Flying by the Seat of our Points: Last Minute Travel Challenge

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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. The goal will be not just to get to each place in time, but to book awesome flight and hotel awards. While “awesome” is in the eye of the beholder, the idea is to get a combination of great value for our points plus great comfort or luxury. In this challenge, the contestants will be flying separately, but if all goes well, we’ll meet up twice — somewhere in the world.

UPDATE: The challenge is done! And the winner is… Tim! This was Tim’s first time competing individually and he did an amazing job. Congratulations Tim!


For details about what happened and how we were scored, see the Challenge Home Page.

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 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: Monday June 10th 9PM ET 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

For details about how scoring will work, see: How Carrie & Stephen will score the 2024 Frequent Miler challenge.

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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[…] 2024 年团队挑战 按照我们的积分点飞行 通过一系列最后一刻的旅行挑战测试我们最后一刻的奖励预订技巧 由 Stephen […]

Sean

Greg, if you don’t mind my asking, how did you get to be 100K on Alaska? That is a very tall order for someone who lives in Detroit. You can put miles from any oneword member on Alaska, true, and you get bonuses for credit card spend, but any way you slice it that is still a tall order, particularly since you have status on other airlines too.

Andrew

I was hoping with a California destination that someone could highlight JSX airlines, an all business class airline flying semi-private jets. I’ve wanted to know more about potential sweet spots after seeing them mentioned by Gary Leff over at VFTW.

Turns out they fly to LAX! With a private terminal! With an ability to have a rental car waiting right for you! Landing at 3:10PM! …but not until Thursday June 6. Their Vegas to LAX route doesn’t fly tomorrow.

They do have routes to other LA area airports in Burbank and Orange County, not sure if the challenge stipulates LA area at 3PM or specifically LAX airport. But with traffic at that time of day venturing to another airport is probably a bad idea for the hotel race.

Could make for an interesting positioning flight on the way out depending on the next international destinations. They fly from the LA area airports to Dallas, Las Vegas, Phoenix (Scottsdale), Denver (Boulder), and San Francisco (Oakland).

Joe

It’s not luxury but JSX at Burbank also uses what was literally Amelia Earhart’s hangar in the 1930s.

Tyson

I live in L.A. and there is a lot of great fusion food. For instance the Cogi truck has Korean tacos! Might be able to hit several locations in one food! Also, I hope TMZ will be waiting for you at the airport. 🙂

Lrdx

Why do you think people on the West coast only wants to travel transpacific?

Mantis

For the meal challenge, I’d choose sushi. One of you is going to Asia for sure. And if you’re wrong, hey, there is some phenomenal sushi in LA which you get to enjoy, so there’s that.

Mike

Kind of disappointed with LAX being the first meet up spot. I feel like most novices in the game could easily find last minute flight to and from LAX. I was hoping for something more challenging that would involve connections and/or positioning to get to and from. Took a 60 second search on one airline site to find a biz class flight from Washington to LAX that arrives at 3:18pm on Tuesday. Not really much of a challenge. Or maybe IAD-MUC-LAX arriving at 3:15pm just to have fun.

LarryInNYC

While I agree the destination is a bit pedestrian (I was figuring on Mexico City, or someplace else in Mexico or Canada, at least until the language changed from “North America” to “domestic”) there’s still some competition to see who can squeeze both value and luxury out of this segment. And flying to LA is probably of more general interest than Leon, Mexico.

The fact that people (probably) won’t leave home until tomorrow morning neutralizes any location advantage Tim might have had and, indeed, the luxury options mostly involve traveling to the East Coast and flying one of the premium transcons from there. I think the luxury side of the competition may come down to a choice between AA Flagship First or JetBlue Mint if either are accessible with points at the last minute.

Mantis

I like it. Since the next destination is international and different for everyone, it makes sense for the first stop to be in a non-captive, international hub like LAX. Otherwise one would likely have a big advantage or disadvantage, depending on their respective next destinations. This way, whether their next destination is Europe, Asia, or South America, there are many options to consider. Do you really want all 3 to be fighting over who can book that last seat out of Des Moines?

Pierre

LAX can be tougher than other West Coast airports for last-minute availability so it will be interesting to see what they come up with

LarryInNYC

I find it hard to imagine the complexity in selecting the cities in terms of not unduly advantaging or disadvantaging one of the contestants.

Stephen Pepper

We have a reason we’d picked LAX as the first location. We’ll be explaining more in a future post once the guys know where they’ll be going after that.

Ian Maschal

My money is on one of the top ten furthest destinations from LAX. So
Maybe the Middle East or AUS.

LarryInNYC

Remember that for the next destination they don’t have to send the contestants even to the same continent. Some could go to Europe and some to Asia or South America, for instance.

Pierre

Tim will probably have to go somewhere farther to make up for being closer to LAX

Mark

“Welcome to LA, your hotel is the Hyatt… DFW”; first one there gets the king bed!

Stephen Pepper

Ooh, I like that twist!

Sco

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.

Andrew

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!

EruptingLoowit

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

Hall

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!

Leslie

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?

LarryInNYC

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.

don

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.