Flying by the Seat of our Points (Last Minute Travel Challenge)


Introducing Frequent Miler’s 2024 team challenge: Flying by the Seat of our Points! With this year’s challenge, three of us will compete to book last-minute travel. Within each of three stages, our judges will give us our assignments (where to go and when to get there) and we’ll have just a couple of days to make it happen. For example, perhaps I’ll be in Chicago on a Wednesday and will learn that I need to be in Morocco by Friday. My goal then will be not just to get there in time, but to book an awesome award flight to get there. While “awesome” is in the eye of the beholder, the idea is to get a combination of great value for my points plus a great and preferably luxurious flight. Similarly, I’ll have to find a great place to stay in Morocco and will try my best to get great value booking the hotel with points (or free night certificates, or whatever). In this challenge, the contestants will be flying separately, but if all goes well, we’ll meet up twice — somewhere in the world.

Team Challenges (Background)

Each year, Frequent Miler team members compete to outdo each other in researching, booking, and completing a trip that uncovers and highlights incredible opportunities available through points and miles. For example, in 2019 with the 40K to Far Away challenge, we competed to see how far we could go with just 40,000 points and $400. That year’s winner (yours truly) ended in the Seychelles after visiting Spain, Senegal, and South Africa. And in 2022, in the 3 Cards, 3 Continents challenge, we competed to see who could build the most amazing 3-Continent trip with just 3 credit card welcome bonuses. The 2022 winner (Nick) completed 3 continents in just the first two days of his trip when he visited the Egyptian pyramids in Africa and took a boat ride in Istanbul in order to visit both Europe and Asia. He went on to swim with sharks in Oman, zip-lined and jumped off of waterfalls in the Philippines, visited Santa Claus at the north pole, and capped it all with a spectacular viewing of the northern lights. Most recently, in 2023, we split into teams with the Party of Five challenge. Over a two week span, the Frequent Miler team travelled through Asia and southern South America. Team Tokyo (Stephen and Carrie) took us to the Philippines, Macau, and Tokyo. And Team SFO (Tim and Nick) took us to San Francisco, Santiago Chile, Buenos Aires, and Iguazu Falls. I was the judge in that competition, but after my scoring notes were stolen in Santiago I made the controversial decision of declaring a tie. This time, we won’t let that happen. Scores will be published publicly as we go along, and our judges will be safely at home (wherever home is for them at that moment).

During the May 8 2024 Ask Us Anything, we conducted a poll asking which of the past team challenges people liked the most. 3 Cards, 3 Continents was the clear winner with 55% of the vote. We’re hoping that the new challenge will be just as much fun, or better!

Flying by the Seat of our Points Challenge

This year, Nick, Tim, and I will be competing to see who best can complete a series of last-minute-travel challenges. At each livestream check-in we’ll be given new assignments telling us where in the world to go next and how long we have to get there (typically about 2 days). We’ll be scored based on our ability to get to each destination on time, the quality of our travels (e.g. the more comfort & luxury, and the fewer points spent the better), and our ability to complete mini-challenges along the way.

Carrie and Stephen will be the hosts, game masters, and judges for this competition. They’ve prepared destinations and mini-challenges which they’ll reveal as we go. The challenge will be organized into three stages:

Stage 1: Domestic Convergence

On Monday, June 3rd, via YouTube livestream, while each of us will be in our own homes, Carrie & Stephen will reveal our first destination — somewhere in North America. They will tell us which city to go to, which hotel to check into, and what time we must be there for a livestream check-in. They’ll also give us a mini-challenge of some sort to complete before heading off for our next destination. In this round, the hotel booking won’t be part of the score since we’ll all be in the same hotel.

Stage 1 Livestream Check-In: Wednesday June 5th at 9PM ET on YouTube. The contestants will be together for this one. During this livestream, our stage 1 scores will be revealed. Also as part of this livestream, our next destination will be revealed…

Stage 2: International Divergence

On Wednesday, June 5th at 9PM ET, via livestream, Carrie & Stephen will reveal our next destinations. This time, we’ll each go to a different place. They will tell us each, separately, which city to go to and what time we must be there for a livestream check-in. This time we’ll be free to book our own lodging… and that will be judged. They’ll also give us mini-challenges to complete before heading off for our final destination.

Stage 2 Livestream Check-In: Friday June 7th Time 2PM ET on YouTube. The contestants will now be in separate international locations. During this livestream, our stage 2 scores will be debated and then revealed. Also as part of this livestream, our final destination will be revealed…

Stage 3: International Convergence

On Friday, June 7th, via livestream, Carrie & Stephen will reveal our final destination. This time, we’ll once again converge to the same place. They will tell us which city to go to and what time we must be there for a livestream check-in. We’ll again be free to book our own lodging. We’ll be in the same city but not necessarily the same hotel. They’ll also give us mini-challenges to complete before departing the final location.

Stage 3 Livestream Check-In: Sunday June 9th or Monday June 10th Time TBD on YouTube. The contestants will again be together in the same city and we’ll make sure to do the livestream together in one place. During this livestream, our stage 3 scores will be debated and then revealed.

Final Winner

The final winner will be determined based on a combined total scores across each of the three stages.

Return Home

Contestants will return home on Tuesday June 11th. This part of the trip will not be scored.

Scoring Details

At the time of this writing, we’re very close, but we haven’t yet nailed down exactly how were going to keep score. The basic idea, though, is that we will earn points as we go along and the scores will be prominently posted so that everyone can see our standings at any time.

Once we’ve ironed out the details, Stephen and Carrie will post to this blog the scoring process and criteria they’ll use to judge our trips.

How to 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 here.
  • YouTube: This is where we’ll do livestreams at the start and end of each stage of the challenge. At each livestream we’ll summarize what we’ve done so far; you’ll have the opportunity to ask questions and (potentially) influence the judges; and we’ll all find out our next destinations and mini-challenges. Subscribe here so that you’ll be notified when we go live.

How to participate

If you’re interested in doing more than passively follow along, there will be a couple of ways that you can more proactively participate:

  • Help contestants via blog comments: Each contestant will have their own challenge diary blog post that will be regularly updated with what they’ve done so far, and plans (if any) for tackling the next stage of the challenge. If you have ideas that can help a particular contestant, then please post those ideas as comments within that contestant’s blog post. We’ll each be following these comments closely. No matter how knowledgeable we are about award booking, there will always be things that we don’t know (or may have forgotten) that can be the key to winning it all. You can choose whether to essentially join one person’s team by helping just within that person’s post or you can spread your wisdom across all of our posts. That’s up to you! But if you’re especially good at this, I encourage you to join Team Greg 😉
  • Help the judges determine our scores via livestreams: During each livestream check-in we’ll give an overview of the flights we booked and flew to get to the current location, including how much we spent in points and cash. Carrie & Stephen will have already determined who’s flights came in first, second, and third place for that stage. But, you can change their minds. If you disagree with the judges stance, we’d love for you to argue in the comments, for example, why Tim’s flight was better than Greg’s or Nick’s. If you can sway the judges, they’ll update the scores before the livestream ends.

Challenge Travel Gear

If you happen to be traveling during the challenge, maybe you’ll run into one of us. If so, please say hi! You’ll be able to spot us easily since we’ll be wearing our challenge hats (see above) and also carrying a matching water bottle.

If you’re interested in getting any of this for yourself, you can find the hat here and the water bottle here.

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
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Is everyone starting from they live (Michigan, upstate NY, Seattle)? If so, then the Domestic Convergence would almost have to be like Texas or Florida (or I guess some tiny airport somewhere) or somebody will have a pretty easy and boring.

Although, the description just says “North America” so maybe it could be CDMX or CUN, which would be cool.


The last second nature of this one should be quite entertaining and will lead to some redemptions you might not otherwise get with a more planned out trip (Lufthansa First Class anyone?).

Also with the timed nature I’d love to see write ups on back up flights that are booked to make sure you all get there by the deadline. I imagine most won’t get used so documenting what was in place would be very informative!


Should work pretty seamless considering it can be easier to find last minute availability via many transferable programs.


WOW! This is basically what I had imagined you might do this year. I can’t wait! These challenges are so valuable to observe… like watching the points & miles olympics!


This seems like about 1/4 of a challenge as compared to previous challenges that were much more involved and had more opportunities to entertain. Maybe this can be the first part and then the following month you can do another one?


Are the players allowed to leverage elite status and / or certificates or benefits they might have? If you have an AA SWU, for instance, can you use that to upgrade a cheap economy fare if available and get “credit” for booking a cheap business class flight?

I understand that the money component is coming from Frequent Miler, but how about the points? Can each player only use their own stash of points for booking, or can they “call down” points from some central pool?

If the answer to either of those questions is Yes, it would be interesting for the players to outline what they perceive as the strengths and weaknesses of their points and benefits “accounts” at the outset of the game.


I have the same question. Is everyone using their own stash of points/miles/certificates/etc? I love the idea of this and can’t wait to see what the team does. But in terms of judging and declaring a winner, it seems like someone may just get luckier than others with award availability or having the right currency at the right time. Does it matter how you acquired the points in the first place – it’s more impressive if booked with points earned ‘the hard way’ vs just finding an award and buying the points on sale, or someone lucking out with a good transfer bonus the others couldn’t take advantage of.


Love these and it always reveals new sweet spots

Ryan del mundo

Can’t wait! 40k to Far Away was my fav I think as I like to stretch my points, but they’ve all been fun, engaging, and informative!

As I often travel without a pre-set itinerary, I have a feeling this one will be my favorite challenge yet!


This is an awesome challenge idea. @Greg, can we make the Domestic Convergence available for Readers to join? It will be fun to meetup with y’all!!


I understand and you should prioritize the challenge!!

But if you can make it happen, it will be a mini-challenge for Readers to find last-minute flights to the Wednesday location haha 🙂

Phil Ridolfi

That would be fun! Great contest!


i hope this will add the challenge of last minute visa application (if it is even doable), despite the us visa can probably get you a lot of places visa free to begnin with 🙂

Ryan del mundo

Visas don’t play well with last minute plans. I had 3 weeks to get one from Thailand and due to bureaucratic snags, it didn’t get done. Maybe Nick can get stuck again in the Bangkok Airport (I still wonder what would have happened if he just left the airport!).

Nick Reyes

They wouldn’t let me leave — I had to show my boarding pass at a checkpoint to leave. That’s where I got stopped.


Wait, the judges will be at home. But Stephen is a judge? #NHJR

this will be fun,I like that you’re doing a domestic competition as for some of us, that’s the most common travel.


I agree will be really cool to see some good domestic redemptions in action, with the big 3 getting stingier on partner availability and some of the program revamps and devals we’ve seen. Maybe an interesting non-plane option makes the cut like an Amtrak first class seat or a BLADE ride? Or a smaller business class airline like JSX?

Last edited 15 days ago by Andrew

The hat is listed as private.


Good luck, travel safe, and let the odds forever be in your favor!


This is going to be so cool! I can’t wait to follow along. In fact, I want to replicate this to do with my friends!


Budget limitations in cash/points & miles?

Nick Reyes

Spend as little of the boss’s money as possible while having as impressive a trip as possible! For this challenge (booking last minute), it didn’t seem to make as much sense to have a specific budget since we’re at the mercy of what’s available at the moment when we find out the next destination. Instead, we’ve opted to keep it a bit more open because there’s not exactly a way to plan that out, particularly with no idea where you’re going next. But the goal will be to impress you, so I imagine we’ll all be looking for the best deals possible rather than looking to spend a million miles each.