later when wanting to apply for my first credit card in the US. Virgin Atlantic sent me an email – presumably as a result of me changing my address with them from the UK to the US – giving the opportunity to apply for their credit card designed for expats. As a UK citizen living in the US, they were able to take into account my UK credit history to approve me for a card, even though it did get us into further credit card debt at the time (obviously not recommended). It also started me on the road to earning miles and points through credit card spend, so that worked out well in the end.

Nick

Since Stephen cheated, I feel like I get a cheat clause also. He double cheated, so I’m going to manage to talk about two redemptions while sneaking in a triple-cheat.

The reason for all this cheating is because my very first redemption wasn’t really a miles redemption either. Long-time Southwest Airlines flyers may remember that back in the day they didn’t have points but rather you would get a free flight after X number of round-trips or one-ways, and sometimes they would offer a promotion for double credit. I think if memory serves me correctly, I once or twice got a free round trip flight by flying two round trips (and I did something like a trip to Baltimore-Washington airport once just to get the second flight in so I could do a free round trip to Las Vegas I believe). My memory on that is a little foggy and I couldn’t find email confirmations from 2001 to confirm that story unfortunately.

However, I clearly remember my first miles redemption. It’s a very short story, so I’m going to cheat and also share my second mileage redemption — but let’s start at square one.

Redemption 1

My very first mileage redemption was awful. I don’t mean that to say that the flights were bad, but rather that the value was so laughably ridiculous that you’ll question how I came to be a blogger writing about this stuff (or better yet, hopefully you’ll realize that we all start at square one and can improve considerably).

My wife and I were bitten by the travel bug in what the young kids call the “mid-aughts”. My wife studied abroad in Australia circa 2005 and she and I left our “real world” jobs in 2008 to go teach English in Ecuador for the better part of a year. Then we galivanted around backpacker-style for a few years, working a lot of hours and then jumping on a cheap airfare when we could. We ended up in Hong Kong sometime in 2010 and we went to Macau (the “Las Vegas of China”) for a weekend. We rented an Airbnb room that was a shared space — essentially the spare bedroom of a couple’s apartment. The occupants turned out to be two Americans — a man who was a performer in a Cirque du Soleil-type show and a woman who owned a yoga studio in the US. We bonded over a shared love of travel and the woman told us about Flyertalk and ITA Matrix. I had never heard of either.

When I got home, I tried looking up those sites, but I was completely lost. Flyertalk was full of acronyms I’d never seen and I tried asking a few questions and got unfriendly responses. Our friend in Macau had mentioned something about fuel dumping and she had emphasized using ITA Matrix, but nobody would explain the former and the latter appeared to just be an airfare search tool that looked way more complicated than it needed to be. I didn’t get it and I mostly put it aside, determining that people had clearly figured out some tricks but that it would take me another lifetime to figure out their language. I gave up on it.

But apparently something about airline miles stuck in my mind.

Fast forward to 2012: Hawaiian Airlines opened a new nonstop route from New York to Honolulu. Introductory fares were $445 (Yes, I still remember that…..I have this weird memory for numbers). That was cheap enough that my then-girlfriend (and now-wife) and I decided that we had to go to Hawaii. We booked a round trip from New York to Hawaii and then separately I booked tickets to go to The Big Island (flying into Kona and out of Hilo I think).

I knew absolutely nothing about miles, but I knew that we had flown United (or I think actually Continental) to Dublin the previous January (for $280 round trip from New York) and to San Pedro Sula in Honduras (to go to Roatan Island) the year before and I had created a frequent flyer account with absolutely no idea how airline miles worked. At the time, I just figured that even if I never used them, it wouldn’t hurt me to have earned them. If I used them for anything, it was more than the nothing I’d have gotten if I didn’t sign up for an account.

As the trip to Hawaii neared and we read more about it, we decided that we really ought to also see Kauai. At that point in our lives, trips like this were expected to be once-in-a-lifetime events. I literally don’t think I knew anyone who had ever been to Hawaii for vacation — never mind twice. We figured this was our one shot so we decided to add Kauai a few weeks before the trip.

That’s when I remembered my United miles. I had no idea at all about how to use them.  I somehow got the idea to Google what I could do with my ~12,000 United miles and I learned that inter-island flights within Hawaii could be booked for 5,000 miles each way (flying on United’s partner Hawaiian Airlines). I don’t know whether it was possible to buy awards online at that point, but I wouldn’t have known how to do it. I called United Airlines.

After a long hold, I got an agent and I explained that I had some miles and I understood that they could be used for an award ticket on inter-island Hawaiian Airlines flights. She confirmed availability and quoted me the 10,000 miles round trip that I expected. But then she mentioned two things I hadn’t expected. In addition to the miles and $50 each way in taxes, there would be a $25 service fee and since I was within 30 days of departure, there would be a $75 close-in booking fee. She had said it in that matter-of-fact way that says “How would you like to settle that?”. Feeling embarrassed, I pretended that this was expected and totally fine and I paid the ~$110 in fees. I distinctly recall the cash price of those tickets: $77 each way. I paid $110 in fees for a $154 ticket. Ten thousand miles saved me all of $44….yielding a value of just 0.44c per mile. It was atrocious.

But the good news is that Kauai was amazing. We took a helicopter tour and saw the Jurassic Park waterfall and the Napali Coast.

And I was just in awe at the natural beauty of Kauai. Excuse the 2012-quality of the photos.

The good thing is that despite the fact that I made an embarrassingly-bad redemption, that trip was so amazing that we had to travel more. When we started talking about marriage not all that long after, we talked about one last big hurrah trip around the world. I knew nothing about miles at the time, but Googling information about round-the-world tickets led me to Million Mile Secrets and The Points Guy and I suddenly started learning about the power of credit cards. I spent about a year just reading everything I could (eventually graduating to Frequent Miler!) and then a year collecting miles and in 2015, we took a four-month honeymoon around the world. My second mileage redemption improved slightly upon my first when I used 45,000 American Airlines miles each to fly from Cairo to Tokyo in first class on Etihad.

That flight was the start of an entirely different life at which I frequently marvel.

My first award redemption was awful value, but it gave me the experience to know that it could be done — and without that first step a decade ago, I wouldn’t have gone on to the multitude of steps in the interim. So if you’re just getting started, take heart in the fact that your first redemption doesn’t need to be perfect to set you on the perfect path.

Carrie

Unlike the rest of the FM gang, I’m actually more of the “Player 2” in my family with my husband Drew behind all of our travel schemes and redemptions. So when we received this question during an Ask Us Anything, i had to go to him to try and remember what our first award redemption was.

When we first got married, we almost immediately embarked on a round-the-world trip that would take us most of the first year of our marriage. I had a vague memory that this booking involved British Airways somehow, but neither of us could remember the specifics.

Luckily, Drew and I had a blog in those days (Travel is Free) and he had written a post about that first ticket.  In the post, he said:

I started out with 370,000 British Airway miles when BA announced that they were changing their program. Under the old program you got unlimited stopovers as long as it was on the way. So last week I redeemed all but 50,000 for the following flights:

New York, NY – Hong Kong (1 Month Stopover).

Hong Kong – Jakarta, Indonesia (4 month stop over to roam around SE Asia).

Singapore – Sydney, Australia (5 week stopover).

Sydney, Australia – Auckland, New Zealand (1 month stopover).

Auckland, New Zealand – Santiago, Chile (3 week stopover).

Santiago, Chile – Easter Island (4 day stopover).

Easter Island – Lima, Peru (1 month stopover).

Lima, Peru – Miami!

Actually we did all that on 200,000 BA miles because 120,000 of those went to flying two friends (including my wife’s twin sister) NYC to Santiago; Easter Island; Peru and back to NYC, half the trip being business class. That means this entire itinerary was 100,000 points each person plus tax. What does tax look like? Well for my friends to fly from NYC – Santiago – Easter Island – Lima – NYC cost $140 (which is tax + fuel surcharges) and 60,000 miles (20k for economy down + 40k for business back).

There are a few holes in the story that Drew and I still had to talk through because, while apparently this is what we originally booked (according to past-Drew), it’s not what we remembered actually flying – at least not entirely. The Hong-Kong to Jakarta booking for instance didn’t ring a bell for us. (Instead we remember flying directly into Denpasar.)

Secondly, the Aukland to Santiago portion of our trip got modified somehow to make space for a business-class United-hopper stuck in the middle of everything as a trip within a trip. I know that we made it to Santiago to complete the original BA itinerary, but the Syndey – Santiago portion got changed somehow. In another Travel is Free post, I found Drew’s summary of our United “Pacific Hopper” booking here. (This also describes our brief foray with premium travel, as that itinerary is still one of the only times we’ve justified booking Business Class.)

We started in Saipan, as we got an Avios flight from Japan to Guam, and then after two weeks on Guam got a super cheap flight to Saipan.

Here’ s the trip:

1. Start Guam/Saipan
2. A day (17.5 hour) layover in Singapore
3. 2 weeks in New Zealand
   1. 8 days spent in Fiji
4. 2 weeks in Rarotonga
5. A night in Sydney
6. Layover in Tokyo… where we just got off the plane

Pretty good for 25k/40k, right?

Although the ticket kind of started and ended in Japan.

In that post, Drew went on to say:

At that point in life, our travel was more like a gap year. We had a totally different mentality, and were probably the most frugal people (at that point) I think I’d ever met. I mean, we were traveling indefinitely with no income, burning through little savings.

So in Guam, we were car camping… in a beater car. Until we made friends with a stranger who ended up hosting us for the second week.

In Saipan we coachsurfed.

In Rarotonga a hitched ride led to an opportunity to stay in a stranger’s rental house, which was in between tenants.

But we’re also flying business class all over the place. I can’t imagine what people would have thought. Hippy trust fund kids? It would’ve been hard to place us.

But anyways. The Singapore Airlines lounge was about the most glorious thing I’d ever seen. So much food… and so much good food.

Oh, and the Thai lounge gave us each 30 minute massages.

It was otherly.

I wish I remembered better which credit cards we’d signed up for to get all those British Airways “Miles”.  As perhaps a little clue, here’s what Drew wrote in that same ancient post about the round-the-world British Airways booking:

My recommendation is to wait until Chase runs the 100,000 miles British Airways credit card promotion and then sign up (who knows when that will be, but I’ll let you know). And/or wait for a big American Express promotion and wait for British Airways to run a 50% bonus promotion where you get 50% more for transferring to British Airways.

I think the American Express transfer bonus to British Airways was what we’d done somehow…

Even though I don’t remember a lot of the specifics of that booking (and can’t properly scrutinize how good a use of miles it was), I do remember what a thrilling adventure that was. Just like Drew described it above, it really was “otherly”. One day we were living in luxury, and the next we were slumming it in some $10 hostel or homestay. No day ever looked the same and I remember living in a kind of chronic mental stimulation where it was impossible to build routines of almost any kind for nearly 10 months. Living that way at 25 years old, I think that trip actually helped shape some pretty big pieces of my personality and lifestyle now. It’s probably to blame for my restlessness, but also probably to credit for my preference for minimalism.

Tim

Do you know how to spell boring? T-I-M. That’s exactly what my first award redemption was, even though at the time I thought the most exciting thing in the world was that I was getting a free flight. And it all happened because of my honeymoon.

I wanted to plan an epic trip that went around the world and hit the majority of the top-five countries on my soon-to-be-wife’s bucket list. Since I was a dirt-poor college student, I did medical research studies during my last couple years in school and then saved the cash for the trip (I wonder if that’s why I have that 11th finger now?). I secretly planned for months and finally booked a round-the-world Star Alliance ticket that went from Omaha-Denver-Maui-Honolulu-Auckland-Brisbane-Singapore-Johannesburg-Capetown-Frankfurt-Paris-Dublin-St John’s Newfoundland-New York City-Chicago-Omaha. My poor wife had no idea where we were going or how long we would be gone. She only had a temperature range to plan for and then found out the destinations as we went.

The internet was just getting going in the those days, so one of the most invigorating moments of the winter before we left was getting a manila envelope in the mail with two stacks of stapled-together tickets, printed on actual ticket stock. Flipping those seventeen segments back and forth sounded like pure adventure to me. Man, was it ever. We had an incredible time going around the world in 100 days, helping to spark a passion for travel that’s never abated. In the process, we had a flat tire the night before we left New Zealand, took out two sideview mirrors in Ireland and put a massive gash in an oil pan in South Africa. We also got speeding tickets in four continents, something that still makes me proud more than twenty years later.

In any event, I was working with a travel agent in San Francisco over the phone. Before he ticketed the trip, he asked me if we were members of any Star Alliance frequent flyer programs. I knew that we had both signed up with United before an international trip a few years before and that’s where we credited the miles. Those were the halcyon days when United actually credited miles based on distance flown, so we each ended up with around 30,000 miles when all was said and done.

I had no idea what 30,000 miles would get us; I figured maybe a free meal or an upgrade to first class. I was shocked to find out that, if we put our miles together, we could get two roundtrip tickets to almost anywhere in the United States. We moved to Montana after we returned from our honeymoon, and airfare back home for the holidays was quite expensive. So, I called up United and was absolutely thrilled to find that I could get those $500 tickets completely covered with our miles. Given what we were making back then, $1,000 in airfare that we didn’t have to pay for felt like we’d won the lottery.

All that to say. My first award redemption was…wait for it…roundtrip from Missoula, Montana to Omaha, Nebraska on United Airlines. And I was bragging about it all Christmas.

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