The Frequent Miler team is preparing for our next challenge! This year we’ll compete to see who can book the most amazing 100,000 point vacation. This challenge is a nod back in time to our first ever team challenge — 40K to Far Away. That was a one-way challenge where we competed to see who could go the farthest with 40,000 points. And we went really far (view the summary results here), but we sacrificed comfort. We flew economy, and we slept on benches, buses, and in couch-surfed homes. This time, the goal is to travel round-trip, to sleep at least 3 nights in comfortable lodging, and to do it all with as much style as we can. Travel will take place in the fall, but we’ll be scheming (and reporting on our scheming) until then.
Why 100K?
The “100K” part of this challenge was inspired by the 100K Chase Sapphire Preferred offer that expired in May. Nick previously published some ideas about how to use 100K points (A trip to Europe for two people with just 100K points), but now it’s time for us to put our 100K points into action to show what can be done not just hypothetically, but with real travel.
But the contestants won’t be using Chase points. Instead, I’ll use Chase points to set the standard that everyone else aims to beat. The contestants will then try to beat my trip (and each others’ trips) with Amex points, Citi points, or Capital One points…
The 100K Benchmark Trip
I’m not a contestant this time… not really. Instead, I’m going to travel before the other contestants to show off what can be done with 100,000 Chase Ultimate Rewards points. We believe that Chase points have a big advantage in this challenge over other points — namely, the ability to transfer 1 to 1 to Hyatt*. Since the trip must include at least 3 nights in hotels, the ability to book Hyatt stays for as few as 3,500 points per night should be a huge advantage.
* Note that Bilt points have the same advantage but we’re not including Bilt in this challenge due to the large overlap in transfer partners.
Three Challengers, each with 100,000 points
Tim, Stephen, and Nick will be the challengers this year. Each picked the transferable points they wanted to use for this challenge (but note that Bilt points were not allowed since Bilt’s transfer partners overlap so much with Chase’s). Here are the points each challenger picked:
- Tim: Citi ThankYou Rewards
- Stephen: Capital One Miles
- Nick: Amex Membership Rewards
After my benchmark trip is over, the three challengers will launch their travels at roughly the same time. As usual, our trips will be revealed in near-real-time on Instagram, through daily blog posts, and through occasional livestreams on YouTube.
Two Judges
Carrie and I will judge the three contestants. We’ll award points for style, affordability, unique-leverage (i.e. we’ll favor the use of unique aspects of each transferable points currency), and applicability (i.e. we’ll disfavor uses of points that aren’t of much use to many people).
We’ll also award bonus points for mini-challenges that will be revealed later.
And while specific details haven’t been entirely worked out yet, we plan to include audience feedback into the scoring.
$1,000 cash budget
In addition to the 100,000 point budget, each contestant will be limited to spending no more than $1,000 out of pocket. This includes everything: taxes, surcharges, Ubers, meals, outings, etc.
When a contestant earns a rebate of any kind, that will not expand their budget. Instead, it will help them earn points when we judge them for affordability. For example, suppose a contestant books a $200 day-trip tour and gets back $50 from a shopping portal. In that case, they need to account for the full $200 towards the $1,000 cash limit, but when we score them for affordability, we’ll factor in the rebate.
Rules 
- Each vacation must involve round-trip travel
- Contestants can start wherever they want as long as they return back at the end (but contestants should keep in mind that the judges will prefer trips that could reasonably be booked by many in our audience)
- Each vacation must include a minimum of 3 nights in comfortable lodging (and bonus points will be given for longer stays)
- The budget is 100,000 transferable points + $1,000 cash (contestants should keep in mind that the goal is to show how much can be done with 100,000 points, so the more that is covered by points the better)
- The budget covers everything: travel, food, activities, taxes, surcharges, bribes, bail, etc.
- No cashing out points. The goal here is to demonstrate great uses of points, not cash bargains.
- Rebates do not change the $1K limit on how much you can spend (but may gain you affordability and style points)
- All transfer bonuses during the travel planning phase are fair game (and don’t need to be declared in advance)
Audience Participation
We’ve started kicking around ideas for how best to include our audience in this challenge. Here are some of the ideas we’re considering:
- Voting: Audience polls will help determine the challenge winner
- Advice: Audience members will be able to give advice to any one of the challengers to help them ace their vacation.
- Mini-challenge ideas: Audience suggestions may determine what kinds of mini-challenges the contestants will face in order to earn bonus points during their travels.
- Theoretical challengers: Maybe we’ll offer a way for people to submit their own theoretical vacation plans using no more than 100,000 transferable points.
- Travel challengers: Just for fun, we may provide a way for people to compete with us, sharing their own real live travel.
Other ideas? If you have ideas for how we can include readers like you in this challenge, please comment below!
Greg’s Take: Who will win and how?
All of our team challengers have access to a number of great airline transfer partners, so I’m guessing that the bulk of each person’s strategy is going to revolve around how they’ll book hotels. Let’s look at what each contestant has available in that regard…
Tim: Citi ThankYou Rewards
- Leading Hotels of the World (5 to 1 ratio)
- Accor Live Limitless (2 to 1 ratio)
- Wyndham (1 to 1 ratio)
- Choice (1 to 2 ratio)
- Preferred Hotels & Resorts (1 to 4 ratio)
If I were Tim I’d be looking very closely at Preferred Hotels & Resorts which start at 15,000 points per night. If Tim finds a great resort bookable at 15K I Prefer points per night, that will cost him only 3,750 Citi points per night thanks to the 1 to 4 transfer ratio. So, he could stay 4 nights for only 15,000 Citi points!
Stephen: Capital One Miles
I was really surprised that Stephen chose to go with Capital One Miles. I think that’s a tough one for hotels:
- Accor Live Limitless (2 to 1 ratio)
- Choice (1 to 1 ratio)
- Wyndham (1 to 1 ratio)
Citi offers all of the above, plus Choice at double the transfer ratio, plus other hotel transfer partners. I think that Stephen’s best bet is to find a hidden gem in Wyndham. Wyndham has a few opportunities to book great properties for 15,000 points per night (including vacation homes in England, via Cottages.com). A three night stay will cost Stephen 45,000 points (actually, a bit less if he leverages his 10% Wyndham Earner card discount by calling in the booking), so he’d be looking at spending 40,500 points for three nights. That will leave him with nearly 60,000 points for round-trip travel. That might just be enough to do something really interesting!
Nick: Amex Membership Rewards
Amex’s hotel situation is really bleak:
- Choice (1 to 1 ratio)
- Hilton (1 to 2 ratio)
- Marriott (1 to 1 ratio)
The advantage Nick has here is that Amex runs transfer bonuses frequently. If he can score a 30% transfer bonus to Hilton, he might be able to make some magic. For example, suppose he finds a nice Hilton bookable for 30,000 points per night. With Hilton’s fifth night free benefit, he could book that for 120,000 Hilton points. With a 30% transfer bonus, he could get enough points by transferring 47,000 Amex points to Hilton. That would leave Nick with 53,000 Amex points for his round-trip travel. And if he takes advantage of transfer bonuses to airline miles, he might be able to turn those 53,000 points into 68,900 miles. All of that said, don’t expect Nick to do the expected. He’s the guy that found the incredible deal for flying to Hawaii dirt cheap with Turkish miles during the first team challenge. He’s also the guy who found a way to use Avios to book Scandinavian hotels dirt cheap. And, of course he’s also the one who managed to turn status matching into a life at sea via free cruises.
My Bet: Who’s going to win?
I’m going to go all out with the benchmark trip to make it as good as possible, but I’m hoping that every one of the challengers will beat that benchmark! That said, there can be only one [winner]. The odds-on favorite here has to be Tim. He has a plethora of options for hotels, and Citi is known to do regular airline transfer bonuses too. Don’t count Stephen out, though! Stephen has lived in hotels and vacation homes for the past 8-ish years and therefore has more experience booking hotel deals than the rest of us combined. I’m expecting him to come up with something really cool. All of that said, Nick hasn’t won a challenge since 3 Cards, 3 Continents in 2022 and he’s chomping at the bit. I can almost guarantee that he’s going to make some 100K magic happen in a way that no one can predict. Despite the odds, my bet is that Nick will take home the crown.
Who do you think will win? Comment below.
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I really like the set up on this particular challenge, but I would make one change. One of the real advantages with having points is being able to leverage your cash when you need to and or your points when you need to. By limiting, especially Stephen, from being able to use cash in the hotel category the overall trip might get slightly, or not so slightly diminished using the same points and cash budget. This one modification would make the overall competition more interesting – I mean at the end of the day we’re only talking about a $1,000 budget.
I’ll definitely be using the challenge criteria to figure what trip I could take with the given points and look forward to watching!
Will contestants have to announce when they do a points transfer or at least send a note to Carrie (as the judge who isn’t participating in the travel)? This way, it better simulates the real world in that the contestants can’t book a flight/hotel now while there is better availability, hope that there is a transfer bonus to that program between now and departure (maybe there historically has been) and then retroactively claim the transfer bonus.
I think Greg is going to be hard to beat because of the low cost of Hyatt stays at some fun places with cheap food. 5 nights at a 5,000 point per night hotel is only 25,000 points.
For example, unfortunately, the transfer bonus to flying blue just ended. If Greg flies roundtrip to Vienna from JFK for 75,000 Flying Blue points and then stays at the Lindner Hotel Bratislava for 5 nights, he can optimize his 100,000 points. The train ride from Vienna to Bratislava is cheap ($16) and food in Bratislava is relatively cheap (which offsets the expensive fees and taxes on Flying Blue). For example, this blog post outlines some cheap eats in Bratislava.
The one question is whether Greg is allowed to take advantage of a Globalist status /a Guest of Honor Cert for free breakfast to conserve his food/entertainment budget. Still, I’m pretty sure he could eat fairly well in Bratislava for a week on the money left over after his Flying Blue taxes and fees.
I think Greg is right that Citi points are probably the best option in terms of flexibility for hotels (I have a favorite unsung spot for an LHW property that’s pretty amazing). However, I think C1 points might be sneaky good. There’s a lot of weird sweet spots in the C1 partners once you leave North America. This could be a cool challenge.
I REALLY like that this year’s challenge appears to be more hotel stay-focused rather than air travel-focused. While award flights will certainly have their redemption sweet-spots and variations that you can get creative with, for the most part it’s rather predictable and can get repetitive. For hotel stays, however, there’s a bottomless well of lodging options and redemption tactics to learn about, and loyalty programs really are evolving at a very rapid pace, so I’m really excited about this one! Excellent choice on the $1000 budget to go along with the 100k.
The post was indeed pretty hotel focused, and 100k is probably too limiting for business award travel, but there are some unique opportunities for each:
Citi: EVA (better transfer than C1), Turkish
C1: Turkish, TAP Air Portugal, EVA
Amex: ANA (one way awards soon), Hawaiian/Alaska (soon dead)
Is it that time of year already? How exciting!
My favorite time of the year! It seems like you see this as a primarily hotel-focused competition, is that your thinking?
Rules clarifications:
What does Each vacation must involve round-trip travel mean? Does it have to be air travel? To a different country? Or could someone hop on a train to the nearest city with a great hotel and good restaurants? For instance, could Nick hop Amtrak down to NYC and vacation there? Or Stephen to London? Or Tim to Walla Walla?
If you can decide the start and end point, could you place that strategically with respect to your vacation destination? Like, if someone’s vacationing in Cairo could they make Doha their start/end point in order to take advantage of the first class awards on Qatar? Or, if someone is targeting New York, could they make their start/end point be JFK? Or Grand Central Terminal?
I’m not sure about the “applicability” juding criteria. It seems very subjective. If you’re really talking about the broad general public they want to go to European capitals which, while broadly applicable, might not make for the most exciting or interesting competition.
Actually, thinking a bit more about the “applicability” judging requirement, I know that you guys based your RRV mostly on domestic travel since you feel that’s what the largest part of the reading audience is interested in, so wouldn’t that favor a major East Coast (for Nick), West Coast (for Tim), or UK (for Stephen) destination?
Round trip travel just means getting back to the city in which we started, rather than like 40K To Faraway where we didn’t have to make it back. We’re basically trying to make it realistic – that someone going on vacation who wants to use their stash of 100k points would need to get back home at the end of their trip.
However, we do all have to fly somewhere and we can only use our miles to do that, rather than finding a cheap cash flight, mistake fare, etc. We can include a train journey, ferry, etc. as part of our trip if applicable, but the vast majority of our travel has to be flights and accommodation that are booked with 100k points and 100k points only (other than taxes/fees on award flights).
With regards to start and end points, we’re doing that based on us all originating in the US seeing as that’s where most FM readers would be setting off from. However, Nick doesn’t necessarily have to start in New York despite that being his closest major city and Tim doesn’t have to fly out of Seattle necessarily.
With regards to applicability, that’s more in the sense of planning a trip that can be easily recreated by readers if they wanted. So although it might be great to be able to book some kind of super-cheap award that was only available for an hour due to a mistake by a loyalty program, that’s not broadly applicable as it was a one-off. Similarly, Nick’s one-way Aeroplan itinerary during the 3 Cards, 3 Continents challenge was incredible and definitely deserving of the win, but it wouldn’t be great for this specific challenge as people are less likely to want to replicate that kind of trip themselves. However, Nick using Hilton’s 5th night free benefit during this challenge on the other hand is much more applicable, even though it does require Silver status at a minimum.
One of the many things I love about Frequent Miler is using RRV to help decide whether or not the redemption I’m about to make is “worth it”. Currently, RRVs stand as follows:
Given these RRVs, is it therefore reasonable to to expect more from Nick or less from Stephen? To be fair, my math would indicate just a 3.33% advantage/disadvantage from Tim’s Citibank point of view.
I think those RRVs heavily reflect airfare redemptions and this seems to be a more hotel-focused competition (it’s not even clear to me if air travel is an expected or required part of the competition). So the RRVs might need to be different, excluding airline partners, to rank the competitors’ chances.
Hotels will – in theory – be the most challenging part of this seeing as we need to book at least three nights in accommodation. However, booking flights will also be challenging seeing as we have to get both to and from our destination while leaving enough points to also have somewhere to stay.
I love your challenges and I am extremely excited for this one! I feel like it gives your readers 4 very realistic examples of what someone could do with just one SUB (or possibly 2 SUBs, especially in the case of Citi).
As someone with a spouse and a kid, I’d love to see a future challenge incorporate family travel.
Seconded. We’re a family of four with our two little ones being under 7 years old. Nick provides a lot of insight regularly on this type of travel, but it’d be a fun challenge to see what creativity they can do when bound to a school schedule.
I love these challenges, and this one looks good. 100k plus $1000 is a real-world budget, and I think that will engage the audience. A lot.. who knows, I might even be a play-along contestant…
Affordability, unique-leverage and applicability are good judging criteria. Those categories hit your core FM objective of delivering tips for stretching award redemptions for maximum value. Those types of scoring criteria are also why the past challenges have resulted in so many enduring strategies.
I have a concern, though….If style points are judged in a way that rewards upgraded flights and swanky lodging, will the underlying purpose of travel – the destination, the sights, the food, the people, experiences – be effectively squeezed down to just an incidental scoring criteria?
I’m thinking the contestants might incentivized so strongly toward amazing value for flights and lodging that there is a risk that the winner’s trip won’t be one that I would like to take. I.e. a three- or four-city tour over long distances riding in a nice seat just to hang out in fancy hotel suites might score at the top. It would illustrate great value for the transportation and the stay, but not be reflective of the core reasons I travel.
Your game, your decision, and I recognize there are shades of gray here, but please consider bit more weight on the destination and non-airplane, non-hotel activities.
There are several way you might do it: high-value challenges related to ground activities that effectively become a tie-breaker, splitting the style category so air+hotel are separated from everything else….etc.
Your concern about the de-emphasis of the actual travel destinations is legitimate. But this isn’t really a blog about travel per se, it’s about hotel and airline points, and so it’s natural that they concentrate on airline and hotel experiences. There are limited ways (but there are some!) to use points to obtain broader “experiences” — and always the philosophical question “is an experience you pay for really an experience, or just a simulation of one?”
That’s definitely a legitimate thing to consider. Although flights and accommodation will be a significant factor in the judging, I think this challenge will likely incorporate far more destination and activity-based contents than our previous challenges. In the past, we’ve often had to fly quickly from place to place due to the nature of the challenge, budgetary restrictions, etc. However, with this challenge the purpose is to show the kind of vacation you can create with 100k points + $1k cash, so that will inevitably include more of the destination itself. Hopefully we’ll be able to get a good balance 🙂
Greg and Carrie will also be setting us some random challenges which I imagine will be destination-based rather than related to our flights and/or hotels.
Absolutely love these challenges. It’s the creativity – I feel like you guys always find at least one “new trick” when you get tested like this 😉
Thanks Dave!
I’m stoked for this, especially to see what Stephen does to get inspiration for what to do with my C1Vx points
Not a fan of FM contest content, I rather read normal everyday content
One of the good things a blog/podcast can do is provide varied content because there’s no one thing that ALL consumers like. They write a lot of articles on deals/ maximizing points/etc and make the podcasts/youtube show; this is just another way to appeal to viewers in a different format.
I believe that Frequent Miler has recently liberalized their terms and conditions, and you’re no longer required to read the posts that are not of interest to you. I love these challenges and I think the (large) majority of other readers do as well. FM has plenty of content that doesn’t interest me personally but that I presume other people follow — I don’t feel compelled to criticize them over that.
Haha, love this “I believe that Frequent Miler has recently liberalized their terms and conditions, and you’re no longer required to read the posts that are not of interest to you.”
I suggest bonus points for rhyming. Like anybody who could book the “100k Cathay JFK Taipei railway AAA farm-stay gourmet buffet vacay” would get my vote even if they slept on the floor.
Love it!
Love it #2!
Hey, okay! Way to play!
LOL!
Yes!!!