Frequent Miler’s next challenge: What should it be?


We recently wrapped up our 3 Cards, 3 Continents challenge where three of us competed to see who could build the most awesome 3-continent trip with the welcome bonuses from 3 cards.  That was just the latest of our Frequent Miler challenges.  In 2021, I gave Nick my Delta Global Upgrade Certificates (GUCs) with the condition that he bring me along and complete a series of individual challenges (earn elite status from the trip, collect KLM Delft Blue houses, get far outsized point value for stays, etc.).  In 2019 we competed to see who could go farthest with 40K points and $400.  Years earlier I challenged myself to earn enough points to stay on Richard Branson’s Necker Island.  Before that, I challenged myself to earn 1 million miles in 1 month.  And finally, in 2012, I challenged myself to visit New York City on $19 per day.

Now, the question is… what’s next?

Challenge Goals

The purpose for these challenges is to push the envelope of what can be done with points and miles.  By igniting our competitive spirits and constraining us to strict limits, we’re forced to innovate new techniques or test the limits of known ones.  The best example of this so far is when Nick was constrained to using Citi ThankYou Points for 40K to Far Away. This, led him to discover one of the best redemption opportunities in existence: US mainland to Hawaii for only 7,500 points.  In most cases, though, we learn (and share) by taking advantage of known award sweet-spots and push those to the limit.  That experience provides great insights for us so that we can better inform our audience about these opportunities.  My recent use of ANA’s Round the World Award is a great example.  This was already a well known fantastic sweet spot award, but none of us had ever previously booked it.  Now that I have, I understand its pros and cons better than I ever did before and so I’m in a great position to help others decide whether is is right for them, and to learn how to book it (expect a tutorial soon-ish, but for now see this post).

Challenge Parameters

We’d love to hear new ideas for challenges from you.  Ultimately we want to do something that ticks these boxes:

  • The challenge must be possible and practical.  We won’t challenge to see who can circumnavigate the world with 5K points – that’s not possible.
  • The challenge must encourage rewards innovation.  The idea should be to push us to figure out new and better ways to earn or use rewards, elite status, credit card perks, etc.
  • The challenge should be entertaining.

My Thoughts

The following thoughts are not requirements for the next challenge, but rather are my current preferences.  I’m sure I can be swayed to do other things if great ideas are suggested that don’t include what follows.

Repeat the Card Draft (or Something Similar)

The 3 Cards, 3 Continents Credit Card Draft was awesome.  I loved everything about it.  The idea for it originally came from a reader in response to a post like this one.  And I’d love to do it or something similar again.  Here was my original write-up about the concept:

We loved Jarrod’s idea of a fantasy draft for selecting who gets which points and we’ve taken it a step further: we’ll be picking from real current welcome bonuses.  Whatever welcome bonuses are on our Best Offers page when the draft begins will be fair game.  Once a card bonus is selected, it’s gone.  The next players cannot pick it.  We won’t really be signing up for cards.  Instead, the cards we pick will define our points & miles budget for the challenge.

Our budget begins at draft time.  We each have a $1,000 budget for our travels, including first year annual fees.  So when the first player picks the Platinum 150,000 point offer, for example, that card’s $695 annual fee will count against the player’s $1,000 budget and leave him with only $305 left.  He’ll have to pick the next two cards very carefully!

We will also be limited to $15,000 credit card spend.  Most credit card welcome bonuses require lots of spend in order to earn the bonus.  In our made-up scenario, we have exactly $15,000 of unbonused spend available.  We can’t go above that.  So, for example, if someone picks the Chase Ink Business Preferred 100K offer which requires $15K spend, their next two picks will have to offer bonuses with no spend requirement (a bonus after first purchase is allowed) since the spend budget will be gone.

Using the leftover spend:  There’s a good chance that some contestants will spend less than $15,000 towards minimum spend requirements.  In that case, they can virtually spend the rest on whichever of the 3 cards they chose in the draft.  None of that spend will be in bonus categories, though.  For example, if I had $3,000 spend leftover and I had chosen the Capital One Venture card, that would be a good choice for my final $3K spend since it earns 2X everywhere and I’d end up with 6,000 additional points.

Explore South America

Our challenges to-date have taken us to Europe, Africa, the Middle East, Asia, and Oceana.  A big hole both in our challenges is with points & miles travel to and around South America.

Interact with Each Other

The GUC trip was particularly fun because Nick and I travelled together.  Can the next challenge include more interaction?  For example, maybe we compete in teams (e.g. Nick and Stephen vs. Greg and Tim).  Or maybe we could do challenges that require competitors to meet up in various cities?  Or maybe we do something that includes some readers?

Reader Participation

We’ve often discussed the idea of including readers in the challenge in some way, but we’ve never figured out a practical way to make that happen.  If you have ideas for this, please let us know!

Comment Below

If you have ideas for the next challenge, please post your ideas to the comments section below!

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4 continents – 4 months

Take a 1-week trip each month to Europe, S. America, Asia, Africa. Around 1 week each. Using miles/hotel points.

Add in family or spouse (or mix of both) for each trip.

This adds practicality: typical trip length, more than 1 passenger, and typical USA vacation duration.

This will show many uses of miles and points all over the world. Maybe have some contestants in economy and some in business class.

Each “team/couple/family” has to use a different airline alliance. Again some go business and some go economy.

This is the basic idea. Details can be worked out based on number of teams, 2 versus 3+ travelers, etc.

This will also force usage/highlight of sweet spots to save in terms of miles required.


I don’t know exactly what the competition would be but I would love to see Team FM vs. Team Jet Lag (on YT). It’s a collaboration that would span written media and YT and I think would broaden the audience for both teams.


Picking a winner is impossible because each trip is so unique. You need to design a series of challenges that can be compared. Going to a world cup game. Going to an F1 race. Last min getaway with your significant other. Five nights in the Caribbean. Whatever it is, it needs to be comparable or eliminate the idea of a winner. Loved the draft, was probably my favorite part of the last challenge. Would love to see some unexpected thing, like, after the draft, each of the other players gets to name a challenge the other has to complete or a wheel or randomness that each person must spin. I feel like the award charts dictate your competition a lot, and that is fine I love a great find. But if I don’t take my wife to Italy soon, she is going to freeze my credit report and not tell me the password. Seeing how you would overcome some of these travel challenges that people who have a job and can’t just go on vacation on a random Tuesday would be interesting.

[…] Frequent Miler’s next challenge: What should it be? […]

d *

I mentioned this before can’t remember but maybe at an FTU… My suggestion would be to pick a destination and each person does it with a different focus in mind. So Greg could plan with high end resort type bookings, Nick could plan with family in mind and Steven could plan for best value for a longer stay with a pet. Maybe readers can choose the focal points? Maybe Carrie is also able to participate?

There might be overlap so for example, Nick might still go for the high end suite or all inclusive bc it works great for family, while Nick might also overlap with Steven’s choice of a place with a kitchen that works for a stay where eating out isn’t happening every meal/day.

And it would be interesting to see how people plan flights/methods of getting to destination bc maybe there are other ways besides flying?

What’s interesting about this challenge is everyone goes to the same destination and there’s the potential for collaboration/help each other create the best trip.

One could pick a popular destination like Las Vegas or Florida beach/amusement parks, or national park/scenic destination.

The other idea that came up in the podcast was a meetup. So if everyone was going to the same place and it was an easy one for folks to get to, then a meetup would be relatively easy.

So anyway, not a competition but definitely a challenge and I think it helps readers to see how to approach a trip given their focus/needs.

Last edited 2 months ago by d *

I think it would be great to involve readers as both the contest creators as well as the final judges.
Imagine if once a quarter you picked a reader at random and competed to design the best trip for them.
The criteria would be based on where that reader wants to go, the size of the party they intend on taking, and their own individual points and miles totals. You could all three then try and create the best trip for them and let them decide the winner.
Then, they could actually take the trip that was designed for them and document it themselves.
It might help individuals learn how to create itineraries with fixed amounts of points (you guys always seem to have infinite amounts). It would always be unique as some people would have specific ideas of where they want to go, others would not, some people might be going solo or as couples, others as a family, some would want to go in luxury, others in economy. The variables would always be changing.

Mark H

I would like to see no more secrecy. Maybe it takes away a strategy element, but I think it would be more fun and informative to read about and hear you discuss your plans as you make them.

Spencer Pederson

As many other commenters stated, I think the idea of involving readers is great. That said, I think it would be cool to have a competition focused on the readers being the competitors. (maybe this wouldn’t be a “pushing the points and miles boundaries” challenge but it could be a another type of challenge next year).

Basically, my thought is this:

  1. Greg, Nick, Stephen, Tim, and Carrie (or any mix of the FM team), position themselves in unique locations around the world (i.e. a certain resort, lounge, airport, landmark)
  2. The FM team gives out hints before the trip to help readers figure out where they will be “hiding.”
  3. Readers are tasked with finding each of the FM team members, with the first reader to find everyone (and maybe take a selfie?) being the winner.
  4. Or instead of just the first person finding everyone, there could be a weighting towards who spends the least amount of points/most luxurious travel.

Obviously, my idea is predicated on the fact that readers would be willing to participate. I think to get readers involved, some reasonable prizes would be required, but I know for myself it wouldn’t take much for me to be willing to do something like this.

The challenge would probably need to take place over the course of no more than 7-10 days (since not everyone has unlimited time off from work).

Anyway, this was basically just a brain dump of my initial thoughts, but I love the challenges the team does each year and I’ll keep thinking to see if any other ideas come up!


I would love to see a trip where you guys piece together an around the world itinerary using the 3 alliances. A minimum of 2 legs on each alliance with a preset total amount of points for booking the itinerary with a different hotel program for each stop (or a single one for all stops) being utilized


Closest to Antartica. It brings in South Africa, Australia/New Zealand and South America.


I like the idea of involving readers, not just in the selection process, but in the travel part. How about determining your trips and have a get together party with readers for a couple of days at each of the destinations. Points for the person that gets the most readers with bonus points for each 1,000 miles away from, say, Kansas City. So if 10 show up 6,000 miles away, 60 bonus points toward the prize. I bet a lot will try to join you.

Anthony Fantino

You should do a Amazing Race style competition with a certain destination as the goal such as Singapore or Antarctica, especially if you want to focus on points and miles for South America, Antarctica as your final destination would be pretty neat. There has to be certain parameters such as you can’t fly non stop to the destination obviously. Set a certain limit to the distance per flight. For example your first flight can only be a distance of 5,000 miles for a destination like Singapore or far less for Antarctica as the final destination more like 3,000 for the first flight, and shorter distances for the next flights and also limit the amount of miles redemptions per flight and limit of the total number of flights. This might mean some participants might have to resort to other transportation, train, bus, rickshaws! An Amazing race style competition to Antarctica going through South America should be your next challenge! You could even do the same fantasy style draft like your did in the last competition.

Anthony Fantino

Just watched the new podcast, a way to get the readers involved, you could choose where you are starting and ending and have the readers choose your next destinations along the way, provided that you are able to find bookable options.


How about 2 cards, one nation? Travel as many of the 50 states with 2 cards. Can use points for hotels/flights/car rentals. If you drive, then have to redeem the points for the gas spend. But there has to be a cap on driving, so you don’t end up driving the whole time.
With the nation under a recession, and budgets tight, more families are opting for domestic travel.


I think u got more posts on this then your trip.

Last edited 3 months ago by Cavedweller

Co-brand to Copacabana:

Two teams of two each draft 3-4 cards plus a small budget to build the best South American trip possible with co-branded cards only, no transferable points or cash back redemptions.


I’ll echo the many calls for booking awards for either 2 or 4 travelers instead of just 1. Another idea could be a trifecta battle where each contestant can “acquire” a common card duo or trifecta (Chase, Amex, Citi, Cap1, cash back..) and use a combination of SUBs and bonused spend exclusively within those ecosystems to plan a trip. And finally I’d love to see interesting uses of miles and points that are outside of the typical use cases of transportation and lodging, but still provide good cpp value. Cap1’s baseball tickets, Chase PYB for a silent disco beach yoga Airbnb experience, etc..

Ryan del Mundo

Props on all the challenges!

I’d love to see something more spontaneous / last-minute bookings.

I tend to travel without pre-set plans so I’m often at the mercy of last-minute flights.

Maybe you guys/gals all meet somewhere, then book something last minute (1-3 days out) to get where you’re going to the next spot (picked from a hat or user survey).

Then you guys can enjoy a few days in each city instead of running around like crazy as you seem to do on these challenges.

Since its all last-minute booking you could live-stream the booking process.

Pros: We could all learn a lot about last minute booking.

Cons: Might be stressful.

Intra-Africa award travel: Would love to learn more about this outside of using the excursionist perk
South America award travel: Hope you can make it down here, its wonderful! 12500 Alaska points Medellin-LIMA-Brazil. Will AK let me add in a stopover!? Stay tuned!


Involving your readers is a great idea! How about something where you each pick a prodigy/student/young grasshopper that you review their current haul of points and build/propose to them an AWESOME trip using only what they already have and readers vote on who helped their prodigy the most with scoring on Practical + Awesome + High Value. Or along those lines. MilesHQ mentioned something along these lines in their post below. Who is the “Master Sensei?”


Reader participation is paramount!
Readers choose an activity you all need to do on your trip, but you decide where and how. For example, you need to take a balloon ride, or need to do a day trek. Then we get to see where each of you goes to do this. We could have open submissions and then a poll to decide on the top 3 which you’d all do.

Also, readers could submit a brief summary of their favorite place that they’re willing to meet up with you and show you around. You guys choose (and coordinate feasibility with the reader) to make it happen. Reader gets themselves there and back (and shares how they did so with points and miles), but you pay for actitivies/food while there.
Alternatively – if the reader can’t join, they instead plan your activities for that destination (and perhaps join via Zoom or something at times). Bonus – Readers hold back 1 secret/fun activity they will have you do while there (like eat something unique or experience a local performance).



One month, point-to-point. Seoul to Buenos Aires, for example. Each player is given a hefty cash budget ($8,000) and 75,000 transferrable points. One person gets Amex, one person Chase, etc. Cash is important due to the many transit methods and experiences that can’t be booked by traditional points programs. 

Goal is to arrive at the end point having undertaken the most creative combination of methods of getting there. Think: passenger on a container ship, overnight sleeper bus, tuk-tuk, freight train, donkey…the more creative, the better.

All players must avoid touching North America. Players are encouraged to authentically experience the places/people they come in contact with, if possible.

Bonus: Any/all of the following factors can be added to spice it up:
–        In addition to North America, players must also avoid western Europe
–        Two players go one direction and two go in reverse (ex: Buenos Aires to Seoul)
–        If the desire is there: open it to a global circumnavigation
–        Each method of transit may only be used once

TMIMITW: The Most Interesting Man In The World


I like the idea of involving readers, and especially involving readers and their families. The real benefit of these challenges to readers is when you find a new way to use points and miles, especially when the “trick” or “sweet spot” applies to a trip we actually want to take. For me, the 7.5K Turkish sweet spot meant I got to take my family of 6 to Hawaii for the first time in our lives. However, the ANA RTW tactics are almost pointless to me as it wouldn’t be feasible for my family (with young ones) to take such a trip long enough to really make it worth it for many years. Other readers may find the ANA details invaluable, but not care about Turkish.

All that said, I think many readers have that one complicated dream destination that they’ve never been able to plan on points and miles. For me, it is a way to get my family down to Easter Island for 4-5 days to see the Moai and get to know the culture. We always watch the TV specials about Easter Island, read books, and talk about going (we even went to see the Moai in the Smithsonian), but have never made it. For others it might be the Galapagos, the Canary Islands, going to a historic building in some remote country, or whatever.

I suggest that you let readers submit an obscure dream destination, not Paris Tokyo, the Maldives, or a spot that travel blogs routinely write about and have one member of the FM team, who will not be competing, go through and pick the destinations that they believe to be the most interesting to plan that would also have wide appeal, but keep them secret from the rest of the team. Then have a live draft, but only allow the “competitors” (other members of the FM team) to know the destinations once you go live. Allow us to watch them research live on the air for 10-15 minutes and then have a random draw at that point (after they researched) for the order of selection. Then each competitor (based on the random draw) chooses a destination and plans a trip for the best points and miles value, bonus points for making it possible for the family that submitted the suggestion based on their particular family size and situation. For me that would be based on the fact that we are in Amex Popup prison. For others it could be restrictions due to only being able to travel on school holidays, not being able to get a Sapphire bonus because they just got one, having millions of miles from a certain airline due to years of business travel, or whatever.
Maybe the family does a write-up or posts photos of how the trip actually went. Maybe FM personalities act as travel companions and guide the families to the best airport lounges, help them rebook a flight if something goes awry, etc., along the way.


I would love to see something using “Stackery”.

You set a timeframe to accumulate and compound your offers, could be a month to a year.

You set a certain amount of reasonable “Spend” $1000-3000 or whatever, and keep an accounting of it.

For example; Current Amex Staples offer: I spend $100 at Staples to buy a gift card, and got $25 back.

The spend can be fluid (cash, credit card, gift card)

You count all of the travel portal cash back into your ledger balance.

The end result can be whatever you want, aka the best “trip”, “experience”, and we can vote on who made the most out of their “Stackery”


I do hope you can persuade Carrie to participate. She definitely brings a different perspective and, in terms of “total nights traveled” probably has more than three rest of the team put together!


Travel for 1 whole month straight using mostly points to book airfare and hotels

James R

Maybe make the booking portion be researched and booked in real time. I don’t know specifically how you do that – but give an each an hour to book the best award you can. This would also allow the readers to participate if they could find something in real time too. We could all search together and find something bookable RIGHT NOW.

I think a lot of the problem people have is finding award space. There feels like there is a “miracle” step in there. Most people can accumulate the points. But then a miracle happens – and some people are sitting in an around the world business cabin for 90k Amex points! And the rest of the people are sitting on 500k Amex points scratching their heads!


My idea is kind of a mashup of the ideas posted so far. The goal of the challenge is to show how the average person or family can travel on points with proper planning.

As of this post (from what I could find on Google), the average household income in the US is about $87.8k with the average household size being about 2.5 people, working out to about $35,120 per person. The FM team has a drawing to determine which household size they will represent with their equivalent household income. For example, Greg might draw a 1 person household with $35,120 income, Nick might get a 2 person household with $70,240 income, etc.

The challenge for the FM team would be to take the household income/size and for a one year time period, determine the best way to amass points for everybody in that household to have a great vacation paid for mostly with points. Each FM member would need to take into account not only what the best signup bonuses are, but what’s actually realistic to spend with their budget (assuming no MS is allowed). A 1 person household making 35k probably can’t meet a 15k in 3 months Amex Business Platinum signup bonus requirement but on the flip side, they’ll need less points to travel and finding award availability for only 1 person will be much easier.

To introduce some more spice to this challenge, instead of the FM team actually going on the trip, they could send FM readers along instead! The FM team would need to find a good way to go about this but my idea would be to have a google form where people of differing household sizes can put their hat in the ring and give some background on themselves and their family and why they want to go on the trip. This may be the hardest part of the challenge but it would truly make the challenge memorable.

This is just a rough idea and would need a lot fine-tuning but I think readers would really appreciate a challenge along these lines.

Another Jeff

Build the cost based on 2 people. Each contestant has to bring at least one family member.
Snake/random draft(randomized ahead of time)
Maybe do 1-2 rounds per week?
First round 1 flex card
Second round 2 airline cards
Third round 3 hotel cards
Fourth round category spend multiplier(s)
Might make sense to actually book flights before going to hotel round.

Each participant gets 2 steals(gift exchange style) and 2 “card application declined” to block others choices. If they don’t use at least 2 they get unsportsmanlike conduct and no category bonuses

You book your flights
Someone else books your hotels with their picks(maybe lead to cutthroat flight round followed by collusion/reconciliation in the hotel card round)
Someone else “upgrades” your trip with some set budget.(yay FM expense account, sorry Greg)
Flex card points spendable in any phase.

Loser of the competition gets to be Nick’s handler for Chicago seminars. He’s too popular 😉

Hopefully one of those ideas works out


I vote for a challenge for four business class tickets restricted to the same departure and return date during spring break or winter break.

The destination for the participants is fixed at the beginning via a lottery. For example, contestant 1 draws Delhi. Contestant 2 draws Bergen.

That’s a challenge.


Since 3 of you are going on these trips, why not draft an airline alliance for each member and see who can create the most innovative trip given access to a set of cards/points.

I see SkyTeam in Greg’s future LOL!!!


I concur with the comments about the next challenge being to book a dream trip for 4. While it’s fun to see how far you’ve been able to push things for a single individual, many of us don’t want to go it alone. We want our entire family to enjoy the experience. Bring your best stuff to the challenge and show us what’s possible!


First of all, I would be content with you doing a similar challenge to what you just did, but in 2 player mode with 6 cards (3 per player).

As an alternative, I tend to think that involving readers would be awesome.

You could have auditions of some kind from the readers where you vet their current experience and travel goals to find a good match for you to mentor. Each FM team member will choose a set number of readers as a “team” to “coach” on how to achieve their trip goal using, say 3 current card offers. I don’t think you should draft cards, just help them choose from what is available to best plan their dream trip and then make it happen. Your budgets from the recent challenge seem reasonable. Then have the readers vote on which coach and reader did the best job pulling off their trip.

Depending on how complicated you wanted to make it, you could focus on many things. You could each have a family of 4 trip, or a couples/honeymoon trip, or a solo trip, or others. If you wanted to really stay busy, you could do all three at once.

I think it would be really cool to see who coached the best family trip according to that family’s goals. Who coached the best couple’s trip? Who did the best solo trip?

Ultimately, you would have to define it quite a bit, but there so many ways this could be compared directly across FM coaches. If you wanted to be involved, you could even meet them at a stop along the way.

Of course it will be difficult to ensure that the readers will really play ball and earn the points and take the trips within a constrained timeframe, but I’m sure it can be done with proper vetting. Maybe it’s a multi-month challenge you can update us on with some frequency.


These all seem like great suggestions. I also think either a cobranded card or bank collection of cards challenge would be interesting. Each person would have to stick to one airline and one hotel chain, or one issuer (Chase, Citi, etc.)


How about visiting major land marks within the United States. Take a week or two. Also visit famous restaurants or even theme parks.


How to book airline partners in all three big airline alliances for a trip of four players? Choose the countries that are off the beaten path–which means only Asian, African and South American countries only. Also includes the sight seeing of the destinations that most bloggers do not cover because they all emphasize the journey over the destination– which I do not call “travel”. Travel is the destination. Journey is the means of transportation.

Jack S.

Love the ideas I’ve seen, thus far. My thought on the card draft is that you take $100k in annual household spend and parse it out into categories such as housing, groceries, utilities, dining out, etc., based on what you estimate is the typical FM reader’s spend. Then you draft 2-3 cards to try to maximize that spend. Whatever you end up with is what you book your trip with.

*Definitely Not Stephen's Partner* - Shae Pepper

Partners! You have to bring your partners, most of us aren’t in the points game so it brings in the newbie aspect and you have to only book using partner airlines, etc.

I second some sort of increased reader involvement.

I think a lot of the ideas here are great. Similar themes of more than one person to try and book for, different seasons for availability, etc.


Before planning for the next trip, please document the previous trip planning details, guide on other airline programs.

How do u plan for local sight seeing? What is the thought process for those.

Then for the next challenge, trip for 3 or 4 members.


hotel challenge – nicest stay for budget points or dream hotel destinations on points

T. Jones

There are a lot of interesting suggestions here, and quite frankly, a lot of good ideas.
Here are my thoughts after reading your article and each of the comments:
-It seems a lot of commenters really want to see an award trip for a family of four and not just one guy going around doing things on his own.
-You mentioned wanting to have more interaction with each other during these challenges. Why not plan a challenge that has the 4 of you traveling together?
-Explore South America. Yes. Do this. Explore each and every South American country (Venezuela excepted)
-You could include having a different team member arranging travel for each different county.
-You could also do some sort of Carmen Sandiego styled adventure where the other 3 need to figure out “Where in the world is Greg The Frequent Miler?”
-So how do you get readers involved in a practical manner? I dunno, but I will say this.
-When I visited Peru in 2018, a bout of foodborne illness made me miss my scheduled visit to Machu Picchu. I have the means to make a new visit, and would be happy to meet you guys there if you’d like a little reader involvement.
-Perhaps a different reader could meet the team in each different country?

Dr. McFrugal

I see a lot of the above comments and i am liking a lot of the suggestions, especially for traveling with 4 people and during the summer.

Here’s what I’d like to see. Get some reader participation/engagement and have readers submit destinations (could be Bucket list type of places or anywhere). Ideally there would be a lot of submissions, even domestically here in the US.

Then, there should be a reader poll to select two destinations in the United States. The would be a starting point location for all members of the FM team to travel together and start their journey. The second will be the ending point. In fact, there could be an informal or formal FM meet up with readers at these locations for even more fun and engagement.

Meanwhile, each of the members of FM are randomly assigned a number from 1-4. This is the order in which they pick “from a hat” one of the reader- submitted destinations. That FM member will be responsible for planning an amazing itinerary for all 4 members of the team to travel together to that particular destination. The randomly assigned number is also the order in which the legs of the trips will be taken (starting US location, leg 1, leg 2, leg 3, leg 4, ending US location). The duration of each leg should be should be at least 3 days but not more than 6. This can vary based on award availability and /or personal preference. The leg must obviously include atleast a one night stay at the reader submitted destination. Other stopovers and nights spent on the way to this reader submitted destination can be at the FM team member’s discretion (for example maybe Nick always wanted to visit Cartagena and it is a convenient stopover on the way to reader submitted destination of Patagonia).

The miles / cash budget and constraints could be similar to 3 cards and 3 continents. And there can be a card draft too. The card preferences of each person could vary a lot depending on the destination that is drawn.

Destination picking and card drafts can be done this winter for planned summer in travel. This would be relatable since many working people have to submit vacation requests at the end of the year for travel the following year. And summer is relatable to families with kids out of school, such as the last two weeks of June (like starting on June 19) and ending in July 4th. Something like that.

So for example, let’s say the readers select Miami and San Diego as US destinations to start and finish. And the randomly assigned order is: 1) Stephen (who draws Cape Town); 2) Tim (who draws Amalfi Coast); 3) Greg who draws Kilimanjaro; and 4) Nick (who draws Patagonia).

In this example, Miami is the chosen starting place. Readers can meet up there, hang out, party with the team in Miami before wishing them a bon voyage. Then Stephen is responsible for getting all four FM members from Miami to Capetown using the cards and remaining budget that he drafted. Tim then has to get everybody from Capetown to the Amalfi coast. Greg gets everybody from Amalfi to Kilimanjaro. Then Nick has to find a way to get everyone from Kilimanjaro to Patagonia.

But what about the final leg back to the USA you might ask. I’m this example, how do all four of them get from Patagonia to San Diego? Here’s where we can get reader feedback. Readers can submit itineraries and all four of FM members can decide which itinerary is best. That reader should get some sort of prize. Then we can all party in San Diego, conveniently where I live

Brian G.

My idea would be to have fixed time/date “checkpoints” in a few of the best lounges in the world (that have strict entry requirements) examples might be the QR Al Safwa First Class Lounge, LH First Class Terminal, etc. The checkpoint locations and times would be given to the contestants before readers so that they have the best chance of finding award flights that will give them access. Readers would be welcome to join, it would probably be a small group of readers that can join, making the interaction more meaningful.


Intriguing – like a crazy version of FM local meet-up, but in fancy lounges around the world with a prescheduled time window.


I had this typed up before reading – love this idea:
Each of you invites readers to join you for an unknown activity on a certain date in a certain city. Could be a food tour of a city, a day trip to a historic site, a boat trip in that location, etc.

Jan W

Love the idea of having a place (or two or three) where members could meet up! FM team could have activities for those who came–maybe visit a site and then eat together. Great way to let us meet each other! You would need registration but each person would fund their own expenses.


This is not really about the next challenge itself, but I’d like to see more documentation on how you each went about finding award space. Like, actual screenshots of the award calendar, third party tools, etc.. Maybe that is too basic, but for something like Nick’s Aeroplan trip, that requires a high level of planning, and would like to see how Nick actually put that all together.


Everyone starts with X number of Chase points and X dollars spend. Up to each contestant how to best utilize the points for combination of lodging (Hyatt, AirBnb PYB, airfare). Readers vote on preference (destination, luxury, use of points) etc


Okay: Carry Larry. Each contestant is given one million points to design the most luxurious possible trip from themselves and me, LarryInNYC. Bonus points awarded if they actually carry me from the Vienna Park Hyatt to the Cafe Sacher.

Dr. McFrugal

Mmmm…. Sachertorte


I don’t have all the details fleshed out, but I would like to see a competition where one competitor (or the audience/viewers) can sabotage the other competitor’s itinerary. They could force a flight to be ‘cancelled’ or they could force the competitor to the middle of nowhere. If that happens, the competitor would be forced to book a last minute trip, and they could score points on creativity (hot air balloon to your next destination? 10/10 in my book)


Around The World In 80K:. Each contestant has 80k points to travel around the world, starting on the same day and returning to the same point as they start from. The winner is the person who takes the longest to complete the trip, or the user who visits the most cities or sites mentioned in Jules Verne’s Around The World In Eighty Days.

If this can’t realistically be done in 80k points you could allow 80k airline miles and 80k hotel points.


Instead of just a single subjective “overall winner”, how about winners in each of a number of categories: Best airport lounge experience, best flight experience, best hotel experience, best excursion, etc. We could then have category winners and add up the points for an objective “overall winner”.


Make it more challenging like the 40k challenge. This last challenge was too easy, with too many points and unlimited on the ground cash. Put caps on cash, like many people do, and cap points.


I’d love to see a challenge where readers submit a “bucket list” destination trip and their available miles balances to accomplish it. Readers could vote on the top 3 picks they’d want to see be created and you three would randomly pick your assigned challenge out of a hat or something. The challenge would then be to come up with bookable itineraries to do the bucket trip using the original reader’s miles balance. Point of this challenge would be real life bookable trips with real life balances. Bonus points for not wiping out someone’s available points 🙂

Last edited 3 months ago by Dan

MY suggestion is no more challenges.


There are some great suggestions here. Love the idea of a ‘challenge hat’ from Grant as the point scoring aspect of the GUC challenge was very effective.

Having a new co-traveler such as Maise was a hit, which is something to explore further.

Love the idea of a relay race around the world, with all of you travelling together (and the dynamics that would introduce as you all travel so differently), meaning you have to find 3 awards (on the same flights or just to the same destination/ arrival time) for each segment of travel and each of you get to book a 1/3 of the trip.

Here are my suggestions for 2 player mode:

  1. You have to manage your and fellow traveler’s applications strategically, and book redemptions for both. Entertainment value is if the partner is a noob or just not yet into points. Special bonus points if the partner is a tolerating relative.
  2. Noob Master class. Each of you picks someone interested but new to the game (either from people you know or selected from reader applications – you get to define who qualifies). The candidate gets to define an overall goal (such as family travel (multiple seats), student travel (maximum destination travel, luxury not required), mature traveler (Luxury focused)). Needs to include how they are to meet the multiple minimum spend requirements. Timeline for points is 12 months to earn and 12 months to use. Can be an ongoing series, rather than a short event.
  3. Mileage blog competition! Each pick a fellow award blogger as a partner. Each picks 3 cards for the other (similar draft rules) from available offers. The contest is reader selected winners of “best of home team”, “Best of away team” and “Best of mixed doubles”, based on overall trip point value, overall trip / writing entertainment (FM blog + guest blog covering the trips). Teams can compete or collaborate against those 3 competing winner goals (or be sneaky and attempt to win multiple categories – somehow)
Last edited 3 months ago by rdover1

So I would like to see teams. Do the cc draft again. Each member would have to plan every other leg. Have a place that both teams has to meet up in and maybe do some type of reader interaction in that place. Or have readers plan the stop for the teams. Also you have to stay at least two nights in a specific number of stops. Maybe add in you have to spend time in Central or South America and/or Africa, but not Egypt.

A second thought is could you guys challenge another blog or points/miles podcast to do trips and readers judge.


Here is what I’d like to see (since this is something I am personally trying to achieve from my points and miles)

  1. Go through the card draft as you have done for 3C3C challenge. Or you can start with everyone having a fixed number of points of any currency or combination of currencies – this can be decided later.
  2. Find award availability (preferably business class seats) for 4 passengers on the same flight for a week-long trip (at least 5 days; at most 8 days)
  3. Book family friendly hotel(s) for the trip (so that means no more 1 king bed options!)
  4. Book rental car for the week – this will have to be an SUV or a near guaranteed option to upgrade to an SUV (through status, co-pay, etc.)
  5. Use whatever points you have been allocated to cover taxes, fees, resort fees, rental car cost, upgrade costs, etc.

My basic goal is to use the CC points to cover all trip costs that I’d otherwise not incur if I had stayed at home for vacation. So, I’d be willing to pay cash for any costs incurred on food, activities, gas, etc. since I’d incur those even if I spent that 1 week vacation at home.

This achieves two things –

  1. It makes the challenge relevant for most folks who read this (and other) blogs
  2. It will allow you to showcase or unearth some other sweet spots (e.g. using BA Avios to book expensive rental cars or Aeroplan Miles to book hotels)

You can make this more interesting (e.g. add P2 to help earn more CC sign-up bonuses and referral points) if you like the basic idea.


My idea is a 4-3-2-1 challenge.
4 is a flight from one airline in each alliance, that is randomly drawn in the draft (domestic airlines excluded, 4th alliance is non-alliance),
3 hotels, one from each chain (hilton, hyatt, marriott, hilton, wyndham, choice this would also be drawn,
2 fifth freedom flights,
1 weirdest flight (unheard of airline, unusual route, bucket list avGeek item (like Paro or Longyearben),
Budget would be unlimited, but the winner would meet each item, and have the lowest combo of points and cash.


Next challenge: RT Delta One to Italy in May for under 150,000 skypesos!


How about most value per points? I.e. try to fly on as expensive flights and stay as expensive hotels on the least amount of points possible. The person with the best trips and highest cents/point wins.


I’d love to see the challenges be more intermodal. What are some ways to combine interesting airline redemptions with overland travel by train, passenger ship, or something else entirely? I did a similar challenge for myself to only travel in a loop around Japan by ferry, for example, and that made me interact with my destinations and itinerary in a very new way.

Joe Y

A couple thoughts:

  • I like the idea of a “last-minute challenge,” as some have said. You can only book flights/hotels within the next couple weeks of a given date.
  • Pros vs. Joes competition: the FM team competes against a team of readers to see who comes up with the best trip. Would have to find some way to transfer points to the Joes, though, presuming most readers don’t have hundreds of thousands of points to burn on such a competition.

I liked the 3 cards 3 continents and especially no budget for the activities. I would suggest that at least one of the cards can be chosen regardless of whether someone else has already picked it. Everyone has to meet at the same spot for a meet up halfway through the trip and everyone has to have the same length of trip in days but can start and end at different places. I would also require at least 24 hours in each spot (or maybe 36-48?) and a minimum star rating of hotel per stop so it is more like a real vacation (I did not mind the creativity of Nick’s stops though). Maybe there is more cash ($1,500?) to help with the travel this time. Looking forward to it!


I think the challenge should start from the time you OPEN a new card and have to get the SUB and take a trip within 9 months of opening a new card. This will help many new people to the Points game and show it can be done. And no using P1 and P2. Should be solo trips using only one person’s cards.


Add restrictions for a minimum number of days at each location to highlight hotel sweet spots in addition to airline sweet spots. The 3 card challenge had way more stops than a typical traveler would take, as a result the hotels were an after thought.


Have any of you watched the British show ‘Race Across the World’? Teams of couples race to meet in different checkpoints around the world, ending in one particular location which serves as the finish line.

Something like that would be great, but points and miles-based. I haven’t really thought about it much more than that but hopefully someone else can flesh out the details.

Last edited 3 months ago by StephenH

The draft was cool, but in the end not practical, since we as cc customers aren’t constrained by what card another picks. It was also virtual, you didn’t actually apply for the cards. Having to deal with risk of rejection could make any contest more interesting. So I’d say a new contest could be simply $20k to far away. You got $20k to spend on MSR, AF, using benefits, etc. How can you use that to plan the most epic, luxe, bougie vacation? You have to actually apply and get approved, and can only use those card points and benefits for travel. No cash stays. No cash flights.

Obviously you’re all starting at different situations (over 5/24, have a P2, etc.), But that just can factor in to the degree of difficulty at the end.


Something about getting the highest cash value based on a given number of flight/hotel/card points — or the delta value between the cash rate of the flights/hotels/etc. and the estimated value of the points used to purchase. Eg. AA miles are worth 1.4 cents. If you pay 100,000 miles for a given flight, that’s worth $1400. What is the cash price of that flight? Subtract $1400 from that, and there’s your score. Add up the scores for each segment. One fun thing about this is the result is quantifiable and is measured in dollars. Cha-ching!

John II

I like the idea of quantifying a winner but I think the goal is to actually make it subjective. They want readers to be interested and feel like their votes count. Travel is so subjective anyways. Some prefer to stay 3 nights at an HGI in Wisconsin vs 1 night in WA Maldives.


Great point. Perhaps integrating the cash-minus-points value into a bigger contest?


The one thing I think these challenges have been missing is Family/Groups. Booking an awesome solo trip in business class with points/miles(or even for 2 people) is much easier than booking the same trip for 4 people.

So this challenge will involve 4 members of the Frequent Miler team traveling together. Each member will book a trip for 4 people and the entire team will go on each of the 4 trips. This has several advantages:

  • Gets the group interaction you mentioned
  • Everyone will have first-hand experience of the trip in determining who the winner is, instead of relying on the trip reports

I really enjoyed the draft format of the last challenge, so there are a few different ideas there:

  • Draft cards again, but with a higher limit(10?) and higher cash budget
  • Draft blocks of points instead of cards:
  • 750k Hilton Points
  • 350k Marriott Points
  • 200k Membership Rewards
  • 200k Ultimate Rewards
  • 250k AA miles
  • etc
  • Another element that could be part of the draft is the time window for the trip. Since everyone needs to go on each trip, it will need to be determined in advance who gets to book their trip for a particular month/2-week block/etc.
  • I’d also like to see a separate cash budget used for activities on the trip, so each trip is on a level playing field. This budget would be separate from the budget used for annual fees/taxes/etc

I think it would be hugely beneficial to the readers of this site and listeners of the podcast to learn from your experiences in booking these aspirational trips, but with the restriction that the trip is for a family or group of friends


I was thinking along the same lines (all the FM contestants travel together) but more as a relay: Greg is responsible for getting the group from the US to Europe, Nick from Europe to Africa, Steven from Africa to Asia, and Tim from Asia to the US. Each person has to plan the the flights and some number of nights of stays.

The budget could be the same for each leg, or different but preset (and agreed in advance) and the contestants would be randomly assigned to the legs. Or the legs could be assigned by reverse auction to the contestant that bids the lowest number of miles.


I don’t have a family so while this isn’t relevant to me personally, I must admit it’s a great idea for a challenge and a huge blind spot for blogs. I love Larry’s builds.


Love, love, love this relay idea. Would be so interesting to see what each team mate would come up with to impress the others.

I’d love to see a draft on who gets which leg (and start it in South America, both to make it harder and to work that continent in!). I imagine whoever has the last leg has a lot of pressure to impress the rest of the team!


I came here to recommend challenges for 3+ people. The challenges so far have highlighted what one person can do but aren’t very practical for families. This is a blind spot for points and miles blogs in general which are heavily skewed towards solo and couple travel, and I appreciate FM/Nick for writing about awards for parents with kids. It also seems like award inventory is going the wrong direction on this front with many outlets only releasing a single premium saver seat if anything. The challenge could also require/encourage innovation for booking suites and multiple rooms.

I also second the post’s suggestion for South America–another overlooked area by points and miles blogs that I’m guessing has some hidden sweet spots.

EDIT: I just responded to the first post I saw about families and didn’t realize it was the overwhelming consensus on here. Another suggestion: the traveler(s) have to travel to a destination with the requirement of staying there for 72-hours before moving on.


I love this idea, and the idea of booking for a family as many have said. If they don’t want to go on four different trips, they could always just plan one trip together. “Challenge” doesn’t mean that it has to be a competition against each other with a winner. It’s fine also to just be playing against the game (points style like GUC).

Big Chungus

Speaking as someone that has no kids and therefore no interest in all of the family ideas below lol:

You guys have already incorporated some themes of hobbies/interests into challenges and articles (Greg’s food theme for last challenge, Stephen seeing all of those troll things etc.)

I feel like there is room to do a really fun challenge where each participant (FM team or readers, either would work) designs a dream itinerary around a hobby they’re passionate about. Could be prix fixe dinners, a sport, something nature related.

For example, scuba diving would be my choice. In just the last year I’ve been able to dive in the Galapagos, Egypt, Komodo, Honduras and the Maldives thanks to points. Would be really cool to see someone pick something like hiking tall peaks, Michelin meals, soccer across continents etc.

It could even be a possibility to highlight ways to use points in non flight/hotel ways. Using C1 for MLB games, Skymiles for fine dining experiences, etc.


Make this challenge about impact: Show readers how miles and points can enrich and bring positive/long-lasting change to the human condition around the world.


I agree 100% and let them pay the Carbon Tax too to keep it Green..ALOHA


I like the idea of something with newbies: picking 3 (somewhat) random winners, then crafting credit card drafts, spending, and travel for them (like some travel/mileage services do when someone brings them their pile of miles, and their hopes and dreams!).


I would make the budget a little less restrictive. It is a balance between not wanting to get away from the core goal of nearly free travel but also not wanting to price yourself out of finding good redemptions. Sometimes a $300 fuel surcharge does make sense.

I also might make it somewhat more objective. Like a scavenger hunt or points if you achieve certain things, with some credit given for off the beaten path. Southern Africa or South America would be interesting.

Seeing you all have to do the same types of things with different currencies might also be interesting. Though it might lead to repetition.


How about team up with a newbie reader (you’ll have to define that) in some way because most of us don’t have quite the points and miles encyclopedia that you do and see what kind of trips they plan? Then “do better?” Or have a random selection of readers start with the same pool of currencies and design trips that we all vote on that you all eventually travel on? Then you can post mortem other opportunities they could have used.


Family of 4 travel on premium class (international business class or combination of business and first) would we great. I found booking hotel on points in Europe for 4 to be challenging. The last challenge would have been doable only as single (or couple in Greg’s case) but not on a family of 4, let alone with kids. So, something for families would be great.


National parks challenge? Potentially could be in different countries?

While the constant on the go thing is interesting to read about (and I’ve done on some solo trips) it’s not something most people would do.

Staying in more offbeat places. I know we churn for hotels and such but I know very few people who like to stay in them. They like airbnb, hipcamp, etc.


I was coming to say this! I think it’s so easy to find redemptions in larage urban areas, so making them go to National Parks (in any country) would be cool.


Seems like the next challenge should include what appears to be the hard to reach spots on points & miles: South America & SUB Saharan Africa {excluding South Africa}


I think a fun element would be planning a trip for each other. So, Greg could plan and organize a trip for Nick, and Nick wouldn’t know where he was going or what the plan was until it was revealed each day. Something like that.


I Ike this – or a version of this: Book the other person’s first flight only, then you plan/book the rest as you go. This would become a challenge about close-in awards, and your flexibility and creativity.

Paul LoBo

Around the world, but southern hemisphere only. Without taking flights that suck: Air India, South African Air.


I think if we’re going to do reader participation, how about have a reader poll to suggest the cards used for the next contest, as well as a poll for destinations?


How about adding some couch surfing with readers or reader meet-ups ?

Alexandra Hart

I’d say the next challenge should be seeing if you can try not to splatter pictures of yourselves over literally every single article…after a few years of reading it’s now reaching cringe territory.


agreed. Was busy traveling myself the past couple of months and I don’t read travel blogs/sites much per se when I am, but have been visiting less and less. Apparently, many here love the hero worship like angle, or living “vicariously” in some form, thus you got voted down so much. Maybe it’s just a societal thing.

What was that saying about pride and vanity again? Happens to the best of us…maybe FM team can recover and realize it has gone too far. And also learning to say more with less text/rambling. But if it results in more clicks, then I guess that works….but like you perhaps, I won’t be visiting much again.

Chuck from DoC

Love the team competition idea!

Christopher Gow

Something that can relate to more people. I am advanced in this game, but I know most of the people I know are not, and I am single with decent flexibility.

More relatable scenarios like planning for a honeymoon, family trip to Disney, family trip to Europe during summer break.

Could use the draft again, but add some other constraints: group of 2-4 must travel together at all times, can only use 5 days of PTO (so can leverage holiday weekends, but of course would be more difficult with availability), or maybe must include a holiday weekend.

Or family travel on the week between Christmas and NYE.


I agree with this idea….going to 10 places in 10 days doesn’t appeal to me. I want to see a 1 week vacation (for at least 2 people – if not 4) done with 3 cards and a normal budget.

Nick Reyes

Loving all the ideas here. Just wanted to quickly respond to the notion of like a “10 places in 10 days doesn’t appeal to me” aspect of this because I’ve seen similar feedback a couple of times and I think it misses the point of the contest to some extent. To be clear, the point of going to 10 places in 10 days isn’t to inspire you to want to do the same. It’s to show that (for example) whether you wanted to go to Egypt or Turkey or Oman or Thailand or Singapore or the Philippines or Dubai or Finland or some combination of a couple of those, you could make any of those trips possible with my three-card budget — pick any one or two that interests you and stretch it into a week if that’s your preference. I’ll add for the record that I have only one time in my entire life spent a full week at a single hotel, whether we’re talking before miles and points or after — that’s just never been appealing to me (though I certainly understand that I am in the minority on that!). I’m not saying that I’m not open to a trip to one destination — like I said, I’m loving the ideas here and I totally get that we all have different travel preferences and we obviously want to do things that appeal to many different people. I still do fully expect that no matter what we do most people will want to tailor it in some way to fit their personal preferences even if they want to do something similar.

Again, certainly not discouraging you from sharing what it is you want to see — please keep the ideas / preferences coming!


I like the nuclear family idea (“Are you telling me this sucker is nuclear?!” ~ Marty McFly), and being required to travel to one destination when the “kids” are out of school and the 9-5er/M-F working parents could get PTO.

I’d say there could be some flexibility on how many nights are spent in a single hotel for a week long trip. I think two hotels would be acceptable, since the average parent isn’t going to want to pack up the luggage every day to use the next free night cert at a different chain. Maybe a stretch to a third hotel for one night in a scenario of being near an airport on arrival or departure.

If the destination is a place where the public transportation isn’t realistic, then what tricks could be used to get a reasonable size rental for a good price?

Checked bags should be a requirement since, let’s face it, if you’re traveling with really young kids, you end up bringing half the house.


Just for Once but never again do 2 adults and 2 kids and see what they can do.That’s our job normally to scale the trips for whatever we need.But how many cards do they get 6 ??
I like it and they have the knowledge and time to do it too.

Last edited 3 months ago by Cavedweller

While not particularly interesting to me, personally, I think the honeymoon idea might get some traction. I think that a lot of people get into this hobby specifically for honeymoon planning and it’s an area where you can creatively build in some “wow” factor.


I agree with the idea of a “family” challenge, you’re missing a huge reader segment if you stick with guys bouncing around cities worldwide for 20 hour stints and sleeping on airplanes or in lounges. It may highlight the use of economy flights and non-luxury hotels……its not as sexy as business class and overwater bungalows but its realistic and damn challenging.

I’m on a family of four, low cost 12 night European cruise with award economy airfare and rooms on points thanks to your posts so it can be done….inspire us!


I’d love to see a challenge that involves booking awards for 2 people since most people would want to travel with a friend / family member / spouse.

I’d also like to see where there are 30-50 ideas / goals in a hat that you guys would alternate drawing from with different numbers of points. For example, visit 2 priority pass lounges in the same airport = 10 points. Cross the Atlantic Ocean = 10 points. Visit Santa’s Workshop = 25 points. Then it would be easy to keep track of everyone’s points to see how everyone did.

Nick Reyes

Quite a few people have mentioned a trip for two (including my wife, just for the record lol!). I realized in hindsight that I should have screen shotted my 3 Cards 3 Continents itinerary as I booked it — all but one of my flights (MNL-DOH) had space for at least 2 passengers when I booked (and the only one segment that didn’t, MNL-DOH, was a flight where I made a change and only the seat I cancelled and rebooked was available on that segment and I can’t recall whether there were two available when I originally booked that one. I generally find that availability for 2 (and sometimes more) is a lot easier to come by when you’re connecting other regions — it’s just the flights to/from the US where 2 or more passengers becomes more challenging (and even still I’ve now managed to get 4 passengers booked both transatlantic and transpacific on a handful of itineraries this year and next year). Anyway, the point behind my response was just to say that I should have realized that demonstrating the availability for multiple passengers should have been part of the story I told about my 3 Cards trip, it just didn’t occur to me that it would be important to a large segment of people (and silly me for not realizing that!).


I agree you guys are doing miraculous redemption, but only for one person. The challenge becomes more difficult when searching for multiple rewards. You should travel together at least two contestants.


My thought would be family and/or team competition. Family style redemptions and tactics would be awesome – finding 4 of anything for redemptions and reasonable accommodations on points for 4. That would be awesome to read about.


What about a “last minute booking” challenge? Give yourselves a 72 hour clock (or however long you want it to be!) and show what is possible when booking with points in such a short window before travel. Could dovetail nicely as a new version of the card draft, as well.


I’ve increasingly been booking last minute (I mean, like I’m in Europe now — Wednesday — returning on Friday or Saturday and haven’t booked it yet). I’m not sure other people consider that completely realistic, but I’d love to see a competition where the contestants could only book the first leg within three days of departure, and only book each subsequent leg when they arrived at their destination.


What about a domestic challenge? I think booking cost effective travel including rental cars effectively would be more challenging than long international business class.


If you want to maximize creativity in using points I’d recommend that you all start with X amount of the SAME transferable points. Also love the idea of working South America in there. Perhaps a challenge something like: you all receive 250,000 Amex points and some money, plan a one way trip starting in USA and ending in Santiago Chile. No restrictions on how the points are used (except maybe direct conversion to cash). A challenge like this would force creativity because you are starting with the same ingredients, but cooking up different trips. What you come up with would highlight how points can be used to make a dream trip for different travel styles.

The real one

How about a secret Santa type of trip? (ie, Nick has to plan/book Greg’s trip, Tim plans Stephen, etc., including major activities)?


Seven wonders of the world: Each contestant has to visit seven distinct sites that could be considered a “wonder of the world”. These could be entirely up to the contestant (and the choices they make would be part of the judging) or constrained in some way.

Planes, trains, and automobiles: Each contestant has to travel some set distance or number of countries using the maximum number of modes of transportation (plane, train, bus, car, boat, foot, animal, balloon, etc).

1001 nights: Contestants compete to see how long a trip they can eke out of a set budget of points and dollars.

Deep dive: Contests choose a single country or region and use points and miles to see it in the most depth possible.


I like this idea, also maybe include boats? Because to date, the great majority of the contest participation has stayed very close to international airports (with some notable exceptions with Stephen and Orkneys/Troll Hunting and also Greg with the train ride in S. Africa/Fjords).

Basically it would be nice to see some other areas further away from the big airports.

P.S. Greg hit it on the nose with the South America suggestion. I would suggest including the rest of Latin America. Have we seen much from Canada outside of Niagara falls?

Last edited 3 months ago by Aloha808
Nick Reyes

My wife vetoed the 1001-night trip where she’s left at home taking care of the kids for the next 3 years, just for the record.


Well, I didn’t actually think anyone would stretch it out that far. That would be as crazy as, I don’t know. . . going to the North Pole to meet Santa?


A business-class redemption from point A to point B (either one round-trip or two one-way redemptions) that have the most stopovers. Point limit if appropriate.

Jack Donners

I’d love to see a family challenge. For a lot of us the most significant restriction is that we need multiple awards since we don’t travel alone. Would love to see what creative ways exist to take 2-4 people on a trip