Frequent Miler's latest team challenge, Million Mile Madness, is almost done! The last two weeks Greg, Nick, and Stephen competed to earn 1 Million SAS miles by flying 15 airlines. But who completed the challenge with the most Speed, Affordability, and Style?
The 2024 Frequent Miler annual challenge is over, with Flying by the Seat of our Points being won by Tim (congrats again Tim!)
Check out our contestant journals, recap videos, and more here. And follow us on Instagram, YouTube, and this blog to find out about our future challenges!
Tim, Greg and Nick were the challengers, with me and Carrie being tasked with crafting the challenge and acting as judges. We certainly didn’t have the travails that Nick encountered along the way, but there were numerous challenges and dilemmas we faced when planning Flying by the Seat of our Points.
We received a number of reader questions and comments during and after the challenge about how it was designed, so we wanted to share a little more about the thought process behind it, the considerations we had and the challenges we faced.
New Challenge Locations
We’ve run several Frequent Miler challenges since 2019, visiting a couple of dozen countries between us during that time. Seeing as we’d been able to showcase a little bit of each of those destinations in the past, we wanted to pick countries for each of the guys to visit that hadn’t been included with past challenges.
Never Visited Locations
Once the Frequent Miler team had settled on the concept of the challenge, Carrie smartly had us all share which countries we’ve visited in the past. In addition to picking countries that were new to our challenges, we wanted to assign countries to Greg, Nick and Tim that were new to each of them too.
Similar Time Zones
With Carrie on Eastern Time and me on Alaska Time (i.e. 4 hours behind ET) during the challenge dates, it was already going to be a little challenging scheduling the live check-ins so that we could all be present. As a result, when selecting countries for Stage 2 where the contestants all went their separate ways, we wanted to keep them in similar time zones.
Picking Cities/Countries With Luxury Hotel Options
With ~25 countries out of the running based on their inclusion in past challenges, we made a list of cities and countries that we thought could be interesting to send them to.
That list was whittled down a little by our desire for there to be at least a few luxury properties that each contestant would be able to book.
Visas & Vaccinations
With this being a last minute travel challenge, the three of them wouldn’t have a chance to arrange visas and vaccinations ahead of time. That meant Carrie and I would need to select countries that didn’t require vaccinations and which offered visas on arrival if applicable.
Navigating Foreign Languages
Dublin had been one of the cities originally on the shortlist. In fact, we’d assigned it to Greg for a while before deciding to change his Stage 2 destination. While it wouldn’t have been a huge advantage, we figured that if Nick and Tim had to navigate foreign languages, Greg should too.
Heading West Vs Heading South Vs Heading East
One of our biggest considerations was which direction around the world to send them in. Our initial inclination had been to send them west to Southeast Asia; that would’ve provided the opportunity to book some good business class products, plus they’d have a great pick of luxury hotels for reasonably-priced award bookings.
Researching this showed it wasn’t a great option though. I checked flights to each of the potential countries we’d send them to, with Thailand, Malaysia, Indonesia, Hong Kong and Taiwan being high on the list of potential countries. First I checked flights for June (when we’d actually be running the challenge) and then looked at flight options on Google Flights for a day or two ahead of time to get a sense of what last-minute flights were bookable even though that displayed cash rates rather than award options.
For the purposes of Flying by the Seat of our Points, this suggested that sending them west at the start of the challenge likely wasn’t a good idea. Due to flight departure times, connection times and arrival times, it looked like too much time would be spent traveling in that direction, with very little time spent on the ground.
Another option was to have them all travel to different countries in South America. Travel time down there was less of an issue, but when researching flights from South America to Europe, Africa or Asia, it looked like we’d have a similar problem going from Stage 2 to Stage 3 with this option as we would with Stage 1 to Stage 2 if we’d sent them to Southeast Asia first.
Another option was Western Europe to Eastern Europe, but this seemed like it would be less challenging on the flight front.
A fourth option was to send them all to Europe, then have them backtrack to send them all to Mexico City where they’d meet up.
Ultimately though, it seemed like US > Europe > Southeast Asia was the best overall choice. Travel times should be reasonable, they’d fit in well with our hoped-for livestream check-ins, there should be some good business class flight options from the US to Europe and then Europe to Asia, plus there’d be plentiful luxury hotel options for them to choose from.
Once we’d settled on that general routing, it was time to pick all the cities the contestants would have to fly to.
Picking Domestic Convergence Destination
Now that we knew they’d be flying to Europe for Stage 2, we needed to pick their Stage 1 destination. This was known as the Domestic Convergence because all three guys would be meeting up in the same city in North America.
A major east coast city like New York, Boston or Washington D.C. was under serious consideration. This would have the benefit of plentiful flights to Europe, with hopefully great business class award availability. Carrie and I decided against that though as we wanted the challenge to be, well, challenging.
Picking a North American city that wasn’t in the US was something under brief consideration, with Vancouver, Toronto and Mexico City all being options on that front. While that could’ve made things more interesting, we decided starting them in one of those cities would have less utility for Frequent Miler readers who are primarily based in the US, so you’d benefit more from them finding awards originating in the US.
Another option was picking a good-sized city not on any of the coasts such as St Louis, Cincinnati, Austin, Denver, Indianapolis, etc. Several readers advocated for that, or for an even smaller location like Des Moines. This type of location was a strong consideration, but we decided to go a different route.
That’s because a complaint we frequently hear from readers living on the west coast is that it can be extremely hard finding business class award availability to Europe from there. We didn’t doubt that was true (in fact, Tim already experiences this seeing as he lives in the PNW), so we thought it would be interesting – and challenging – to have the guys set off from there.
We didn’t want to make it too challenging though, so we sent them to Los Angeles as that has better international connectivity than other west coast cities like San Diego and Portland.
Sending the three of them to the west coast for Stage 1 also had another potential benefit. We thought that they’d assume they’d be getting sent to Asia next, so we’d get to surprise them when we revealed their European countries. That plan worked up until the last minute when Greg and Nick guessed that they’d be sent to Greece and Sweden respectively rather than the Asian cities they’d originally anticipated.
Similar Connection Requirements
In addition to making things challenging, we wanted to make things fair. We didn’t want to assign a country to a contestant where they’d have to take 2-3 flights if the other two guys would potentially have numerous nonstop booking options.
This didn’t quite work out as Tim did have one potential non-stop option pending availability, but we didn’t feel like that limited option would give him much of an advantage over Greg and Nick.
Contestant Comments
We’d considered a few different European cities/countries for Greg and Nick. Dublin, Lisbon and Greece had been on Greg’s shortlist and Bulgaria had been one of the countries on Nick’s. With Tim, we had fewer options as he’s visited most countries in Europe and so we’d already settled on Geneva or Zurich (both in Switzerland) for him.
We’d somewhat settled on Athens for Greg, Sofia for Nick and Geneva for Tim. However, during an Ask Us Anything livestream before the challenge we’d asked the three of them where they thought we’d send them. Nick said he hoped we didn’t send him to Europe, so that made us reconsider Sofia, Bulgaria for him. We wanted them to all be in a similar time zone and have similar travel times, so we looked at North Africa. He’d visited Egypt during a past challenge and Tunisia didn’t have a ton of good hotel options for the purposes of the challenge, but Morocco did have a number of hotel choices. Morocco also had the benefit of being classed as part of Europe by Air France/KLM Flying Blue, so that might provide an interesting award booking option.
I therefore researched flight options from LAX to Marrakech and Casablanca and there seemed to be several that would work provided there was award availability. Failing that, I figured he’d be able to get to Europe and catch a cheap flight from elsewhere or take a ferry from Spain, so we gave Nick his wish of no European country.
Cities Vs Countries
We continued to consider different European cities for Greg, Nick and Tim in the weeks leading up to the challenge.
We’d had Lisbon as Greg’s choice for a while, but then Carrie suggested that we pick somewhere in Croatia for him. Flight options in and out of Croatia seemed to work, but this left us with a dilemma – which city should we pick for him to visit? Split and Dubrovnik are both on the coast and each had a couple of interesting-looking hotel options via Amex Fine Hotels + Resorts and more. Zagreb meanwhile had better flight connectivity.
We had similar dilemmas for Tim and Nick. Should we send Tim to Geneva or Zurich? Should we send Nick to Marrakech or Casablanca?
We ended up coming up with what we thought was a good solution. Rather than giving each of them a city to visit, we’d assign a country. That would maximize their flexibility, thereby allowing them to book the best flight options, while also picking a city with hotel award options and attractions that interested them.
Asian City
After visiting Croatia, Switzerland and Morocco, we knew we’d be sending them to meet up in the same location in Asia, but which Asian city should we pick? Our decision was made a little easier by our self-imposed requirement that they only visit places none of them had spent time in before. Kuala Lumpur was the clear winner as somewhere that none of them had spent time in in the past, while having good flight connectivity and lots of luxury hotels to choose from.
Exploration Challenges
For each of the stages, we wanted to assign them some kind of Exploration Challenges. This too provided its own challenge for us. We’d need to assign tasks that were somewhat destination-specific in order to highlight the places they’d be visiting. However, we wouldn’t know ahead of time which cities they’d be visiting for Stage 2 and so the Exploration Challenges couldn’t be too specific there.
Carrie ended up doing a wonderful job with this, crafting fun tasks for each of the guys to complete that showcased the countries they were in but which would be achievable no matter which city they’d end up in, such as Nick needing to eat something in a tagine and Tim drinking absinthe (which is from Switzerland).
Livestream Timings
For each of the stages, we’d be checking in with the contestants live on YouTube. I mentioned in the Time Zones section earlier that Carrie would be on ET and I would be four hours behind in Alaska. This made things challenging when it came to choosing what time to arrange those livestreams, especially when it came to whether or not we should disclose those timings ahead of time. If we shared the timings ahead of time, the guys might get a sense as to where we’d be sending them. Not disclosing those times would make it harder for readers/viewers to watch the livestreams if they weren’t given much notice as to when they’d be. In the end, we decided to announce the timings ahead of time and hoped Greg, Nick and Tim would still be somewhat in the dark about where they’d be sent.
Our normal livestream time is 9pm ET, but that would make it 2am or 3am local time for them when in Morocco and Europe respectively. That seemed potentially cruel, although jetlag might’ve made that possible. In the end though, we settled on the much more reasonable 2pm ET which was 7pm and 8pm respectively for Stage 2.
For Stage 3, we wanted to plan the livestream at the very end of the challenge so that we could announce the winner during the livestream after we’d had a chance to award points for their hotel bookings and Exploration Challenges there. The time zone difference worked in our favor with this. Malaysia is 12 hours ahead of ET, so scheduling it for our normal livestream time of 9pm ET meant it would be 9am for Greg, Nick and Tim – late enough in the morning for them to have had breakfast, but early enough for them to catch a flight out later that day if they found some kind of great award flight for their way home.
Questions?
Carrie and I had many lengthy discussions about plans for Flying by the Seat of our Points, so I’m probably forgetting other considerations that we had when planning the challenge. Is there anything else you’d like to know about how the challenge was organized or why we made the choices we did? Let us know in the comments below.
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Hi Stephen, I’m not sure if you or any of the team mentioned this, but Malaysia Airlines has a Bonus Side Trip for those who can spend time in Malaysia after arriving from an international destination and going to another international destination at a later date. It’s basically a free domestic Malaysia ticket (you’ll have to pay taxes) to some of the other cities in Malaysia, much like United’s Excursionist Perk, but less convoluted
Check it out at https://www.malaysiaairlines.com/tw/en/other-offerings/bonus-side-trip.html
It was all entertaining enough to follow along, well done. 40k challenge is still the best, most relatable. Having a challenge start in a “second” domestic city would be even more relatable. How about Greg fly the team to a second city (which they don’t find out until game day) and then from there a 75k challenge to see how far one could go in business class, departing within 3 days.
I think these challenges are very fun to watch from afar, but somewhat impractical, in the sense that most people cannot book last minute trips. What if you tried to book only saver level tickets in business class for a group of 4 (let’s say) to various popular destinations during peak vacation times like a long weekend or Christmas? Each person would be given a popular destination and would be scored on how many of their segments met the goal (like if there were only 2 seats in biz and you booked 2J/2Y you might get half credit) etc.
I like this idea and will add it to our brainstorm list!
You’re probably right that last-minute travel isn’t as generally relatable, but for me (and maybe Stephen too) it was perhaps the most relatable yet. This challenge most reminded me of the travel Drew and I did during our ~5 ish years of full-time travel.
It’s a large part of my experience also, as an decently-heeled (if not well-heeled) early sixties guy with a family. And, it’s an important topic to understand even for people who routinely book ahead but either want to improve their trip at the last minute or may have last minute changes of plan.
One takeaway from this challenge that I’m not sure you guys have stressed enough is — it really is possible to get great redemptions last minute (as long as you don’t have to leave for Morocco on a specified Tuesday night without the option to layover in Europe for a day). Of the nine flights covered by the competition, eight went off without a hitch — plus all three of the returns went well too. And early June is not mid-November, it’s a busy travel season.
Every time they run a challenge, someone says “hey, this doesn’t apply to me and, therefore, it doesn’t apply to most people”.
For the record, I book last minute all the time, including for my family of 4 (my kids are adults). Last fall we were in Croatia (the good part, not Zagreb — Hi, Greg) and I booked all four returns (to different US destinations) in the 48 hours before departure. Do I feel that represents everyone’s style of travel? No, but neither does traveling at Christmas with four people.
I doubt that too many of the FM “players” are going to want to give up their family travel time for the challenge. And the appeal of the game is that we follow the players as they travel around, unveiling what they’ve booked / are booking as they go. How would that work if they had to observe the “typical” booking pattern of getting space the day it’s released, 331 days in advance? Assuming they continue to run the game in early June, they’d have to be booking their trips now, keeping them secret, and then reporting eleven months from now “here’s what I was thinking when I made this decision”.
So I don’t think that being “typical” is going to make for a good game. But I do think they could introduce a new podcast segment “Tracking My Trip” Greg and Nick could each pick a future trip they’re planning, discuss their initial booking on the podcast, and then give occasional updates as they refine (or possibly even cancel) the trip over time. I always find their teach-by-example content very valuable, and that would allow us to follow along, in real time, with a real, typical, ungamified, long term trip plan. Carrie could possibly even edit those segments together into a separate You Tube video for each trip, updating as updates are issued, to get some extra content out of existing material.
oy vey
I really appreciate your taking the effort to explain your underlying thoughts and reasoning.
Personally, I don’t think Greg would have been advantaged on the language front by being in Dublin. Maybe the opposite!
I like the regular daily content but never follow the Challenges.the last good Challenge was Greg getting ,1000,000 points/miles in a month when 1,000,000 was tough to get and that was 10+ years ago. Please stop the Challenges.
You should do a charity auction and let frequent miler readers bid on the chance to plan next years challenge.
Can you please add a like button to give us an option to like a post? I know there are like buttons in the comments section but I would really like one for the posts as well.
We used to have a feature that let people rate posts, but it seemed to be getting abused and so we ended up turning it off. The rating appeared at the very end of the post which makes sense as people should only rate it once they’ve read it, but it being located there means it doesn’t really help readers know in advance how good a post is.
I enjoyed following the challenge. Maybe this has already been covered and I missed it – but assuming Greg (as owner of FM) is paying for these trips – how does it work when each contestant uses their own points/mileage for these? Can you describe that in a little more detail? Does Greg reimburse somehow? But again, really fun to follow.
It has been covered. I believe the number mentioned was 1.5 cents per point.
again?
Yes, Greg does reimburse miles and points used for challenges like these. I think airline miles were being reimbursed at the same rate, with hotel redemptions being reimbursed more on a case-by-case basis seeing as there’s more of a difference in how much their points are worth, as well as accounting for other quirks like certificate valuations, FHR credits, etc.
Very cool. Again – enjoyed everybodys part in it. Thanks @Stephen.
FM,
Solo or couples travel is relatively simple and straightforward regardless of the destination.. I have a family of 3. Trying to find reasonably priced hotel rooms for 3 has been my biggest challenge in my travels. A family challenge would really put FM participants to the test (a scenario many travelers can relate to).
That’s functionally what last year’s “Party of Five” challenge was, if you haven’t checked it out.
This was last year’s challenge (5 people traveling together), although it didn’t include the one-room-for-everyone component. Personally, I think that’s a very, very specific issue to build a while challenge around but I think Nick has written about that issue (and if he hasn’t, he would be the person to do it).
As others have mentioned, our Party of 5 challenge did this last year, albeit having to find flights and accommodation for five people. In most cases, we booked two rooms – one for three of us and one for two of us. You can see everything related to the challenge here https://frequentmiler.com/tag/party-of-5/
Greetings from Dublin! Are there anything you or Carrie would have changed knowing what you know now? You both did a great job on judging and organizing the whole challenge!
Thanks! I don’t think I have anything that I would’ve changed. I’d certainly second-guessed our decision at the time to send Nick to Morocco when he was having issues getting both in and out of the country flight-wise, but I don’t think I’d change that if doing the challenge again.
Actually, one thing I would change is not being in Alaska during the challenge. Being 4 hours behind Carrie on the east coast and 9-10 hours behind when the guys were in Europe/Morocco made it harder keeping up with what they were up to, particularly in terms of us being able to score them for stage 2 in time for that live check-in.
The only very gentle comment I might offer is that the LA to Europe might have been a little too last minute. Once the players got off the call they pretty much had to find something available from only one bank of flights — the Tuesday evening eastbound departures. Even having the call five hours earlier the same day would have given them just a little more flexibility. For both of the other legs I think they had considerably more flexibility in terms of flight departures.
That’s a fair observation 🙂
This is tough because, like Stephen, I also started to kind of question the decision to send Nick to Morocco, but from a viewer standpoint, it actually is useful (and definitely entertaining) to show pitfalls and misadventures along with the smooth parts. And these challenges are indeed supposed to push our limits. Actually probably the thing I would have changed is Greg’s water-themed challenge. I had a few history-related challenges that might have been more fun for Greg, though I thought his decision to feature a bunch of locals by fountains was also clever.