How Carrie & Stephen will score the 2024 Frequent Miler challenge (Flying by the Seat of our Points)


In less than three weeks, Frequent Miler’s annual challenge for 2024 will kick off: Flying by the Seat of our Points. This year, we’re testing our team’s skills with last minute travel. Greg, Nick and Tim will each have to book last minute travel to three different destinations assigned just 48 hours ahead of time by Carrie and me.

For Stage 1, they’ll be meeting up together at a certain location in North America. For Stage 2, they’ll head their separate ways to different locations elsewhere in the world. For Stage 3, they’ll meet back up in another mystery location.

Greg shared more about how the challenge will work in this post, so be sure to check that out for greater detail. For now though, I wanted to go into a bit more depth about how this challenge will be scored.

Flying by the Seat of our Points - Last Minute Travel Challenge points scoring

My wife and I are currently in the process of driving up to Alaska for this summer, returning in about two months time. Taking more than a week out of that for the challenge would detract too much from our Alaska plans, so I made the decision to sit out the travel element of the challenge. I’ll still be involved in this year’s challenge though because Carrie and I have been scheming for weeks – if not months – to make Flying by the Seat of our Points as fun – yet challenging – as possible.

In addition to being the ones planning where the guys will be going and what they’ll be doing, Carrie and I are in charge of scoring. There’ll be three main ways Greg, Nick and Tim can earn points – flights, accommodation and activities.

Flight Scoring

For flights in each stage of the challenge, there are up to 6 points up for grabs – up to 3 points for value and up to 3 points for experience. For each of those two elements, we’ll award 3 points for the person we deem to have done the best, 2 points for second place and 1 point for third place.

As you can tell based on those metrics, what we’re primarily looking for is luxury/comfort combined with value. Flying Emirates First Class would be awesome from a luxury perspective, but would come at a high cost in terms of both mileage and taxes/fees. Flying in economy would use fewer miles, but would come at their own expense when it comes to comfort.

Emirates First Class
Emirates First Class

Although we’re awarding points based on value and experience, there are many elements that could come into play when assessing their flights. We’ve therefore come up with a list of factors that will affect how we award points for their flight bookings. This isn’t necessarily a comprehensive list, they’re not in order of priority and we’ll weight each factor differently, but this is what we’ll be looking for:

  • Value
    • Good CPP (cents per point) value (e.g. 100%+ above RRV (Reasonable Redemption Value); if someone’s CPP is below the RRV, they’ll likely get dinged)
    • Low taxes & fees
    • Fewest miles redeemed
    • Using airline miles/points already in account & not needing to use transferable points
    • Using a transfer bonus
  • Experience
    • Economy vs premium economy vs business vs first class
    • Nonstop flight
    • Quality of food
    • Quality of service
    • Comfort/spaciousness of seat
    • Flying on a carrier they’ve never flown with before
    • Window seat with direct aisle access
    • Amenity kit
    • Best airline lounge they’re eligible for based on their flights alone
    • Luxury (this would be partially accounted for with the economy / premium economy / business / first class factor and other elements above, but this could also account for someone traveling on a much better business or first class product than other participants.)
    • Well-priced Wi-Fi with good connectivity

Some of those factors will be more key when flying to their destinations for Stages 2 & 3; for their Stage 1 flight to the departure location in North America, comfort and cost will be the main things we look at.

It’ll be very interesting to see what award flights they’re all able to book. While the nature of last minute bookings means they might be very constrained with their options, some airlines open award availability at the last minute and so it might be possible for them to snag an award that’s not normally easily bookable ahead of time.

I’ve a feeling this element of the challenge could be as hard for me and Carrie to score as it will be for the guys to find the best flight options for them. For example, one person might find a nonstop flight lasting 7 hours, but where they’re flying in economy. Another contestant might book a wonderful business class product, but it requires 20 hours of travel time with three segments, while the third books business class flights requiring 2 hours of travel but with only two segments and the opportunity to take a free tour of their layover city. Which is the better experience?

For me personally, in real life I might pick the economy flight as I’d rather just get to my destination with as little hassle as possible. That said, if all three flights for the second option listed above were in Qatar Qsuites, I might be willing to suck up the much longer travel time and multiple segments for the significantly more pleasant in-flight experience. The third option might appeal too if the flight times were convenient and the layover city was one I’d be interested in visiting.

Center seats in Qatar Airways Qsuites

Accommodation Scoring

Similar to their flights, for accommodation bookings there are up to 6 points up for grabs – up to 3 points for value and up to 3 points for experience. For each of those two elements, we’ll award 3 points for the person we deem to have done the best, 2 points for second place and 1 point for third place.

These points will only be earned for the hotels they book for Stages 2 & 3 though; Carrie and I have already booked them a hotel for where they’ll be meeting up in North America for Stage 1 as they’ll all need to be at the same property for the Ask Us Anything livestream that evening where they’ll find out their first international destinations.

Similar to how we’ll assess their flight bookings, there are all kinds of factors that could come into play for how we’ll award points for the hotels they book. Again, this isn’t a comprehensive list and it’s not in order of priority, but it gives an idea of what we’ll be looking for:

  • Value
    • CPP (cents per point) being at least 50% above RRV (they’ll get dinged if the redemption is less than the RRV value)
    • Using $200 Amex Platinum Fine Hotels & Resorts (FHR) credit + no more than $100 extra after taxes and fees
    • Using free night certificates
  • Experience
    • Access to a club lounge
    • Luxury
    • Utilizing status
    • A suite with a separate bedroom & living room
    • Booking directly into a suite
    • Getting an upgrade
    • Excellent view from their room
    • Fantastic welcome amenity
    • Rooftop bar
    • Cool room/suite
    • Unexpected/uncommon features (e.g. washer/dryer being in room)
    • Some kind of free food and/or drink available outside of things like coffee in the lobby, breakfast, FHR benefits, lounge access, welcome amenity, etc. (e.g. Kimpton offers a free wine hour, some Strawberry Hotels and Choice hotels in Scandinavia provide evening meals, etc.)
    • Close to designated landmark (this will be a factor for Stage 3 only)
    • View of designated landmark from their room (this will be a factor for Stage 3 only)

With so many factors that can go into making for a comfortable / interesting / luxurious / good value stay, this could be another tricky one for me and Carrie to judge. For example, someone who has both Diamond and Ambassador status with IHG who books a beautiful InterContinental using a 40k free night certificate that can’t be topped up will likely have made a great redemption.

InterContinental Lyon - Hotel Dieu
InterContinental Lyon – probably not a property you’d be able to book with a 40k free night certificate

However, someone else might find a luxurious hotel in their city that can be booked through FHR for less than $200 (thereby having no cost after their Amex Platinum credit). They might get a significant room upgrade, plus they’d receive complimentary breakfast, a $100 property credit, etc. – another great booking option.

The third person meanwhile might find a Marriott property that can be booked using one of their free night certificates. If they applied a Nightly Upgrade Award to obtain a massive suite, had complimentary breakfast and lounge access courtesy of having Platinum or Titanium status and received a generous and unique welcome amenity, that could be in the running for best hotel booking for that stage, although by splitting out points being earned for value and for experience will hopefully make it a little easier to judge.

Another unknown at this stage is how many hotels we’ll need to take into account when awarding points. The plan – depending on flight timings both in and out of a city – is for Greg, Nick and Tim to stay two nights in the same location for Stage 2 and two nights in the same location for Stage 3. If they find multiple great accommodation options, they could potentially decide to book one hotel for the first night and a different one for the second night. If all three of them did that, that’s six hotels to consider for each stage.

Challenge Scoring

While scoring for flights and hotels will be somewhat subjective, we’ll have a far easier time awarding points for the challenges at all three stages.

For Stage 1, Greg, Nick and Tim are each going to have the same, solitary, challenge. We’d originally discussed having some kind of destination-based challenges lined up where they could do some activities in that area. However, it might be that one or more of the participants won’t arrive in the Domestic Convergence city until the afternoon, with the Ask Us Anything livestream taking place that evening. That won’t give much time for them to explore their destination and make it back to their hotel in time, so we have a fun little activity planned that won’t take much time to complete. It’ll be easy to rank the three of them from first to third, so first place will earn 3 points, second will earn 2 points and third place will earn 1 point.

Now, they’re the kings of the swingers, oh, the Maldives VIPs…

For Stage 2, each contestant will be given a set of three challenges unique to both them and their location. If they complete all three challenges, they’ll earn 3 points. Complete two to earn 2 points or only complete one to earn 1 point. (And, heaven forbid…earn 0 points if you complete none.)

For Stage 3 where they all meet back up in the same city, there’ll be three challenges, but in the form of one challenge per person. Carrie and I will then award points based on who we deem to have done the best with the activity they plan. Similar to other scoring, the best activity will earn 3 points, next best will earn 2 points and third best will earn 1 point.

Bonus Point Opportunities

Based on the earning opportunities listed above, there are up to 39 points up for grabs:

Stage 1

  • Flights = 2-6 points
  • Challenge = 1-3 points

Stage 2

  • Flights = 2-6 points
  • Accommodation = 2-6 points
  • Challenges = 1-3 points

Stage 3

  • Flights = 2-6 points
  • Accommodation = 2-6 points
  • Challenges = 1-3 points

The nature of the scoring will likely mean that all three participants will have fairly close scores by the end of the challenge. In addition to those standard points, Greg, Nick and Tim will have opportunities to earn bonus points.

We don’t have set parameters for what will specifically earn bonus points, but as a former United States Supreme Court Justice might have explained if they were responsible for doling out bonus points for this challenge:

I shall not today attempt further to define the kinds of material I understand to be worthy of bonus points, and perhaps I could never succeed in intelligibly doing so. But I know it when I see it.

For example, one person might book a hotel that blows away the bookings of the other two contestants in one way or another. Having them earn 3 points for an experience or value factor while the second placed person earns 2 points might not provide enough differentiation in scoring.

Similarly, someone who manages to book a low redemption cost, high-luxury flight might deserve more of a point difference than a maximum of two points. Another example would be if their flight(s) have availability for at least two people. While this isn’t necessary for the purpose of this specific challenge, if they could show that what they book would be possible if they had one or more other people traveling with them, that might be deserving of bonus points, especially if they were able to do that for all three stages.

Another potential way to earn flight bonus points would be for the coolest booking. This would be completely subjective, but it could be through travel on an unexpected airline, an intriguing routing (e.g. 5th freedom flight), a layover with a free city tour, etc.

When it comes to challenges, perhaps a contestant will deserve bonus points for doing theirs with flair. For example, let’s say we gave the following challenges to someone for Stage 2:

  • See the city from above
  • Do something you’ve never done before
  • Find a local person to do an activity with

Someone might fulfill those requirements by having a drink in a rotating bar at the top of a skyscraper, going whitewater rafting and doing a free guided walking tour respectively. That would be interesting, but not necessarily worthy of a bonus point. However, if they booked a tandem skydive, that could satisfy all three challenges within one activity, while also being fun and exciting – worthy of a bonus point.

We don’t have a specific number of bonus points to award – it’ll all depend on how the three guys manage to impress me and Carrie with their bookings and activities.

When Points Will Be Awarded

At each stage, we’ll be announcing rankings and awarding points (both standard and bonus) during a livestream on YouTube where all five of us will be there.

  • Pre-Departure – Monday June 3 at 9pm ET. This will be where Carrie and I let the guys know which North American city they need to head to for Stage 1.
  • Stage 1 – Wednesday June 5 at 9pm ET. We’ll be awarding points for their flights from their home airports to the Domestic Convergence city, as well as awarding points for their first challenge.
  • Stage 2 – Friday June 7 at 2pm ET. We’ll be awarding points for their flights from Stage 1 to Stage 2, their hotels at Stage 2 and for any Stage 2 challenges they’ve managed to complete by that point.
  • Stage 3 – Monday June 10 at 9pm ET. We’ll be awarding points for their flights from Stage 2 to Stage 3, their hotels at Stage 3 and for any Stage 3 challenges. We’ll also award any final bonus points which will enable us to announce the winner of Flying by the Seat of our Points during this livestream.

In addition to us awarding the points, viewers will have a chance to make a case in the livestream comments at each stage for whether bonus points should be awarded for any of the contestants.


Are there any other factors that you think should be accounted for when we’re scoring the Flying by the Seat of our Points challenge? Let us know your ideas in the comments below.

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After watching the IG Stories for Stage 1 and Tim & Greg Day 1 journals I think Greg currently has some negative points in the Value Category or just 1 point.

My reasons:

  • First. One of the rules is to use the points that they have in their inventory first and try to avoid or use less transferable points. Greg did not have Turkish Points, so he transferred points either from Bilt or Citi to Turkish.
  • Hotel & Car Rental – Greg will fly on June 4, 2024, and he will need to get a room to sleep in LA, rent a car and go back to the airport, and wait the 30 minutes penalty (Penalty rule for landing before 3:00 pm on 6/5/24). So there’s extra cost on Hotel Points/ Certificate plus Car Rental expenses/points.

If we want to be fair with the other contestants the additional points on Hotels or the value of Hotel Certificate will need to be considered when judging the value category.

In the Experience category – Greg will score 3 or 2 points in Experience for flying a direct Business Flight.

This is my humble opinion for Stage 1.


So looking forward to hearing every day what’s happening. I reported every day where you went and all the mishaps to my (non interested in points) husband who was interested in the trip. I learned things from the trip but it was super entertaining too. I’m not so much interested in who wins as where you go and what happens. I will never forget the house your team rented last time in the Philippines!


I’d start looking for flights to DC if I were Greg/Nick/Tim…


Mexico City, Toronto, or Montreal. My money is on Mexico City (as equivalently difficult for all three players to reach).


Why limit accomodation points to only FHR credit? Citi/Strata Premiers credit is even harder to use effectively.


Don’t know if it’s in the budget, but I’d love to see a separate page at Frequent for the contest. One column for each player with a recent selfie from the trip, their current score, their current location and task, and their log entries under that. Keep it fresh with frequent updates.


My suggestion is to repackage that content (amost all of which you’ll already have) onto a separate competiion page. I bet, at least while the contest is ongoing, that page would get a lot of user engagement.


Really looking forward to this! We usually book 1-3 months out but we’ve changed several flights within 48h of the trip when something great opens up (best ones – AA from JFK to HND in flagship Business via LAX for 60k x2 the day before our trip or Lufthansa first from FRA to JFK x2 48h before) so interested to see what you guys find.

Best thing about these challenges is what you uncover! I’m not bothered by the lack of budget because I know that you all, like me, will want to find the best combo of cost and quality and won’t rest until you do.


I’ll follow along but this challenge like the last year’s challenge aren’t very challenging when there is no cap on points/miles used. Scoring is irrelevant. I don’t think most readers have a massive supply of a variety of points at their disposal. You could repeat the original 40k challenge each year and that would be exciting.


As someone with a massive supply of a variety of points at my disposal, I award your comment six points.


I’d think that most of your readers are not booking last minute trips, so additional points for Greg, Nick, and Tim could reflect the following:

Flights – if the flight they pick either a) consistently shows last minute award availability (the more people the better) or b) can be booked farther in advance (3-9 months for example, and for multiple people)

Hotels – sometimes last minute hotels can be hard to find or expensive. It might be applicable to more people if they show that even if a hotel is sold out right now, someone could use a FNC or FHR credit in the future for good value if this was planned farther in advance.


Speak for yourself. I mostly book last minute. Rather than trying to fit their contest into your travel style, consider using it as a learning experience. Many great deals are only available last minute, let the team show you how to do it!

I used to completely resist the idea of stop-over visits but have changed my mind, in part from seeing how Greg and Nick have leveraged them during some of the competitions.


I’m not changing the structure of the challenge – these are bonus points, so I’m not sure why you’re upset.

I know that many great deals are available last minute, which is why I’m trying to make this challenge harder. It might be easy to get a good comfy seat to Asia last minute, but finding it also available months in advance adds challenge.

There’s nothing wrong with them showing how to do a last minute booking – that’s amazing. What’s more impressive is if they uncover something that is actually more widely available, hence the bonus points.

Nick Reyes

I always say that these challenges are less about showing you something specific to replicate and more about demonstrating techniques we employ to meet the challenge at hand.

To your point about booking in advance, we’ve several times now (with 40K to Far Away, 3 Cards 3 Continents, and Party of Five) done challenges where everything we booked was booked 3-9 months in advance — and I don’t think I booked anything that wasn’t available for more than one person (and Greg booked for two people during 3 Cards 3 Continents).

This challenge is obviously going to be a different one that just isn’t at all about what’s available 3-9 months in advance. We’ve done that with previous challenges and I’m sure we’ll do it again, but this time around that’s not the objective. We’re intentionally doing something completely different here.

Still, I imagine that the tools we use will in some ways be applicable even when booking far in advance, so I think you’ll get something out of it even if you aren’t someone who books or rebooks travel close-in. To that last point, one thing that I often do is book something far in advance with a hope to cancel and rebook if something better shows up last minute — so I see value in showing people the last minute stuff even if they primarily book far in advance because one of the benefits of many kinds of award travel is that many awards are freely or cheaply refundable if and when you find something more desirable.


Understand the time restriction, but would be really cool to see more than 1 “divergent” middle destination. I think that 2nd stop is going to be the most interesting


These contests are always too short for me, the viewer. I’d love to see an extra stop and/or an extra day on each place for more elaborate activity challenges. But we have to recognize that it’s already a major commitment for the participants as well as a significant cost for Greg.


This really needs to be thought out carefully by Stephen and Carrie. There are plenty of destinations where there might just be few waus to get in and/or out, especially last minute, and thus high potential for duplication.


I would wager money that the entire team defined the boundaries around what destinations can be chosen. It definitely wouldn’t be fair if Greg got Mexico City – Paris – Cairo, Nick got Mexico City – Frankfurt – Cairo, and Tim got Mexico City – Coober Pedy – Cairo. I’m sure that the all the travel sections need to be “equivalent” in terms of direct flight distance, service by all three alliances, approximate number of flights, and distribution of flights between non-stop, one-stop, and two-stop.


Carrie & Stephen make sure they are going to places that do not have any Hyatt’s!


I’m hoping that cause Carrie will send them to someplace without hotels!


Looking forward to reports on your adventure in Alaska. And how will you drive to Alaska? I assume you will have to eventually put your car on a ferry.


If I understand my geography correctly, will you enter Alaska from the Yukon territory.


Which routes are you taking up and back? I’m curious if you considered taking the Alaska Marine Highway ferries in one direction? I drove from San Francisco to Fairbanks and back 20 years ago with some friends and had a great time. We took the Alaska Highway on the way up and the Cassiar on the way back. Unfortunately we didn’t have much time off work, so we did the whole trip in 2 weeks and put over 7,000 miles on a rental car…..your schedule seems much more appropriate


Well, I’m looking forward to following along! I’ve got a trip to Utqiagvik planned for September. On your way back, I’d recommend being sure to do the side trip to Stewart/Hyder between Dease Lake and Smithers.


Hyder is a weird geographical oddity in that it is an ex-mining town with only like 50 people located in Alaska just over the border from BC that only has access to the outside world by that road to BC. In addition to the novelty of it and the beautiful views on the drive (which you will get a lot of everywhere in Alaska), the big thing is that there is bear observation deck outside of town over the river that is one of the few accessible by car (as opposed to like having to fly to Brooks Camp in Katmai). If you are there during the salmon run, it can be an easy way to hopefully see bears salmon fishing.


I used to live in Anchorage and I still have family there! Be sure to eat at the Moose’s Tooth- it’s always busy but definitely worth it. Not sure if dogs are allowed inside but you could always do takeout and picnic somewhere.


Participation points? I suggest that you assign point values of 2-1-0 so the person in last place doesn’t get any points.

FM Fan

There are plenty of professional scoring systems where “losers” still get points assigned to them, like the “10 point must system” in boxing.