And the Party of 5 winner is… (Final Answer)


Wow, what a trip!  Or, should I say “two” trips?  Over a two week span, the Frequent Miler team travelled through Asia and southern South America.  And we had an incredible time.  On Monday, Stephen published an overview and accounting of the trip organized by Team Tokyo (Philippines, Macau, and Tokyo).  And on Tuesday, Tim published the same for Team SFO (San Francisco, Santiago Chile, Buenos Aires, and Iguazu Falls).  And now for the hard part… I’ve decided which team won the Party of 5 Challenge…

In the original publication of this post on Wednesday June 21 2023, I declared that the challenge was a tie, but I invited readers to convince me I was wrong.  Jump to the section titled “Who won? Final Answer” to see the final results.

The Party of 5 Team. Clockwise from top-left: Greg, Tim, Nick, Carrie, Stephen

The Party of 5 Team. Clockwise from top-left: Greg, Tim, Nick, Carrie, Stephen.  This was our attempt to arrange ourselves like in the drawing on the hat.  This photo (actually a still clip from a video) was taken in San Francisco on the day that the whole challenge began.  Over the next two weeks, those smiles and laughs continued nearly nonstop.

Here’s the Party of 5 arrangement we tried to mimic.


Each year the Frequent Miler team does a challenge to see who can stretch the value of points and miles the farthest.  In the past, we’ve competed against each other on our own individual trips.  This year, we shook things up by traveling together as a party of 5.  Team Tokyo (Stephen and Carrie) were tasked with building an awesome trip that began and ended in Tokyo, while Team SFO (Nick and Tim) were tasked with building a trip that began in San Francisco.  My task was to award points to each team based on how well they accomplished the many goals I laid out in this post: Party of 5! Frequent Miler’s 2023 team challenge.

If things had gone to plan, we would already know who won.  For the first 4 days or so, I awarded points every day to Team Tokyo based on where we stayed, how we traveled, what we ate, and what we did.  Then, I fell behind.  We were simply too busy or I was too tired to keep it up.  But, I did continue to record notes every day.  Then, my backpack was stolen, along with all of my notes.  That was it.  I gave up on awarding points along the way.  This post, then, is a reset.  Rather than awarding points for every little thing as I had been doing before, I’ll award points in big buckets.


Airbnb Le Manoir des Bougainvilliers - Just a taste of the decor
Team Tokyo’s Airbnb

One of the hardest things about traveling with a party of 5 is finding a way to house everyone comfortably and economically.  Using hotel points can be problematic since many hotel rooms are limited to 2 or 3 people and so it can cost double or triple the points to put up 5 people in a hotel.  We know that using Wyndham points to book Vacasa Vacation Rentals is a great way around this issue, but Vacasa doesn’t have much going on outside of the U.S.  I had hoped that this challenge would lead us to find more opportunities like Wyndham-Vacasa: where we could use hotel points at reasonable rates to book homes or multi-bedroom apartments.  Unfortunately, neither team uncovered anything new in that area.  But we did stay in some fantastic lodgings…

Both teams booked two nights of luxury by booking us into two or three rooms at a time.  Team Tokyo booked two rooms at the Four Seasons Macau and three rooms at the Grand Hyatt Macau.  Team SFO booked two rooms at the Ritz-Carlton Santiago and two rooms at the Park Tower Buenos Aires.  Outside of those luxury nights, team Tokyo booked us into a fantastic Airbnb for two nights, a nice Holiday Inn Express for one night, and a very nice Hyatt Regency for another night.  Meanwhile, for the non-luxury nights, team SFO put us in a not-so-nice Holiday Inn for one night and a spooky Wyndham hotel for another.  We also had an overnight flight on LATAM business class.  Team SFO also succeeded in using expiring free nights and credits to good value.  This included IHG 40K non-top-offable certs, a Marriott 50K cert expiring within a week, and a $50 Sapphire Preferred credit.

Lodging Scores

  • Team Tokyo: 40,000
    For providing a great deal of privacy and comfort throughout the trip, and for putting us up for two nights in the crazy-amazing Airbnb in the Philippines.
  • Team SFO: 15,000
    For making great use of expiring credits and certificates.  Additionally, the LATAM flight provided reasonably comfortable overnight lodging one night.


LATAM Business Class
LATAM Business Class

Finding award flights for 5 can be really challenging, but both teams managed it.  Team Tokyo put us in business class for 2 out of 3 short flights, and Team SFO put us all in business class for their one very long flight (Los Angeles to Santiago) and in economy for several short flights.  For the Team Tokyo business class flights, I personally would have opted to save miles and money by booking economy since these were short flights, but as it happened I very much appreciated the more comfortable naps I was able to manage in business class.

Flight scores

  • Team Tokyo: 15,000
    For finding award space for 5 on all flights, and for finding reasonably priced business class awards on two out of three flights.
  • Team SFO: 30,000
    For uncovering a great sweet-spot award: Use Alaska miles to fly LATAM business class from North America to South America, plus add a free stop-over, for only 45,000 points per person.


Private dinner experience in Buenos Aires

One of the key rules of the challenge was to provide three square meals per day.  Team Tokyo was spot-on with this one (the only time we didn’t have lunch, it was available, but we were too full from breakfast to eat it).  That said, other than when Tim and I went out on our own in Tokyo to get a sushi lunch, Team Tokyo never took us outside of our hotels or Airbnb to sample local foods (yes we ate local foods within the hotels and Airbnb, but that’s not the same).  Meanwhile, Team SFO made sure that we experienced local cuisine at every stop and even included a home made four-course dinner with wine in Argentina.  They just rarely provided lunch.

Food scores

  • Team Tokyo: 20,000
    For providing three solid meals per day and often very frugally (by relying on hotel breakfasts, for example).  10,000 of these points were due to finding the Airbnb which provided a private chef for breakfast and dinner!
  • Team SFO: 25,000
    For ensuring that we always ate locally outside of hotels or airports at every stop.  I would have awarded 30,000 points, but detracted 5K for going hungry at lunch time.

Yucky Food Competition Bonus

At the Hyatt Regency Tokyo Bay, Carrie of Team Tokyo and Nick of Team SFO faced off.  The omelet station weirdly offered marshmallows as an optional omelet ingredient, and since Nick hates both eggs and marshmallows we had to find a way to make him eat a marshmallow omelet.  It was imperative.  The opportunity came when Carrie discovered that the okra on her plate was covered with something slimy and gross looking.  She simply couldn’t eat it.  That is, she couldn’t eat it until there was a points-opportunity knocking.  I promised 10,000 points to whoever could eat and finish their yucky food first.  Carrie won!

  • Team Tokyo yucky food bonus: 10,000
    For Carrie finishing the okra before Nick finished his omelet
  • Team SFO yucky food bonus: 0


Flower exhibit for Party of 5 TeamLabs
teamLab Planets TOKYO. This may have been the single most fun activity across both trips.
Mural Lessons in Buenos Aires with local street artist “Luxor”.  We all loved this experience!

Both teams did a great job in organizing activities.  Team Tokyo lead us to what may have been the single most fun activity, teamLab Planets TOKYO, which was like an amazing playground for adults.  On the other hand, Team SFO was most successful in making dreams come true with Mural Lessons in Buenos Aires with local street artist “Luxor.” (read about it here).  And when things went wrong, I thought that Team SFO was more successful in saving what was left of the day.  Plus, Team SFO piled on an incredible assortment of activities over a short amount of time: a coastal walk in San Francisco, go-cart racing in Santiago, a gourmet dining experience in Buenos Aires, the street art experience also in Buenos Aires, and multiple exciting ways to see the Iguazu Falls (helicopter, boat, walk).

Activity scores

  • Team Tokyo: 25,000
    For organizing the excellent snorkeling adventure, and my favorite of all activities: teamLab Planets TOKYO
  • Team SFO: 40,000
    For organizing amazing activities at every stop, and most of all, for literally making Carrie’s dreams come true with the street-art experience (which was fun for all of us, by the way!)

Travel Big Picture

We did heart Puerto Galera
Feeling safe with “mom and dad”

There are important aspects to travel that aren’t covered well in the categories presented above.  Both trips were fantastic, but they felt different.  With Team Tokyo’s trip, I felt taken care of as a passenger.  Even though we had some SNAFUs in Macau, I generally felt like Team Tokyo had thought through all of the logistics in advance, they scheduled plenty of time to get from one place to another, and they ensured that we had adequate time each day to work and/or rest.  With Team SFO, though, we had non-stop fun, but that part of the trip often felt chaotic and stressful.  We often rushed from one place to another for fear of missing a flight or a scheduled activity.  We often crushed 4 of the 5 of us into the backseat of small Uber cars because we couldn’t get any Uber XLs to come (or when they did, they were small too).  And we rarely had time to work or rest.

Travel big-picture scores

  • Team Tokyo: 15,000
    For making the kids feel safe during travels.

Budget Big Picture

Team Tokyo total spend:

  • 374,500 points
    • 262,500 AAdvantage miles
    • 55,000 Avios
    • 57,000 Hyatt points
  • $3,688

Team SFO total spend:

  • 279,545 points
    • 225,000 Alaska miles
    • 25,000 Bilt points
    • 22,795 Rapid Rewards points
    • 6,750 Wyndham points
  • $2,962

Team SFO spent fewer points and fewer dollars than Team Tokyo and yet they took us to more activities, including some that you’d normally expect would be very expensive (such as the helicopter ride over Iguazu Falls).  On the other hand, Team SFO wasn’t required to get us back home whereas Team Tokyo had to get us back to Tokyo.  If Team SFO had been required to get us back to the U.S. and had used the same 45K per person Alaska award as was used to fly LATAM to South America, they would have spent far more miles than Team Tokyo.

Given that I can’t really do an apples-to-apples comparison of the two trips budget-wise, I’m left instead pointing out some of the budget pluses and minuses:

  • Team Tokyo’s Airbnb was a great deal for about $210 per day.  Plus, I got a $50 gift card from the deal and earned some British Airways Avios.
  • Team Tokyo could have saved points or cash at a couple of hotels by booking us into two rooms instead of three.  Previously, under lodging, I gave them points for comfort and privacy, but need to detract points here for the budget.
  • Similarly, Team Tokyo could have saved points and/or cash by booking short economy flights instead of business class.
  • Team SFO wins the budget category by often choosing the cheaper path over comfort.  All flights but one were in economy and we stayed in a couple of low end budget hotels.

Budget big-picture scores

  • Team Tokyo: 5,000
  • Team SFO: 20,000

Score totals

  • Team Tokyo Total: 130K
    • Lodging: 40K
    • Flights: 15K
    • Food: 20K
    • Food Contest: 10K
    • Activities: 25K
    • Travel Big Picture: 15K
    • Budget: 5K
  • Team SFO Total: 130K
    • Lodging: 15K
    • Flights: 30K
    • Food: 25K
    • Food Contest: 0
    • Activities: 40K
    • Travel Big Picture: 0
    • Budget: 20K

Based on my scoring, the competition ended in a tie!  I think that’s appropriate because both teams engineered incredible trips, but each with offsetting pros and cons.

Who won? Final Answer

On Wednesday, when I first published this article, my tentative answer was that the two teams tied, but I invited readers to convince me one way or the other.  And over the past two days, convincing arguments surfaced… for both sides.  Commenters argued passionately in favor of Team Tokyo.  Others argued fervently in favor of Team SFO.  That didn’t settle anything for me!  So, I went back to my original Party of 5 post to compare the rules as laid out then vs. the trips we experienced…

In the original post, I asserted that lodging was key.  Here are two relevant quotes:

A heavy focus of this year’s challenge is about finding great lodging deals.


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.

Team Tokyo took my words to heart and based most of their plans around lodging for a party of 5.  They found an amazing Airbnb property in the Philippines and built a trip around that.  No, they didn’t find a great new way to use points for lodging, but the Airbnb was incredible.  Additionally, all of the rest of the lodgings on the Team Tokyo trip were comfortable and most qualified as luxurious.  Team SFO, meanwhile, put us up in a couple of anti-luxurious hotels in addition to two luxury hotels.  So, based on lodging being the primary focus of the challenge, I should give the win to Team Tokyo, but…

In the same post, I detailed ways to earn bonus points for lodging, transportation, food, and activities.  I offered bonuses for making good use of my existing points and free night certificates, especially those that are soon expiring.  I also offered frugality bonuses and novelty bonuses.  On each of these factors, Team SFO deserved more points.  They used more of my expiring certs and found more frugal lodging options overall.  They also took us to more places and activities that were novel to 3 or more of us (which was the threshold to get novelty bonus points).  So, based on my promises of how I’d award points, I should give the win to Team SFO.

Do you see my dilemma here?  Both teams should win.  And that’s the final answer…  Both teams won the 2023 Party of 5 Challenge.  Is it a cop out?  Sure, but I believe it’s also the right answer and that’s lucky for me because after spending two weeks with this wonderful group, I really don’t want to let down any one of them.

teamLab Planets Tokyo. Clockwise from top-left: Tim, Carrie, Greg, Stephen, Nick.  Can I really let anyone in this group down?  No!

Rather than picking a single overall winner, I’ll hand out some mini-awards…

Best logistics: Team Tokyo

In the jeepney on the way to our Airbnb
In the jeepney on the way to our Airbnb

With an exception or two in Macau, Team Tokyo did a great job of making sure we had good local transportation at every stop.  I loved that they were prepared with a van to take us from Manilla to the ferry-port to go to to Puerto Galera, and then had a Jeepney waiting to take us to our Airbnb; and the same in reverse when we left.  Additionally, for each flight we arrived at the airport with plenty of time to spare.  And, we ate well and often.  I tend to get in a mood when I get overly hungry.  To paraphrase Bill Bixby in The Incredible Hulk, “you wouldn’t like me when I’m hungry.”  Team Tokyo never let that happen.

Best local experiences: Team SFO

Santiago walking tour

At every Team SFO stop, we had local experiences.  This included a walk, a restaurant, and a bar in San Francisco; a restaurant, a bar, and a walking tour in Santiago; and a private dinner and a street art experience in Buenos Aires.  Even though it was a whirlwind trip from one place to another, I felt like Team SFO did a great job in making sure that we really experienced a bit of what makes each location unique.

Best lodging: Team Tokyo

Our 8 bedroom Airbnb in the Philippines was absolutely amazing, and for modest extra fees it included a private chef and local transportation by Jeepney!  You can read all about it here.

Le Manoir des Bougainvilliers

Reader’s choice award: Team SFO

Nick and Tim of Team San Francisco

On Wednesday afternoon, Carrie posted trip videos for those who missed them on Instagram and she included a “who won?” poll.  The results were decisive for Team SFO:

Who should win the 2023 Party of 5 Challenge?

  • Team San Francisco (Tim and Nick) (52%, 126 Votes)
  • Team Tokyo (Stephen and Carrie) (33%, 80 Votes)
  • Keep it a tie! (16%, 38 Votes)

Total Voters: 244

Loading ... Loading ...

Best tie award goes to…

The Frequent Miler Insiders Group agreed that a tie is best with 42% picking that option.

And on the blog…

  • Paul: “Tie seems fair. There were some great ideas from both teams.”
  • MickiSue: “I don’t know how your teams feel about it, but I’m fine with it being a tie. The goal of a vacation is to take home home fabulous memories and experience amazing things. At least, to me it is.  It appears that both teams did just that, and both very well. A tie, it is!”
  •  sjs: “I have to agree with the tie. Both teams did an amazing job with the constraints given and the obstacles faced. I loved following along and checked IG constantly for updates!”
  • Rachel: “I’m for leaving it a tie! I see amazing innovation and finds in each group. Nothing stands out as “better than the other by a long shot”…”
  • JeffP: “Leave it a tie…”
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Greg is getting soft in his old age! With that said, congrats to all! Looked like a great trip.


5k points for the trucker hats

Rebecca Meredith

I like the conclusion (it’s like Who’s Line is it Anyway – “all made up and the points don’t matter” 😉 everyone’s a winner – great job guys!

Mike DiNovi

Cop out, definitely!


Still literally laughing out loud at this.


I love the content. Makes me smile 🙂 ! I think a tie is fair even though I thought TYO was the better experience by a little. When is the best trip? How about RTW itinerary?


enough already, this is a “jump the shark” moment for FM

Tim Steinke

Now why didn’t we think of that for an activity? Next time.


So does that mean you are indeed sending it to overtime!?


Sure, both teams did great but IMO Team SFO should win by a landslide. Helicopter over the Igauzu Falls? Dining at the locals home? Painting murals on the streets of Buenos Aires? Is there even a question who should have won? I mean, Macao is very impressive destination too and it itself should be a a bucket list item. However, there was nothing memorable about the activities partook there, other than the hotel breakfast. That said, reading about the trip was so much fun. I keep announcing to my husband where the Party of 5 is now and what I think the next moves are. He looks at me like I am insane 😀 You have inspired me to travel more this year. And, I look forward to reading about your next year’s challenge! Thank you Greg and your Party of 5! This was a blast!


Great contest. I’ll be referring back to it for months.


Random question: You all ended the challenge in Iguazu Falls then had to get home (or wherever the FM nomads needed to be) from there. Did team SFO give anyone some lead time on that or was everyone stuck with whatever last-minute space they could find? Seems a bit tricky from a random small airport in the middle of South America.


Nice! Will we see a review/post of how each person got home?

Dugroz Reports

Both great, but by a small margin I’d vote for team Tokyo. I don’t enjoy overpacked days as much, and that B&B in the Philippines!!!


If I were ever asked to judge a judge (but who am I to do so! ) I would be curious to learn what stands behind the math for some of the point awards. Why would you award 15k vs 40k for lodging and 10k for big picture? What does each 5k stand for? Sensing a bit of a reverse engineering here to get to a tie, but, boy, I do not blame you! You are in the most tough spot as these were truly incredible trips!!!

But I do sway to team SFO by a small margin mainly because of the number of learnings for us, readers (which is why you do challenges!). I got a feeing that team Tokyo engineered most of their trip around Airbnb (which was incredible, but not enough) and then using FHR credit (?). It did not bring a lot of learnings for me as a traveler. I also felt their logistics of going places was super long and sometimes one would spend the whole day just in transit. Team SFO however, were able to showcase a great sweet spot (AS) and also brought very unique experiences, even sometimes in well-known places (like Irish coffee in SF).

I would totally be down to replicate many parts of team SFO itinerary, but the only true find in team Tokyo was, unfortunately, airbnb..

Michael DiNovi

Safety sways my vote: Team Tokyo


Since Nick has his fedora on in that picture, how did everyone know he was with the party of 5??! Where’s his team spirit?? Hahaha

Nick Reyes

I was trying to be certain that everyone knew it was me on the hat 😀


If they tied then I think it comes down to which trip you’d take if you could only choose one. Most families wouldn’t take two full week international trips, so which one of the two would be your first choice for your FM family to bond and enjoy together?


I had Team SFO winning it by a small margin.

– Both teams provided helpful insight with regards to flights (TYO with the difference in taxes between different types of Avios & SFO with the LATAM + stopover sweet spot).
– However when it came to lodging, I think SFO had the edge. TYO’s redemptions were great, but I don’t think I really learned anything (besides the cool Airbnb, which is great, but that knowledge doesn’t have much utility outside of that specific booking) and they ended up using a sizable amount of cash. On the other hand, I think SFO showed how you could use certificates and credits to really minimize your cash outlay for lodging, while still getting to experience some significant luxury.
– Both sides had great activities, but again, didn’t feel like I learned anything new when it came to TYO, whereas I learned about art tours and home dinners through SFO.

Again overall really enjoyed it, but had to give it to Team SFO!


Feels overly harsh to advertise bonus points for privacy, comfort and luxury, then dock points for booking business flights and three rooms instead of two. Were those redemptions/bookings unreasonably priced to deserve the penalty? I suspect if that had been clearer to Team TYO, they would have stuck to Holiday Inns and Jetstar/AirAsia to earn the frugality bonuses without getting budget penalties.

Likewise, it’s harsh to penalize Team SFO for planned but missed lunches that were not their fault (delayed flight arrival). On the other hand, lunches missed because of activity reshuffling to avoid bad weather are (unfortunately) deductible…

Last edited 3 months ago by vino

Can you give a breakdown for what the cash parts of the budget you listed includes? Curious whether the cash outlays came from taxes/fees on award travel, excursions /activities, food, etc. Also, it’s kind of ironic that most of the flight miles came from non-transferable currencies right? (AA (except Bilt) and Alaska) – can you explain that a bit more? It seems like points and miles blogs focus more on transferable currencies but the most value you got for flights were from non-transferrable ones. My personal experience is usually similar – I save a lot of transferable currencies and use them opportunistically (mostly air france / KLM or avios transfers) but I’ve subsidized probably 80% of my trips using AA, UA or Alaska exclusively and just build those stockpiles.

Also on podcast, Greg mentioned Team TYO didn’t give the chance for much local food. That’s a big miss for me and I think highlights the somewhat negative impact of staying at too resort-y places to maximize value of free breakfast etc. Was recently in Tokyo and did the same (too much lounge food, free breakfast buffet = less chance to eat local food). I was too focused on maximizing value and didn’t enjoy the local scene, hotel and food wise, as I normally would.

I also don’t understand the purpose or tone of the weird food challenge and don’t think any points should be given for that.

Tim Steinke

You can find the full cash breakdown of our cash spending for SFO here and for TYO here. That’s an interesting observation regarding transferable currencies vs. non-transferable. In this case, Greg has a lot of both and, for SFO, we were trying to prioritize using Alaska Miles that he had and wanted to use (and we also wanted to spotlight that particular sweet spot). My assumption is that TYO just found the best value currency for what they wanted to book and used that.

Still, your question/observation is a good one. While we all would, in theory, prefer transferable currencies (and that’s what I prioritize in my earning), generally, if I can use a fixed currency without a significant value drop, I usually will…and keep my more flexible ones in the bank.


Thank you!


How much of SFO’s hectic schedule and lack of lunch was due to unforeseen problems? Ubers not being what they were supposed to be, flight being late causing lunch to not be lunch, etc.?

I would probably prefer the pace of TYO’s trip, but I think I liked the actual activities better from SFO.

But, like you guys have said…thanks for doing stuff like this, it gives ideas for the future!


Tie seems fair. There were some great ideas from both teams. I might give SFO a tiny edge for having to navigate some, uh, less stable countries (as evidenced by your backpack disappearing), but overall it was really enjoyable to follow both adventures.

Neelika Choudhury

Team SFO had it easier. Harder to plan flights and activities from Tokyo. Also backpack. Team Tokyo should win.


I LOVED the whole challenge, especially as a mom just getting into the game with my own “party of five”. Loved the different types of experiences/transport/lodging showcased, the self-imposed budget, and even the completely different types of trips by the different teams. It’s clearly a very close contest by people’s (opposite) strong reactions to both sides! From a personal family-trip planning perspective, I would lean towards Team SFO’s trip. However, from a FM fangirl perspective, I think you have to give extra points for Team TYO’s constraint of having to get you back to Japan, which added transit/cut down activity opportunities.


Tokyo gets my vote.

Carl S.

Wrote a comment a little bit ago. It published. I edited a typo and then it flagged it as spam. Akismet was a miss on that. 🙁


To each his own as far as what is the “best” vacation experience, but personally I have learned that I don’t enjoy overpacked days. I want to have some interesting adventures, but not feel overly worn out at the end of every day. Tokyo gets my vote on this.

Carl S.

Regarding the Budget big-picture scores:

I think one of the main goals of Frequent Miler is to teach people how to use points and miles for things that would normally be cost prohibitive. In my opinion the thing FM seems to focus on the most is flying international business using partner sweet spots. My point being: comfort is very important. I do not personally want to fly in economy and stay in crappy hotels. I can do that without points and miles.

Therefore, I think that “penalizing” Team TYO for putting people in business class vs economy is wrong.

Also, you wrote “Team SFO wasn’t required to get us back home whereas Team Tokyo had to get us back to Tokyo. If Team SFO had been required to get us back to the U.S. and had used the same 45K per person Alaska award as was used to fly LATAM to South America, they would have spent far more miles than Team Tokyo. ”

To me that is HUGE!!! Team SFO basically got to fly you down to South America and leave you there. Otherwise their budget is way over Team TYO.

I think Team TYO deserves at least 10,000 more points in Budget big-picture.

I also agree that Team SFO not feeding you 3 meals a day should get some sort of bigger penalty on points than 5K.

Finally, maybe too much praise is being heaped on the graffiti activity. You wrote about it “making dreams come true” but that was only for one of the 5 people. Did it make dreams comes true for the rest of you?

I was thinking Team SFO would blow Team TYO away in this challenge but was pleasantly surprised by Team TYO. I have to give them the nod. (Sorry Nick and Tim)

Last edited 3 months ago by Carl S.

I agree on all counts. I had similar expectations before it started, but Team TYO should get the win for the reasons you listed.

Tim Steinke

It’s been interesting to see people’s responses to Team TYO having to go back to Tokyo. TYO had an extra day and a half, but had to get back to Tokyo, we had one and a half less days, but didn’t have to go back to SFO (primarily because of logistics). We all thought that was a fair trade, but that’s not how folks are interpreting it (which is a good lesson for us).

Had we had to plan our trip getting back to SFO, we certainly wouldn’t have gone to Chile, which is effectively what TYO decided to do by only doing three-ish hours away from Tokyo. We actually flew about 50% more miles than TYO, even though we didn’t have get back. Given the parameters of the challenge, it’s tough to say “they didn’t have to get back.” That’s true, but we didn’t have to…that wasn’t our portion of the challenge. Instead, we went further afield…which is what we were incentivized to do.

And keep in mind, the mural activity was meant for Carrie (we all had a great time), but each team member had their own targeted activity. Stephen’s was go-karts, brewpub and waterfalls, Greg’s was the private dinner. The mural workshop wasn’t intended to make everyone’s dreams come true…just Carrie’s. That said…everyone loved it.

As Nick said below, we actually did plan lunch for every day. The two days that worked were probably our best lunches of the trip (Sunday Brunch at Ritz Carlton Santiago and lunch at the Belmond Hotel at Iguazu Falls). We planned to eat in the Oneworld lounge at LAX on our first day, but we got there at 3:30 instead of 2:30 (due to a flight delay), so Greg said it was no longer lunch. We had a great lunch in the mountains planned on our second day, but that was cancelled after Greg’s backpack was stolen and he spent lunch time going around to different police stations. We planned to have empanadas before the street art class, but everyone ate breakfast late and wasn’t hungry. So, on us for poor execution, I guess. But it wasn’t left out of the plans

Last edited 3 months ago by Tim Steinke
Carl S.

You make some good points sir. Definitely gives me a different perspective on it.


I don’t know how your teams feel about it, but I’m fine with it being a tie. The goal of a vacation is to take home home fabulous memories and experience amazing things. At least, to me it is.

It appears that both teams did just that, and both very well. A tie, it is!


Although, like Tim and Nick I try not to eat three full meals a day, I think you probably did not dock them enough for not providing lunches. My understanding is that three meals a day was a non-negotiable rule rather than an optional points-earning activity. Also, not providing lunch allowed team SFO to plan more activities for which they got bonus points, thus negating even the small ding from not following the lunch rules.

Nick Reyes

You make a good point, Larry! I don’t really try not to eat three full meals a day, it’s just kind of how I end up rolling because I want to do X, Y, and Z and that doesn’t always leave time for lunch also (and I get far less hungry when I have a big hotel breakfast and then I’m on the move all day), but you’re absolutely right that it was a set expectation and more importantly, that skipping it allowed more time for other stuff. I hadn’t considered that to be an unfair advantage, but in hindsight you’re not wrong that it made it possible to pack in a full day of stuff.

In fairness, I think we expected to have enough time to eat in the lounge at LAX on the first day (and to have gotten there earlier than we did). In Santiago, we missed lunch because of the bag thing (and man was I glad that I had taken up LATAM on the 4am breakfast that I nearly skipped!) — we did have lunch planned after rafting had things gone according to plan. On the last day, we had planned for helicopter tour, then lunch, then boat — but as the weather forecast was calling for rain at 3pm, we went straight from helicopter to boat and only got to lunch around 2:15pm. At least on that day, we’d have had the same number of activities, but in a different order if not for the weather.

I don’t recall why we didn’t have lunch the day of the Santiago walking tour. That tour was at about 10am. I can’t recall why we missed lunch that day . . .

Tim Steinke

Well, as Nick said, we actually did plan lunch for every day. The two days that worked were probably our best lunches of the trip (Sunday Brunch at Ritz Carlton Santiago and lunch at the Belmond Hotel at Iguazu Falls). As Nick said, we planned to eat in the Oneworld lounge at LAX on our first day, but we got there at 3:30 instead of 2:30 (due to a flight delay), so Greg said it was no longer lunch. We had a great lunch in the mountains planned on our second day, but that was cancelled after Greg’s backpack was stolen and he spent lunch time going around to different police stations. We planned to have empanadas before the street art class, but everyone ate breakfast late and so wasn’t hungry. So, on us for poor execution, I guess.

But, we didn’t plan activities INSTEAD of having lunch. All the activities that we planned were planned around lunch.

Last edited 3 months ago by Tim Steinke

My comment was based on Greg’s summary in which, as I recall, he docked team SFO a small number of points for not consistently providing lunch. If you really did schedule three “square” meals a day but got done in be circumstances not reasonably within your control then maybe nothing at all should have been deducted?

Tim Steinke

I dunno. Greg’s a tough customer when it comes to lunch. 🙂


While there’s been many comments (and in the post) talking about how packed some of the itinerary became, it serves as a nice teaser for others to consider when figuring out what works for their families. Some are ready to go at a moment’s notice, while other families need creature comforts. Also, even though it was unfortunate, both teams faced hiccups and seeing how the family responded to “crisis mode” (as a group, or just 1 person) shouldn’t be discounted.

It’s also interesting seeing the difference in opinion here of what “vacation” means. Is it min-maxing your points (which tyo did better) or is it min-maxing the time you have around you (which sfo did better). Too often everyone is trying to redeem for ANA this or that Hyatt – are you actually carving your own experience or just doing what everyone else is already doing? Does that actually bring joy?

In the end, the challenge is about miles and points, so tyo should take this. I personally enjoyed sfo’s itinerary though. Hotels and flights blend together after a while, but I’m sure the light show, art, and iguazu experiences will still be talked about and shared between yourselves and your families.

Tim Steinke

This is a great point and something that we need to emphasize more when we’re doing these. We’re not trying to suggest that people should do our exact trips. We wouldn’t if we were actually travelling for fun. These are meant to be exactly what you say, ideas for what people can accomplish for points and miles…and ideas for what’s possible with 5 people.

Richard Mello

Good job! I really enjoyed following the challenge. With my real family of 5, the pace of the trip is important, so I would receive negative points for days like SFO planned. Great to see and hear that you guys had so much fun together!

Tim Steinke

Just replied to another commenter, that I think we don’t emphasize enough that we’re not trying to suggest that people should do these exact trips, but rather we’re trying to pack in possible options for what would be possible to accomplish with points and miles (in this case with a group of 5).

It took us two days of almost 12 hours of travel to get to and from that Airbnb in the Philippines. We would never do that and then just stay for one full day. Ideally, you’d go there and spend several days (which would have been fun, but wouldn’t have made for a very interesting challenge).

None of us would ever fly all the way to Chile and then spend 4 days in three countries back-to-back (heck, I would never spend under 2-3 days in Iguazu alone). But doing that helps us give readers a whole smörgåsbord of possibilities for their own trips…which is why we do these challenges in the first place.

Last edited 3 months ago by Tim Steinke
Beth B

I’m voting for team TYO. I like that they planned activities and downtime. Not feeling rushed and worried about getting from point A to B in a hurry is huge. Plus, they still offered awesome activities and unique experiences.


Honestly I think you should include some amount of weighting for the points. For instance, flights and lodging are more important (probably?) to the bulk of readers, as that is what these trips are for. So maybe weight those 35% each and then trail it down to 20% for activities, for food, food contest, or something. I think weighting is important to give proper importance to the things that are most valuable to the readers.


I’d give opposite weightings. Flights and lodging are just the “infrastructure” of the trip, it’s the food, activities, locations, and people that are the trip. I make an exception for the Philippines Air BnB which was a location unto itself.


Honestly if I showed up to a surprise location of that Philippines bnb I’d find a hotel. I was not into it at all.

But I see your point re: weightings. Greg probably needs to create a Google doc so that we can all go in and make our own weightings. I just wasn’t that into those activities. I get that they were tailored to the staff, but very few of those things were things I’d want to go and do so I would deprioritize them since it’s not a universal thing.


I think the personal chef at the air BNB very much mitigates the lack of otherwise interesting food offerings by TYO.


SFO has my vote for the unique experiences they found. Even if all activities would have worked out as planned, SFO still had the better ones. Thank you for highlighting South America!!
I love that you gave points for making the kids feel safe!!

It was fun to travel along with you. You are such a fun group I would love to travel with!!


Send it to overtime.


Truly LOL at the tie. 😀


Great job both teams!! It was a blast following along!
For me, I travel to far places to experience all I can, if I want to relax I just head to a relaxing (beach) place. So I enjoyed Team SFO a bit more, found their activities incredible (especially the Falls).
I know part of the challenge was finding great air/hotel deals for 5 but to me that is just transportation and a place to sleep at night. But thank you for showing us all what is possible.


I was following the Challenge from day 0, but at the end feel slightly disappointed by the hectic nature of packing way too many countries(cities) into both short trips. They both had a lot of transit time, check-ins plus packing-unpacking in each hotel, down time at each airport, … – you see the picture. Some people might like this type of travel for the sake of moving around a lot, but for me it takes a lot of valuable vacation time away from actually experiencing the places(countries) you go.

On the positive note, this challenge shows how one can use miles/points/credits in a effective way to make travel frugal and more affordable, specifically for a group/family of 5 persons. Both teams used imagination, skill and flexibility of various loyalty programs to assemble their itineraries. They also made a good food run by trying to stick to local eateries, and keeping everyone fed daily.

At the announcement of the Challenge, my thought were that each team will plan a few days at each starting location (Japan and SF) with just 1 outflying to a second location and back. That would’ve been more logical with 1st-class ANA seats to each destination (getting to destination refreshed and ready to explore). Instead main destinations were forgotten and both teams sped off to a totally different places for the expense of time, money, and energy. I was hopping to see interesting activities in Japan and around San Francisco, but it did not happen. The team’s names did not stand up for the challenge. Too bad for you guys and for the readers. It could’ve been a much more interesting experiences.

Iguassu Falls – yes, that is worth going for.
Flying around half the world for a Graffiti lesson or for a Go-cart ride – does not look reasonable to me. Overall both teams failed the challenge in understanding WHY to travel in the first place. Flying around is NOT traveling, it’s just flying around!

Previous Challenge was much much better. So go back to that type of world explorations, and make it interesting again, if you dare.

Nick Reyes

This is a fair piece of feedback, but I think it really speaks to the heart of the challenge that the way it turned out did not meet your expectations. Maybe we need to do a better job of the set-up so that everyone understands what we set out to do with a challenge. Tokyo and San Francisco were the starting points for each team, but the expectation that we’d stay there instead of showcasing a miles and points opportunity to go somewhere from those starting points tells me that we should have done a better job on the front end of setting expectations.

We are primarily a miles-and-points blog. For us, the key focus is in showing people how to get to places (flights) and stay affordably (hotels). Obviously we *also* wanted to showcase why you might want to go to those places by showing some awesome activities and having fun with a group, but this isn’t a primarily travel channel-esque blog, so it is unlikely that we’ll run a challenge where we’ll fly somewhere to stay in one place for four or five days showing you all of the activities you can do in that one primary location — and that’s not because we don’t want to fly places and do things, it’s just because day after day of activities in one spot would mean little miles-and-points / credit card perks content (there is only so much to write about stacking a deal at Viator, and otherwise, using points and miles for activities is almost always a very poor value). Since the focus of the blog is ways to earn miles without flying and then the best ways to leverage those miles, I think our challenges will likely always feature a faster-than-average pace in order to be able to showcase several sweet spots in one trip and draw your attention to opportunities that you can leverage for trips of your desired length. That’s our wheelhouse.

That’s not to argue that you shouldn’t consider the pace of travel in determining the outcome, and I agree that there is value in building in time for relaxation, but I think by design we are always likely to have more time spent in transit than you would want if you were traveling with your family. I’ll travel a lot slower on vacation with my family next week, but I probably won’t write posts about our daily trips to the gelato shop or museums we visit or that type of thing just because that isn’t our primary focus on this site. I probably will write a bottom line review of the flight and hotel because those are the things pertinent to this site and our readers, and I may pepper in some details about stuff we did to say why you might find it worth staying there, but we haven’t historically focused much on activity-related content aside from those handfuls of activities that we do during these challenges, each of which is meant to give a sense of some local flavor that mattered to us (and certainly may or may not matter to you). Each team obviously did want to plan activities to showcase why we chose our destinations and/or build in enjoyment for everyone, but the primary focus for us wasn’t to take a singular trip to master a singular destination. I guess in my mind that type of travel is the Rick Steeves realm and the miles and points stuff is the Frequent Miler realm. Our challenges are likely to incorporate a smaller amount of Rick Steeves and a greater amount of Frequent Miler (if that makes sense?). I think I hear you saying that you wanted more Rick Steeves, and that’s a good piece of feedback (and I’m glad if you enjoy watching us interact with more travel-based content). I’m not arguing that we shouldn’t incorporate more of it, just saying that I think the balance is likely to always be tipped toward more Frequent Milery content. We did talk during this trip about doing more regular short Frequent Miler team trips — like where we go somewhere for 3 or 4 or 5 days together to showcase one particular sweet spot hotel or airline redemption, mostly because we enjoy traveling together — but on challenges I think the heat will always be on to showcase a few cool redemptions in whatever amount of time we have over showcasing all activity content.

Again, all of us travel at a slower pace when we go on vacation than we do on the challenges. We don’t design these challenges to create a timeline that you’ll want to replicate but rather to show off some techniques we use that you can apply to your trips of days, weeks, or months longer than ours (depending on your time flexibility and desires) and/or to one or two of our destinations (recognizing most readers won’t want to see all of them but may find one or two or three that they want to see). The one way in which the challenges do replicate how I travel is that I no longer feel a need to do everything in one place before moving on. The beauty of miles and points is that I always know that I can go back, so I don’t emphasize having to do everything and instead focus on a couple of things with the full knowledge that I’ll get there again if I want to.


Hard disagree on the original comment and hard agree on Nick’s reply. It’s nice to see the videos and pics of the team’s fun world adventures, but the central purpose of this challenge is just that — it’s a *challenge* centered around the redemption of miles/points/frequent traveler perks. In order to showcase that, you sort of do need to just fly around and stay in hotels just for the sake of it.

(Edit: Ok, maybe not “hard” disagree on the original feedback. The schedules were indeed very hectic, but if the teams had overall been less active, then we, the readers, would have been provided far less overall content for using miles/points as well.)

Last edited 3 months ago by Shogo

Nick, thanks for reply, and I get your point of view on this. But I can point out, the name of your blog is “Frequent Miler – Earn Miles Without Flying”, so you guys may not fly at all judging by it. 😉

But as I see it, the main drive behind FM is to inspire travelers by showing them what’s possible to do with miles & points, and moreover what’s worth pursuing in this hobby: great natural and man-made places to see, various cultures to experience, different food to try, etc. – all while be creative and frugal about ways to pay for such trips.Otherwise it can become a purely technical info-blog as it’s name suggest…

Great example I can give is “Travel is Free” where Carrie played a big role creating. It gave a ton of information about best ways to use miles/points, while giving the reasons and inspirations for going places. Places and experiences are what drives the travel, and not miles balances, transit time, and seat reviews. Something to contemplate about (by the way, I don’t like Rick Steeves style you suggested).

With all being said, both teams in this Challenge did a good job on earning points for the bookings and activities. But skipping major stopping places on the route, like Japan and Hong Kong, are counted as a missed opportunities for me.

Happy travels!!


I’m sympathetic to both your points (that there was way more “motion” than I’d want on a trip, and that the focus wasn’t on the “original destinations” of Tokyo and San Francisco).

In terms of how much moving around there was, I think you need to look the competition sort of like one of those cooking shows in which they put the food into the oven and, in the same motion, remove a dish that’s already been cooking for hours. In other words, they accelerate stuff for the sake of keeping the action going. You or I (and probably the actual Frequent Miler team), if doing this as a real vacation, would probably spend four or five nights in the Philippines, three nights in Macau, and a week in Tokyo. Same for the South America itinerary.

In terms of basing the trips in Tokyo and San Francisco, while that’s more realistic, it’s not really in sync with the Frequent Miler blog. They could have focused on “interesting” hotels (to the extent that you think hotels are interesting) but FM isn’t really a blog about food or culture. I think they touched on a lot of that in the competition, especially the idea that you want to include activities targeted at each individual person but enjoyable by everyone else. But, ultimately, most of the points-earning items on Greg’s list had to do with points and miles and for that flying and changing hotels is required.


I think the winner was clearly Team TYO. The challenge was how to get 5 people to interesting places using points and miles. Many times it is mentioned that this might be a family. If this is the case-then Team TYO did a much better job thinking about food options, transportation, activities, and downtime compared to Team SFO. I would include negative points for not considering having the Ritz send transportation to the Santiago airport for pickup of 5 people–which was always going to be a strain on Uber and likely safer option for getting 5 people around. Even though eating with a local family in Argentina was a cool idea that seems like also the only time you really got local food on that part of the trip and relied mostly on granola bars. The lack of downtime on the Team SFO side seem to mean no posting of the challenge on any of the social media sites. So for long periods of time you could not follow the challenge in South America whereas it was close to “real” time for Team TYO. As a reader the second part of the challenge wasn’t as interactive or enjoyable as the first part and we are just now getting videos of that experience. Overall, this highlighted many cool things in both locations and new things to try out and places to see. Both groups did an amazing job with the resources-but Team TYO had an itnerary that was closer to what you might do with a “party of five” in tow and those of us following the challenge could be more engaged in real time with what was happening.

Nick Reyes

Just regarding getting transport from the Ritz: That was an option, but not one that we seriously considered because of the cost versus doing it on our own. I can’t recall the pick up cost, but the drop off cost for the Ritz to bring us to the airport was $120 — versus I believe the Uber was $10 or $15? We had requested an Uber XL, it just wasn’t very XL. We initially thought we’d do two cars (both Tim and I requested Ubers), but pick up time was slow and when the first one showed up we figured we could probably all get in one. I could certainly see someone choosing to pay the extra to get the Ritz car, or getting two Ubers, just responding to say that it was something we considered and decided not to do.


I have to agree with the tie. Both teams did an amazing job with the constraints given and the obstacles faced. I loved following along and checked IG constantly for updates!


Bonus points needed for whoever came up with the hat. It’s so bad it’s good, took me back to 1985 and every hat I wore back then. And speaking of the hat, what are the chances of getting one?

Rachel Raz

I’m for leaving it a tie! I see amazing innovation and finds in each group. Nothing stands out as “better than the other by a long shot”…


Culturally, Team SFO won hands down. The in home dinner and street artist activity by far were the two most meaningful parts of the entire trip. Sure the flights and hotels are important, but aren’t they a means for having great experiences where you go?


I don’t even see how this is close. Tyo clearly won bigly, in fact, I think you’re kind of changing your “rules” regarding having a nice vacation. Tyo was more of a vacation, not hectic running around. You said you valued privacy and not cramming everybody all together… clearly tyo did that better both in the ground and in the air. Not really sure how you can take off points for budget from them, they clearly were very frugal and you didn’t set a hard budget. They also obviously spent way more time and I feel that there was some innovation with theirs in terms of the airbnb. I don’t remember any innovation, new discovery, secret spot with sfo.

Tim Steinke

Just replied this exact thing to another commenter, that I think we don’t emphasize enough that we’re not trying to suggest that people should do these exact trips or that the goal of the challenge is a nice vacation for us, but rather we’re trying to pack in possible options for what would be possible to accomplish with points and miles (in this case with a group of 5).

It took us two days of almost 12 hours of travel to get to and from that Airbnb in the Philippines. We would never do that and then just stay for one full day. Ideally, you’d go there and spend several days (which would have been fun, but wouldn’t have made for a very interesting challenge).

None of us would ever fly all the way to Chile and then spend 4 days in three countries back-to-back (heck, I would never spend under 2-3 days in Iguazu alone). We did it to spotlight the Alaska Sweet Spot on LATAM with the free stopover. Doing the challenges this way helps us give readers a whole smörgåsbord of possibilities for their own trips…which is why we do these challenges in the first place.

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Fun! Shouldn’t the free night certificates be factored into Team SFO’s total spend?


Leave it a tie…and give gift cards to each team member and their spouse to go out on a date night to a nice dinner and movie.

Tim Steinke

Now you’re talkin’!


CIC 5X at Staples…Greg gets the points. It’s a win-win.

Tim Steinke

Preach it, brother!

T. Jones

I won’t disagree with you or try to convince you otherwise on your scoring. However, I simply ask you to consider my suggestion in the comments of an earlier post. If you agree, then Team SFO should receive bonus points for engagement. I forgot exactly how many points I had previously suggested, but the amount doesn’t really matter. What’s important is that it would tip the scales in their favor ever so slightly, giving Team SFO the win.
Congratulations to all for sharing your amazing travels!


I think you need to give Nick at least 5 extra points for finding a car and running around with you trying to find your backpack. 🙂


Hard to know what to do with activities not completed. I think the rafting & hot springs might have contended for the best day of the whole trip (based on my own time in the Andes), which wasnt done at no fault of team SFO.

Weather ruining the Macao day was similarly bad luck for Team Tokyo. Maybe its tough to give SFO too much of a bonus credit here since both teams had a day lost, but its good to plan a mix of indoor and outdoor activities for backup plans, so maybe TYO couldve done better having a weather contingency where the backpack theft wasnt really something SFO could’ve planned for.


As someone who came back from Hong Kong 3 days ago and endured the pouring rain through my whole stay there, I feel for team TYO but come on, Nick at least found a car. 5 points is all I am asking for 🙂

Nick Reyes

I want to hop in to say that I didn’t find the car. The Ritz offered that up as Greg was talking to the concierge about following up with the police. I did ride around with Greg and get a tour of the Santiago police precincts and less touristy neighborhoods and got locked in the back seat of a police cruiser with Greg, but I didn’t find the car.