You can do almost anything with miles and points…or so we’ve said. Can Greg, Nick, and Tim make dream trips out of destinations and credit card welcome offers selected randomly from a deck?
Every year, the FM team does a team challenge where we compete to see who can make their points & miles go farthest. We’re calling this year’s challenge “The Wild Card Challenge”. In today’s episode, we’ll give you the high-level overview, but this post will share more details of the challenge as well.
Introducing the 2026 Team Travel Challenge: Wild Card!
Our contestants will pick from wild card decks to select which hotel, airline, and transferable points cards will provide their points and miles budget, then they’ll select their travel destinations from another deck. And finally, they’ll select power-ups and obstacles to make their travels a little more realistic to the challenges our readers and listeners face. We’ll find out if they can build amazing trips from these randomly selected variables!
Since Stephen won last year’s 100K Vacay challenge, this year he’ll be sitting out and serving as judge alongside yours truly (Carrie). That means our contestants will be Greg, Nick, and Tim. Similar to our 2024 Flying by the Seat of our Pants challenge, the contestants don’t know much about their trip parameters yet, but they all seem quite confident they’ll be able to make something impressive out of whatever cards they’re dealt!
What are the wild card decks?
Destination deck: Contestants will each draw cards from our destination deck to reveal their first and second travel destinations. (The third and final destination will be a joint destination assigned by the judges.)
Credit card bonus decks: Contestants will then draw three cards from an airline card deck, a hotel card deck, and a transferable point deck. For their trips, they’ll be able to use the welcome offers from these cards as well as any other credits, benefits, or transfer bonuses that come up. This will serve as their points and miles budget.
Obstacle deck: In a post coming out this Friday, we’ll be asking for your input to help create a deck of obstacles that represent your real-world travel obstacles. For example, if your travels always include your whole family of 4, we might add an obstacle card for only booking hotels that could accommodate 4. (Again, look for a post to contribute those ideas on Friday!)
Power-up deck: It can be hard to gauge just how difficult our challenges might be until our contestants are already in motion. So just in case we’ve made things a little too difficult, we’re including a power-up deck too. This will include cards designed to make things a little easier, like a “get out of surcharges free” card, for example.
Challenge criteria and scoring
During the challenge period, contestants will have these primary criteria:
- Travel to your two wild card destinations, then end in the assigned final destination, arriving at each destination in time for a pre-scheduled livestream check-in.
- Your points and miles budget will have to come from the wild card credit cards you’ve drawn, giving you access to any bonuses, credits, benefits, and transfer bonuses available.
- You must try to satisfy your obstacle wild card’s limitations for your trip.
Stephen and I will then score them points for the following “WILD” metrics:
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- W — Wallet-friendliness: How inexpensive was your trip?
- I — Ingenuity: Did you demonstrate ingenuity, using unique, interesting, or advanced techniques of the trade?
- L — Luxury: Did you demonstrate luxury throughout your trip?
- D — Duplicability: Would the elements of your trip be something another person could reasonably duplicate?
What happens next?
- On Friday, we’ll publish a post asking for your help designing our obstacle wild cards. Be sure to include anything you think accurately represents your own travel parameters!
- On September 9th, our contestants will go live to draw their wild cards, determining the parameters of their trips. In this livestream, we’ll also reveal the location of the final common destination.
- Just a few weeks later, our contestants will depart!
- 2 days after take-off, we’ll have our first live stream check-in to discuss and judge the Destination travel.
- 2 days later, we’ll have our second live stream check-in to discuss and judge the Destination 2 travels.
- 2 days later, we’ll have our final live stream check-in to discuss and judge the final travels, revealing the final winner of the Wild Card challenge!
Technical rules and questions
Your questions always help us refine the rules and technicalities, so please comment below with any questions about this challenge!
Follow along
- Blog posts: We will post regular challenge updates to this blog. If you haven’t already, please subscribe to our email newsletter.
- Instagram: Instagram is the best place to keep up with the action in close to real time. Make sure to watch our stories! Follow Frequent Miler on Instagram here.
- YouTube: This is where we’ll do livestreams for each live check-in. In these check-ins, we encourage you to comment along. You never know – you could even influence the judges’ decisions as they’re scoring! Subscribe here so that you’ll be notified when we go live.
You can watch the coffee break episode where this challenge was announced below.
Coffee Break: The 2026 Team Challenge: Wild Card!
Watch here:
Or listen here (or click “Follow” on the player below to select your preferred podcast app instead):
(00:41) – What are the FM team challenges
Learn more about past challenges here: https://frequentmiler.com/annual-team-challenges/
(01:24) – Why do we do these?
(03:39) – Who’s participating this year
(04:41) – Introducing: The Wild Card Challenge
(08:08) – High-level about this challenge
(10:48) – How do the contestants feel?
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Music Credit – “Ocean Deep” by Annie Yoder
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Maybe not for this challenge but at some point I’d like to see a trip where they had to consistently find rooms with 3 beds (not including a sleeper sofa). I often travel with two friends and this is a major pain point for us. Have even had to resort to (gasp!) cash in some cities simply because we couldn’t find a place that would sleep all of us at once.
Who gets to draw from the cards first? Greg cause he’s the boss? This will have an impact on the outcome. Draw straws first to see who draws cards first? LOL
For destination 1 we’ll probably do contestant 1, contestant 2, contestant 3, and then for destination 2 we’ll do contestant 3, contestant 2, contestant 1.
For credit cards, we might do contestant 1, 2, 3 for the airline card, contestant 2, 3, 1 for the hotel card, and contestant 3, 1, 2 for the transferable points currency card.
For the challenges and power ups, we’ll probably to 1, 2, 3 for one of those and 3, 2, 1 for the other.
All that said, it’s not going to make too much of a difference because they’re going to be picking their wild cards at random. The cards are all going to be face down, so there isn’t really any proper advantage to picking first versus last – it’s not like the 3 Cards, 3 Continents challenge where we got to pick specific cards that we wanted.
I think it would depend on the number of cards in the deck and the variance in value. If N is small (say, 6 cards) and V is high, the quality of the deck after 1 or 2 cards at drawn could be significantly different
Yeah, but if it is a random draw it won’t matter. Each participant has equal probability of getting each card.
I’m assuming they’re removing each card as it’s drawn.
If so, and if you imagine a three-card deck where the cards have values of 10, 1, and 1 you can see that the first to draw has a 33% chance of drawing the value 10 card, the second to draw has a 22% chance of getting that card, and the third to draw has an 11% chance.
If they return drawn cards to the deck, you’re correct. And if there are enough cards in the deck, or the variance is lower, the difference shrinks rapidly.
Maybe we are imagining this working differently because I don’t understand where your percentages come from. If you have a deck of three cards, shuffle them thoroughly, and deal them out to three people each person has the same chance of getting the 10, or 1/3 for each player. The first person has a 1/3 chance of getting it. But 2/3 of the time they won’t get it, and then the second person then has a 1/2 chance of getting it for a total probability of 2/3 * 1/2 = 1/3 that the second person gets the 10. If the first person has 1/3, and the second person has 1/3, then the third person has 1 – 1/3 – 1/3 = 1/3.
Think of it another way. The cards are shuffled and dealt to the three people face down. At that point each player has 1/3 change of getting the 10. The odds don’t then change based on the order you turn the cards face up.
Once you shuffle the cards and fully randomize them the odds are set. It doesn’t matter what order you deal them out because each card is random.
One obstacle idea is only using walking, biking or public transportation to get around: no private cars, taxis or ridehail vehicles allowed.
Bonus points if you can figure out UK railcards.
Curious how the points currency will work? For example, what if Greg gets Citi or Capital One?
Most (or all – I haven’t double checked) Citi and Capital One transfer partners are partners of other transferable points programs, so he could just transfer from those.
Except AA, but Greg currently has plenty of AA miles so that shouldn’t be a problem.
no EVA then so dont send him to TPE!
For obstacle, similar to Mike below, might limit outbound flight to leaving on Friday, Saturday or Sunday. Otherwise, if I’m a contestant, I’d go ahead and book cancellable long-haul flights now to Europe, Asia and South America in biz knowing when they will be traveling.
This was mentioned on the podcast, but I love the idea of requiring either a suite booking or a room with a physical separation from an area for kids to sleep. This is a requirement for us now traveling with small kids who go to bed early and parents who don’t sleep well with the kids in the same room.
Another kid-related obstacle – contestant must plan activities that will allow and appeal to kids under a certain age (~6).
Due to the timing of the challenge, we can’t really specify which day of the week they depart as it’ll have to be within the actual challenge timeframe in order to make the preset livestream timings.
Although they know when they’ll be leaving, they don’t yet know which country they’ll have to fly to first, nor which points currencies they’ll be able to book with as that’ll all depend on which cards they draw in early September. They may also not have enough points/miles in order to book in business class. There’s therefore not really any way for them to reasonably book any flights now; once they’ve drawn their various cards next month though, they’ll be able to start booking immediately.
Looking forward to it! An ideas for power-ups: being able to use AmEx Platinum’s (or another credit card’s) airline incidentals credit in addition to the “normal” budget (just for accounting purposes, since IRL the contestants might have pre-selected a different airline than the one they’ll be flying with). Similar for Resy credits or some such. (OTOH, the Chase restaurant credit, whatever its name, might be considered more of an obstacle! 🙂 )
What is the cash budget for the challenge? Leaving it open-ended with only the constraint of being penalized in the wallet-friendliness category may make it too easy to spend more cash to get better trips. If there won’t be a set cash budget like in prior challenges, maybe pre-specifying the thresholds by which the W category will be scored (eg, 8 points if <$750, 4 points if <$1000, 0 points if <$1250, otherwise -4 points) will at least introduce concrete budgeting into the challenge.
This is a good question!
I think it’s reasonable that if they’re only “counting” the cost of hotels and flights that the cash budget would be $0.00. If they weed out the lousy offers from the decks it’s reasonable to expect that each contestant will start with 80-100,000 airline miles, 100-150,000 hotel points, and 100,000 + transferrable points. This is a much larger set of miles and points that in previous competitions. Experiences / meals don’t seem to figure into the judging of this particular competition, so whatever they spend on those doesn’t matter. The only curveball would be some large expenditure (like a long-distance cab ride) that unlocks a better air routing or hotel option and that could be handled by the judges penalizing the “W” category.
Although airline co-pays and hotel chump-charges (like resort fees) probably do need to be considered.
Note that many transferrable cards these days come with some kind of hotel credit.
Also, will cash-back cards be included in the decks?
We don’t have any cashback cards in the decks
We’d discussed whether to have a cash budget for this particular challenge and ultimately decided against it.
However, the contestants know that Carrie and I tend to be more frugal when it comes to travel and we’re the ones judging the challenge, so they know they can’t splash out thousands of dollars on taxes/fees for award flights unless they want to be severely dinged in the wallet-friendliness category.
That’s an interesting idea about having points listed ahead of time based on how much they spend as that could give them a better idea about how strict they want to be with their spending. Carrie and I will have to discuss things to decide if that’s how we want to proceed.
You invited questions, so here goes. . .
How do the destinations work? What destinations are in the deck? All continents? Are there any controls for making sure that one contestant is not unduly favored or disfavored by the luck of the draw (eg, Greg gets Paris and Rome, Nick gets Capetown and Seoul). Or is that part of the “wild” aspect?
From the podcast it sounds like you’ve decided on the third destination already, and will inform the contestants at the kickoff meeting? Did you consider not making the decision until after you know the destinations the contestants drew? I’m thinking of the case in which one of the contestants is particularly well-placed to get there. And, perhaps, not notifying them of the destination until they’re in transit?
On the card draws, each contestant will get one hotel, one airline, and one transferrable card? Have you considered a limited number of card exchanges where the contestant can replace a card with another one from the same deck? Say, one or two options to trade a card for a same-deck card? This could be used at draw time, or during planning, or even during the trip (to trade out an obstacle card, for instances). Similarly, did you consider allowing contestants to trade cards with each other?
What’s the universe of credit cards that will be in the deck? It would be a shame if one contestant got the Alaska Summit card and someone else got the American MileUp card.
Are obstacles and power-ups drawn at the kick-off meeting or during the trip? How many of each? Can the judges “assign” obstacle / power-up draws during the trip as rewards or penalties, or to help rebalance the game?
Are obstacles intended as constraints (eg, you must book on a flight that would allow 2 pax, you must use only direct flights) or as “something went wrong” (your next flight is cancelled)?
I can see a contestant getting hosed royally depending on the destination if its not well suited for the airline, hotel and transferrable currencies they end up with.
How do the destinations work? What destinations are in the deck? All continents? Are there any controls for making sure that one contestant is not unduly favored or disfavored by the luck of the draw (eg, Greg gets Paris and Rome, Nick gets Capetown and Seoul). Or is that part of the “wild” aspect?
Without giving too much away right now, we have a number of destinations grouped together for Destination 1 and a number of destinations grouped together for Destination 2. To an extent, things will be luck of the draw – there are destination combos where they’re going to be easier to get to, with some combos where it’ll be harder. That’ll be part of the wild card element, but we have set it up in a way that it should be reasonably fair for all three of them – you’ll see why that it when we do the drawings next month.
From the podcast it sounds like you’ve decided on the third destination already, and will inform the contestants at the kickoff meeting? Did you consider not making the decision until after you know the destinations the contestants drew? I’m thinking of the case in which one of the contestants is particularly well-placed to get there. And, perhaps, not notifying them of the destination until they’re in transit?
Some Destination 2 locations will certainly be a little easier to get from for Destination 3 than others, but it should still be achievable for all of them no matter where they end up for Destination 2. We picked their final meetup destination for a reason that we’ll reveal during the livestream.
On the card draws, each contestant will get one hotel, one airline, and one transferrable card? Have you considered a limited number of card exchanges where the contestant can replace a card with another one from the same deck? Say, one or two options to trade a card for a same-deck card? This could be used at draw time, or during planning, or even during the trip (to trade out an obstacle card, for instances). Similarly, did you consider allowing contestants to trade cards with each other?
That could potentially be one of the power up cards they draw.
What’s the universe of credit cards that will be in the deck? It would be a shame if one contestant got the Alaska Summit card and someone else got the American MileUp card.
We’ve picked cards that all award a decent number of miles/points – we’re not going for cards that have things like 25K welcome offers. That said, there will inevitably be some cards that have better offers than others. That’s another wild card element – one contestant could get wildly lucky with the cards they pick and someone could get unlucky, but even with the worst selection of cards I imagine that they’ll be able to put something together. If someone got particularly unlucky cards, that could mean they’re able to earn more points for ingenuity due to necessity being the mother of invention.
Are obstacles and power-ups drawn at the kick-off meeting or during the trip? How many of each? Can the judges “assign” obstacle / power-up draws during the trip as rewards or penalties, or to help rebalance the game?
Obstacle and power up cards will be drawn during the initial livestream where they pick destinations and credit cards. I don’t know if we’d assign additional cards to balance things out, but it’s a wild card challenge, so who knows what wild cards we come up with during the challenge 😉
Are obstacles intended as constraints (eg, you must book on a flight that would allow 2 pax, you must use only direct flights) or as “something went wrong” (your next flight is cancelled)?
Obstacles will be some kind of factor that’ll get applied to their entire trip in some way and which, for the most part, will affect the booking process before their actual travel (although there are some challenges we’ve come up with that’d affect their journey itself; whether we go with those will depend on what suggestions readers have when we solicit those suggestions).
For example, if someone gets a persona such as ‘Always travels with a partner, so you have to find award availability for two people’, that would apply to all three flights they have to take and they’d have to be able to show in some way that there was availability. However, we wouldn’t add artificial constraints on top of that, such as also needing to only book nonstop flights, because with some destinations that might simply not be an option.
For obstacles I think must leave after regular work hours i.e. first flight leaves after 7pm. I often find flights that leave mid day which would require an extra day of PTO.
I have a couple ideas for power ups: Double dip one of your cards annual credits or upgrade a card to gain credits for a higher annual fee version of the card.
Those are some great suggestions 🙂
Must stay within a 15 minute walk from the center of the city and have to walk everywhere except to/from airport (I often find that the chain hotels in Europe are not centrally located).
Here’s some real world obstacle scenarios:
-the p3: must gate check and travel with a stroller
-the split: ground connecting between NYC, London, or other multi airport cities
-the downgrade: can’t book first/business cabin for long haul
-the unknown: must book using a program they’ve never used before
-the I should have carried on only: airline lost your luggage, acquire a new suitcase and clothes at your first stop
-the weather delay- must reroute flight on the day of
haha love the stroller idea
Regarding the stroller idea specifically, we only ever gate checked a stroller for one trip (I think) despite traveling extensively with stroller-aged children. It only took that one (or maybe two?) trips to realize that it made far more sense to buy something collapsible enough not to need to be gate checked.
Not discouraging ideas at all, just commenting to say that’s not an obstacle I would recommend facing if you can avoid it – and there are products on the market that make it avoidable. I’m also not saying that we won’t use this idea – but, to me, this is like requiring that a contestant only travel with luggage that doesn’t have wheels. It can be done and it might be entertaining, but in real life, I’d not recommend that!
With regards to ‘the downgrade’, Carrie and I had come up with an almost identical obstacle based on the persona of a frugal traveler who never books anything higher than premium economy due to wanting to conserve their points.
We had that on the list for a long time, but removed it the other day as we realized that if one of the judging components is luxury, it’s not really fair to force them to not book luxury.
That said, perhaps there’s a way to include your downgrade suggestion in another way…
Love it
Sounds great. I particularly love the duplicability.
I am hoping the destination deck will incorporate the 5 filming locations of the movie “The Odyssey”.
Throwing out an obstacle for the deck: starting from a non-hub Midwest home airport without direct international flights. I feel like the guys already deal with this somewhat (Greg from Detroit and Nick from rural New York), but requiring the cost of positioning no matter what and having to figure out cheapest way to do so is a realistic obstacle for lots of your readers.
Ooh, I like that idea
I nominate CAK.
This is a great idea. I almost feel like an origin deck would be a fun addition. You could do one card for what Megan suggests, one for a hub captive like ATL or DFW, and one for a competitive hub like NYC or LAX (maybe SEA or SFO?). It would be especially fun to draw something like ATL origin but B6 credit card.