Party of 5! Frequent Miler’s 2023 team challenge


Last published June 1, 2023:  The latest Frequent Miler team challenge begins today!  This morning, we’ll make our way to the airport from the Hyatt Regency SFO and will fly Japan Airlines business class to Tokyo.  From there we will… well, you’ll see!  We’ll unveil our adventures as we go along.  As a reminder, team TYO (Stephen and Carrie) have planned the “starting in Tokyo” part of the trip; and team SFO (Nick and Tim) have planned the “starting in San Francisco” second part of the trip.  I’m the referee and will award points to each team based on the team making great use of points or free night certificates, getting great deals, finding great food, and planning amazing activities.  Since previous challenges focused more on flights, this challenge is focused more on lodging (for five).  As I wrote previously, I want to see each team uncover points & miles related opportunities that will benefit readers.  In particular, I plan to be very generous with awarding points to anyone who finds a great new way to use points for lodging.

The best way to keep up with the action for this challenge is to follow us on Instagram.  Need help with this?  See: How to follow and watch our Party of 5 Challenge stories on Instagram.

a close-up of a person's face
Look for a circle like this one at the top of your smartphone screen when you open Instagram. This means that we have published new “stories” for you to view. Click the circle to watch our latest exploits. Note: while viewing stories, you can press and hold the screen to pause; press the left side of the screen to go back; or press the right side of the screen to jump forward.

Personally, I’m excited!  Since my miles were used to book flights, I know where we’re going and each team is taking us to at least two destinations that are new to me, and I’m very much looking forward to all of them!  Beyond the destinations, I don’t know much about what we’ll do there, what we’ll eat, or where we’ll sleep.  Just in case, I packed a swimsuit, an underwater case for my phone, a jacket, and even hiking boots.  Will I need all that?  We’ll see!

Meanwhile, each team has made predictions about what the other team may do:

If each team’s predictions are any indication of their own plans, I’m confident both teams will do really well.  I have to say, though, that I was particularly impressed with team TYO’s predictions:

  • Hamilton in Puerto Rico
  • Park Hyatt Mendoza with Tim curating a wine experience (Tim was in the wine business for years before switching to the Frequent Miler whine business)
  • Punta Islita in Costa Rica (with built-in activities)
  • Machu Picchu
  • Patagonia!
  • A cruise through the Kenai Fjords

I love all of those ideas, so I’m hoping that some will come to fruition or that team SFO had even better ideas (is that possible?).  I’m also hoping, of course, that team TYO has made plans in Asia to rival their ideas for the Americas.  We’ll see soon!

The original post about this challenge follows…

Party of 5

Introducing Frequent Miler’s 2023 team challenge: Party of 5.  Each year, Frequent Miler team members compete to outdo each other in designing, 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.

Can we match those insanely high standards in this year’s challenge?  While previous challenges were mostly solo adventures, this year is all about booking travel for a party of five.

Challenge Background (Asia and the Americas)

Here we go again!  Late last year, the Frequent Miler team figured out dates for our 2023 team challenge.  We didn’t yet know what the challenge would entail, but we knew we needed to allocate time on everyone’s schedule.  We blocked two weeks in early June.  Then, in January of this year, first class awards on ANA were temporarily wide open.  We were able to book all five of us into ANA’s “The Suite” first class on a flight from Tokyo to San Francisco within the dates of our challenge.  I’m stressing that last point because it’s so remarkable.  Being able to book 5 first class ANA award seats in itself is an unheard of feat, but to do so within a preset block of dates is something I wouldn’t have believed possible.  But there you go, we did it.  Better yet, we were able to use what may be the best award deal that existed at the time: 55,000 Virgin Atlantic points per person for ANA first class!  Sadly, Virgin Atlantic has since raised the price to 72,500 miles per person.

So, we knew that part of our team challenge would involve flying from Tokyo to San Francisco.  Then, as we discussed ideas for the challenge that involved getting us to Japan, lightning struck again.  This time it was Japan Airlines that had wide open award space between San Francisco and Tokyo.  And once again, we amazingly found 5 award seats on a single flight!  This time it was for San Francisco to Tokyo and it was “only” for business class rather than first class, but it was still an amazing find.  I used 60,000 AA miles per person to book this flight.

At this point we now had a flight to Tokyo at the beginning of the challenge and then a flight returning from Tokyo in the middle of the challenge.  And so, we decided that this year’s challenge would have two parts: part 1 in Asia and part 2 in the Americas.

The Challenge

Two teams.  Two adventures.  5 travelers.  1 referee.  Team Tokyo will design a five day adventure in Asia, originating in Tokyo.  Team San Francisco will design a five day adventure in the Americas, originating in San Francisco.  The objective is to make great use of points and miles in order to build an epic 5-person trip.

What happened to the previous two-day per person plans?  In a previous Frequent Miler on the Air podcast and in an Ask Us Anything live event, we previously said that all 5 of us would compete against each other and each would orchestrate 2 days of the trip.  Since then, Tim came up with the idea of competing in teams, and we all liked that idea better than the original.  So, we jettisoned the original plans, but we kept the location assignments intact.  In the original plans, Stephen and Carrie were going to plan adventures in Asia, and Tim and Nick were going to plan adventures in the Americas. Those location assignments still hold, but now as teams.

The goal of this year’s challenge is to push the envelope on using points and miles to travel with a party of 5.  In a way, we’ve already done it by booking amazing international flights.  Assuming the flights go well, we’ve already won.  But there’s so much more yet to do!  Each team needs to plan travel, lodging, food, and adventures in Asia or in the Americas.

Real-time reveal: As we’ve done with past challenges, each team will keep travel details secret from each other, from me*, and from the audience until the travel actually happens.  As  the adventure unfolds, we’ll post frequently to Instagram (follow us there!) and regularly to this blog.

* In some cases I’ll know where we going in advance because I’ll be using my points or miles to book the flights or hotels.

Team Tokyo

Stephen and Carrie of Team Tokyo
Stephen and Carrie of Team Tokyo

Stephen and Carrie will work together to design, book, and orchestrate 5 days of travel in Asia, starting in Tokyo.

A heavy focus of this year’s challenge is about finding great lodging deals.  Given that Stephen has been living full time in hotels and Airbnbs and the like for over five years, he unquestionably has the most experience finding and booking lodging deals.  But most of this experience to-date has been in the United States.  Will Stephen’s ninja deal finding skills translate to Asia?

Carrie doesn’t have as much direct award booking experience as the others at Frequent Miler, but she has the most on-the-ground experience in Asia.  And while this will be Carrie’s first time actually travelling for a team competition, this ain’t her first rodeo.  She was the winner of our pandemic-inspired 2020 challenge StayCay to Far Away.

While Carrie and Stephen of Team Tokyo are looking very strong on their own, they have a secret weapon in their arsenal.  Carrie is married to Drew Macomber, author of Travel is Free.  While Drew has been out of the points & miles game for several years now, it’s worth pointing out that he’s a bit of a legend to us old timers in the game.  He didn’t publish often, but when he did his posts usually unveiled awesome new ways to push the envelope with points and miles.  In fact, he invented the crazy United Excursionist hack I used to earn the 40K to Far Away win.  I used his ideas to fly across the length of the African continent for only 10,000 points each way.  With the Party of Five challenge, Team Tokyo is allowed to lean on Drew’s expertise and creativity to plan their travel.  I don’t know if they will do so, nor do I know whether they’ll be able to tempt Drew back into this game for the purposes of this challenge, but as a fan of his work, I hope they do!

Team San Francisco

Nick and Tim of Team San Francisco
Nick and Tim of Team San Francisco

Nick and Tim will work together to design, book, and orchestrate 5 days of travel in the Americas, starting in San Francisco.

Nick has proven time and again that he’s a master at finding award deals.  In addition to stretching an Aeroplan award to its outer limits in his 3 Cards, 3 Continents win, he’s the guy that first figured out how to use Turkish miles to fly from anywhere in the United States to Hawaii for only 7,500 points one-way, and how to book an impossible LifeMiles award; and he found secret LifeMiles award pricing on select routes.  Nick alone will be hard to beat, but he’s not alone…

This will be Tim’s first team challenge.  I’m confident that he has very strong award booking skills, but how that will translate to the competition is anyone’s guess.  While Tim doesn’t live full time in hotels like Stephen does, he seems to stay in hotels often and he spits out a Bottom Line Review every 10 minutes or so.  My impression is that, like me (and unlike most others on the team), Tim prefers to use his points more for luxury than for savings.  I’ll be very interested to see if he’ll influence Team San Francisco towards that end.

The Referee

a cartoon of a referee

I won’t be competing this year, but I will travel as part of the Party of Five.  My primary role is to pay for everything.  Points and miles will come out of my personal stockpile.  All other charges will be paid for by the Frequent Miler business (which I solely own).  My secondary role is to referee the contest and award points.  I’ll award points to each team based on how good of a deal each part of the trip is, how great the experience was, etc. (more on scoring later in this post).

In a way, this challenge is designed a lot like the GUC Trip where Nick was tasked with building a great trip for the two of us using my Delta Global Upgrade Certificates (GUCs).  For that trip, I awarded bonus points to Nick for meeting various challenges and I gave him extra bonus points for exceeding expectations.  The biggest difference with this year’s challenge is that there will now be five of us travelling and two teams competing to earn the most points.

two men standing in front of a hot air balloon
Nick earned bonus points during the GUC trip by planning an awesome hot air balloon ride

During their planning, teams should keep in mind that I care about luxury, especially when it’s an awesome deal; I love going to new places and having new experiences; and I appreciate great food and I’m willing to try almost anything (see coconut worm, here).  But most of all, I want to see each team uncover points & miles related opportunities that will benefit readers.  In particular, I plan to be very generous with awarding points to anyone who finds a great new way to use points for lodging.

The game within the game

a person holding a video game controller

Update 5/25/23: Since this post was published, each team requested additional time for their plans and so we probably won’t have time for this “game within the game” after all.  I do think it would be fun though, so if we do find some free time during the trips, I may just spring some challenges on the contestants.

Original game within the game concept (no longer planned): Since Team San Francisco will have only four days to plan in the Americas, Team Tokyo will be given only four days in Asia.  But we’ll be in Asia for six days, so I volunteered to make plans for the other two days.  What neither team knew until now is that I’m planning to introduce a game within the game.  I’ll present mini challenges that have to be met in near real-time.  For an example of a mini-challenge (and this is just an example), maybe I’ll say “We need to be in Fukuoka by 10am tomorrow morning.  I already booked our way there, but it might not be the best way.  You have one hour to come up with a plan for how to get all 5 of us to Fukuoka on time.  I’ll judge the answers based on frugality and comfort.  Bonus points will be granted for coming up with a better plan than mine.  Extra bonus points if you convince me to cancel my plans and to go with yours.  Go!”  The idea in that example is that contestants might propose we fly, take a train, take a bus, rent a car, etc.  Whoever can get us to the goal in the least expensive but most comfortable way wins.  We’ll make sure to video record every part of this game within a game and maybe even do some of it over livestream.

Now back to the main challenge…


Lodging: When planning for hotels or other overnight accommodations, each team must adhere to these rules:

  • Sharing rooms is OK, sharing beds is not OK.  Everyone must have their own bed (or couch).
  • The couch rule: The planners get the worst beds.  For example, if the planning team books two rooms that each have two beds, one of the planners must sleep on the couch, or rollaway bed, or whatever.
  • Bathroom privacy is required.  Some hotels have parts of their bathrooms exposed to the bedroom without any way to enforce privacy.  For this challenge, the shower and toilet areas must be private, or we must book each person into their own rooms.

3 Square Meals: The planning team must ensure that everyone in the party gets to eat breakfast, lunch, and dinner every day.

No budget (but…): There is no built-in constraint to how many points or how much money each team can spend.  That said, a team will lose points if they spend more than I think is reasonable.  And I reserve the right to say no way to any part of a trip that is too expensive.  For example, if any contestant is thinking “I don’t mind losing if it means we can each spend four nights in our own overwater bungalow at the Four Seasons Maldives,” you better stop right there and come up with new plans.

Earning Points

I’ll award points to each team for lodging, travel, activities, and food.  Whichever team ends with the most points will be the winner.

Lodging Points

two beds in a room

Each team must make sure that all five of us have our own bed to sleep in each night.  Teams can earn bonus points for lodging as follows:

  • Sweet-spot bonus: Find or make use of a great lodging award sweet-spot.  More points will be awarded for originality and applicability.  For example, a team will win a jackpot of points if they uncover a new way to get great value using points to book award stays and if that new way has broad applicability.  For example, if a team finds a way to get great value using points to book Airbnb stays, that would earn a jackpot of points because it would be both new and broadly applicable for all kinds of future travels.  Finding a great way to use Hilton points for a specific Hilton property is an example of finding a new sweet-spot that isn’t broadly applicable.  That would earn points, but not nearly as many points as a find that is more broadly applicable.  Making use of an already known sweet-spot lodging award will also earn points but not as many as with a new finding.
  • Bonus for using Greg’s certs & credits: I have a number of lodging related credits and free night certificates that I’d like to use during the challenge: Marriott free nights certificates (both 35K and 50K); Hyatt category 1-4 certificates; IHG 40K certificates which can’t be topped off; $200 Amex Platinum Fine Hotels & Resorts credits; and a $50 Sapphire Preferred hotel credit (must be booked through the Chase portal).  I’ll award bonus points for making good use of these certificates.  For free night certificates, “good use” means that the hotel otherwise would have cost a lot of money and that the point-cost would have been close to the full value of the certificate’s top value.  For the Fine Hotels & Resorts credits, I’ll award extra points for booking a hotel that cost around $200.  Similarly, with the Sapphire Preferred $50 credit, I’ll award bonus points for booking a room that costs just over $50.
  • Privacy bonus: The less we have to share bedrooms or bathrooms, the more bonus points will be awarded.
  • Comfort bonus: More points for more comfort.
  • Luxury bonus: More points for more luxury (but I still need to judge it to be a good deal).
  • Frugality bonus: More points for spending fewer of Greg’s points (or for spending less of his money).
  • Novelty bonus: I’ll award bonus points for booking us into unique accommodations. For example, I might award bonus points if we stay in a treehouse, an igloo, a cave, a ‎Ryokan, etc.

Transportation Points

two men sitting in a plane eating snacks
Greg and Nick flew Spirit’s “Big Front Seat”.  This was an example of an economical and comfortable form of travel.

Each team is responsible for planning all transportation within their four days.  This could include long distance transportation (via planes, trains, or boats for example) if the team decides to take us far, and will definitely include local transportation to move between airports, hotels, and activities.

Teams can earn bonus points for transportation as follows:

  • Sweet-spot bonus: Find or make use of a great transportation award sweet-spot.  More points will be awarded for originality and applicability.  A team will win a jackpot of points if they uncover a new way to get great value booking award flights and if that new way has broad applicability.  For example, if a team finds that it’s possible to get great value using Iberia Avios to book Emirates flights, that would be an awesome find that is both original and broadly applicable for future travel.  If a team finds, for example, that they can get great value using Singapore miles to book a single specific route, that would be original but not broadly applicable.  Both would earn points, but the first would earn more.  Making use of an already known sweet-spot award will also earn points but not as many as with a new finding.
  • Bonus for using Greg’s extra miles: When using my own miles to book our flights, I’d prefer to use miles I already have rather than transferring from a transferrable points program.  To encourage this, I’ll give bonus points for making good use of my existing miles.  This includes: AA, Alaska, Avianca, Cathay Pacific, Delta, and United.  Extra bonus points will be given for finding good uses for my miles that are set to expire with no easy way to renew them: ANA and Singapore Airlines.
  • Comfort bonus: More points for more comfort.
  • Luxury bonus: More points for more luxury (but I still need to judge it to be a good deal).
  • Frugality bonus: More points for spending fewer of Greg’s points (or for spending less of his money).
  • Novelty bonus: I’ll award bonus points for booking us on unique modes of transport.  If animals are involved they have to be treated well.

Food Points

a man and woman in life jackets eating food
Greg and Maisie enjoying barbeque pork skewers and rice porridge at the Mekong Delta floating market.

Points will be awarded for feeding the team with new foods, great food, and economically:

  • Novelty Bonus: Bonus points for each food item that we eat that is new to at least 3 people in the group.  Double if it is new to all 5 of us.
  • Yum Bonus: Bonus points for delicious food.  We’ll know it when we eat it.
  • Deal Bonus: Bonus points for food that is a great deal.

Activity Points

Segway tour of Washington D.C. for less than $22 Don't mind if I do
Stephen enjoying his Segway tour of Washington D.C. during the 40K to Far Away Challenge

Each team must plan fun and interesting activities for the group!

  • Novelty Bonus: Bonus points for each activity that is new to at least 3 people in the group.  Snorkeling in Bay of XYZ doesn’t count as being new just because we haven’t snorkeled in that particular place, but snorkeling with manta rays (for example) would count.
  • “Wow” Bonus: Bonus points for activities that wow us.  We could be wowed by activities that are exciting, interesting, beautiful, whatever.  We’ll know it when we experience it.
  • Deal Bonus: Bonus points for activities that are a great deal.

Two for One Bonuses

Bonuses will be awarded when multiple goals are achieved with a single booking.  These deserve bonus points because they’ll save points and money.  Here are some examples:

  • All-inclusive cruise: A cruise might take care of food, activities, transport, and lodging all at once.
  • Hotel extras: A hotel booking is likely to include some food (such as breakfast), but may also include some activities, local transport, etc.
  • Transportation “lodging”: An overnight flight, train, or boat ride might act as our lodging for the night.
  • Transportation related dining:  When travelling we might get fed on a train or airplane, or in an airport lounge.

Audience Input

While we haven’t worked out the details yet, we plan to provide a way for those following along at home to lobby for more (or fewer) points to be awarded. The decision about which team won won’t happen until after the lobbying is done.  I hope and expect that audience input will have a large impact on the final results.

For example, maybe you’ll see that I gave Team Tokyo 5,000 points for booking a night in the Taj Mahal for 20,000 Hilton points per bedroom.  You didn’t realize that 5,000 points was too little until you later see me award Team San Francisco 5,000 points for booking us into a Holiday Inn off the highway.  So, then, you will have a way to argue that the Taj Mahal stay deserved far more points because 1) it was a remarkable feat because people don’t really get to stay overnight there (except on April first); 2) somehow Team Tokyo used Hilton points to do it; and 3) 20,000 Hilton points per night is a bargain at a Hampton Inn, let alone at one of the wonders of the world.

Thoughts / Suggestions?

Are you looking forward to the challenge?  Do you have any suggestions for how we can tweak things to make the challenge more fun or interesting?  Please comment below!

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

oldest most voted
Inline Feedbacks
View all comments

[…] and I have different numbers for 2023 because I went abroad without her for the Frequent Miler Party of 5 challenge. Shae went to three countries, while I went to […]

[…] My time with that company was cut short and to be honest, I was alone (Stephen was on the Party of 5 trip) and I was devastated. But, with some therapy, excellent friends, my awesome and supportive […]

[…] Not sure what this challenge is? Start at the beginning for a full explanation. […]

[…] had mentioned in his post explaining the Party of 5 challenge that he’d give bonus points for using certain hotel booking options such as certain hotel free […]

Challenge accepted

I love these challenges. We can learn so much from them and they are fun to follow. Have fun!


I love the fact that you’re emphasizing lodging when awarding points, as that is the most difficult part of organizing a family trip using points.

Charlie Moose

Except Greg’s Million Points/Miles in a Month Challenge……I do not like this other Challenges, I would rather just have your normal wonderful daily content. Please no sleeping on park benches to save money again. Just say no to Challenges, IMHO.

Charlie Moose

these not this


Are you this much fun at other parties, too?

Charlie Moose

Sorry Larry for having an opinion that you do not like. Let he who is without sin throw the first stone.

Jesus, Bronx NYC

Hey Charlie I agree with you about rather having the normal daily FM content.

Last edited 11 months ago by Greg The Frequent Miler
Charlie Lion

I strongly disagree with this opinion and hope that it’s not taken into account in the editorial process. It’s just awful that you would want to get rid of good content.


Last travel challenge, Nick went to see Santa in the north pole. I don’t know how anyone is going to top something like that.


So…when does it start??? I’m going to Japan in late June and would LOVE to be armed with some of your amazing ideas!

[…] will also be traveling at that time with Frequent Miler on this year’s challenge trip, Party of Five. Truffles will be having her own vacation from our travels at a Rover (our referral link) in […]


Definitely award more for using orphaned points from transferrable programs. X2 if they expire at all. X3 if they expire within 12 months. X4 if they expire within 6 months. X1 in addition to the above if they’re Lifemiles since you had to speak to them on the phone to orphan the points.


Guys, I can’t wait for this year’s challenge! I have finally amassed enough points for my epic vacay and it will be in Asia so I’m gonna be particularly attentive to the Asia portion of the challenge. Good luck to both teams. And, as usual, I’m wishing I lived Greg’s life for just minute. :-/


I don’t know who drew these cartoons, but they depict each person so well – nicely done!


My guess is Caroline, btw. (I don’t know how to edit the comments.)


Can’t wait! Sounds like a lot of fun!

Evan F

You all are the best! What a fun challenge and way for us to see all your ninja skills in real-time action. Looking forward to the updates, posts and especially the pictures!!!