Frequent Miler’s latest team challenge, 100K Vacay, is done. The goal (which was handily achieved) was to create an incredible vacation with 100,000 transferable points and a $1,000 budget. And that budget had to account for everything from flights to lodging to meals to local transportation to entry fees to… You get the idea. You can read the original announcement and rules here.
For this challenge, Carrie and I served as judges, while Tim, Nick, and Stephen were the contestants. Sadly, Tim had to drop out early due to a family emergency, so the competition came down to just Nick vs. Stephen. Tim will separately post the details about the incredible trip he had planned.
Want to vote for your own winner? Click here to jump to the audience vote!
Trip Summaries
Read below to learn about each of the 100K Vacay Trips. Or, better yet, check out these daily recap videos:
- 100K Vacay Day 1
- 100K Vacay Day 2
- 100K Vacay Day 3
- 100K Vacay Day 4
- 100K Vacay Day 5
- 100K Vacay Day 6
Greg’s Benchmark Trip
We believed that Chase points had a huge advantage in this challenge over the other transferable points we used because this challenge required using points to stay at least 3 nights in hotels. Chase’s ability to transfer 1-to-1 to Hyatt, along with Hyatt’s excellent award chart in which free nights start at only 3,500 points off-peak, would have given a competitor an unfair advantage. Therefore, we removed Chase from the equation by making it the benchmark currency. Before anyone else travelled, I used Chase points to build a benchmark vacation that we would use to more effectively grade the challenger trips.
Budget: 100,000 Chase Ultimate Rewards points + $1,000
Amount Spent: 97,000 points + $968
Cash Value of Trip: $4,341
This is likely to be an inflated number since it uses the cash price of the exact flights and hotels booked, rather than considering that one may have booked different flights/hotels with cash.
Trip Theme: None
Trip Summary: I started my round-trip journey in Detroit. I flew business class to Malta and stayed 4 nights at the excellent Hyatt Centric hotel. In Malta, I enjoyed great local food, multiple tours, and multiple outdoor activities. Return travel included Virgin Atlantic premium economy from London to New York. Full details can be found in my challenge journal.
Nick’s Trip
Budget: 100,000 American Express Membership Rewards points + $1,000
Amount Spent: 100,000 points + $979.63
Cash Value of Trip: $3,973
This is likely to be an inflated number since it uses the cash price of the exact flights and hotels booked, rather than considering that one may have booked different flights/hotels with cash.
Trip Theme: Bond, James Bond / Casino Royale
Nick started his round-trip journey in Boston and flew economy on all of his flights. He flew first to Málaga, Spain, where he stayed one night at the luxurious Palacio Solecio SLH hotel and spent his second night at the Hilton Garden Inn Málaga. Nick went full adventure-mode in Malaga, first with his Caminito Del Rey hike (pictured above), followed by windsurfing lessons! Nick then flew to Belgrade, Serbia, where he stayed at the Saint Ten Hotel (another SLH property). In Belgrade, he met up with an old friend who gave Nick a tour of the city. Together, they ate at a fantastic Serbian restaurant. But Nick wasn’t done… He next flew to Sofia, Bulgaria, where he stayed two nights at the Hilton Sofia. Nick’s reason for visiting Sofia was to enter a two-day poker tournament! During poker breaks, Nick managed to fit in a walking tour and some local eats. Sadly, Nick didn’t win the tournament, but he had a great time.
Read all about Nick’s trip in his journal, here.
Stephen’s Trip
Budget: 100,000 Capital One Miles + $1,000
Amount Spent: 89,900 points + $928.31
Cash Value of Trip: $3,622 + $590 (the value of Shae’s travel obtained w/ Stephen’s points)
This is likely to be an inflated number since it uses the cash price of the exact flights and hotels booked, rather than considering that one may have booked different flights/hotels with cash.
Trip Theme: Beer cheers!
Stephen started his round-trip journey in New York and flew economy on all of his flights. He flew first to London, where he stayed one night at the Ibis Heathrow hotel. In London, he enjoyed an all-day beer brewing experience. Next, he flew to Munich, where he stayed two nights at the Ramada Encore by Wyndham Munich Messe. In Munich, he fully immersed himself in the final days of Oktoberfest: eating, drinking, and even singing along with the crowds. Next, he took a bus to Prague, where he stayed two nights in the Clarion Prague’s top-floor suite with an enormous balcony overlooking the city. In Prague, he ate at a fantastic local restaurant, explored the town, enjoyed the Pilsner Urquell Experience, and relaxed at a beer spa! The incredible thing about Stephen’s trip was that his wife, Shae, accompanied him the whole way, and he accounted for her travel expenses under the same 100,000-point budget! Note, however, that her cash budget was separate.
Read all about Stephen and Shae’s trip in Stephen’s journal, here.
Scores
Scoring Categories and Scale
Since we love acronyms, we crammed all of the scoring elements into five major categories to spell “WAVES” (as in, we’ll see who made the most waves in this competition… yes, groan).
- WOW (18 possible points)
- Subcategories: Location, adventure, relaxation, food, local exposure, out-of-the-box ideas
- Applicability (18 possible points)
- Subcategories: Replicability, applicability
- Value (18 possible points)
- Subcategories: Dollar value, frugality, pro behavior
- Extras (28 possible points)
- Subcategories: Budget, # nights lodging, check-in attendance, daily post updates, secret destination
- Style (18 possible points)
- Subcategories: Luxury flights, luxury accommodations, other point-driven luxury
Because the competitors were trying to beat my benchmark trip, we’ve structured the points to reflect not only whether they’ve succeeded at a particular goal, but how elements of their trip compared to mine.
For example:
- 0 points – The traveler did not meet this target as well as Greg
- 1 point – The traveler met this target at least as well as Greg
- 2 points – The traveler met this target better than Greg
- 3 points – The traveler met this target better than everyone
(To make sure each subcategory is weighted according to our notion of its importance, sometimes this scale uses higher increments of 2 or 3.)
Final Scores
Carrie and I met earlier today (Wednesday) to score the competitors on every aspect of their trips. See the scores below…
Destination WOW
| Category | Stephen | Nick | Scoring rule and notes |
|---|---|---|---|
| Location | 2 | 2 | Did this traveler find a way to use points to position themselves in particularly scenic, awesome, and ideally located accommodations? (3 possible points) |
| Adventure | 2 | 6 | Did this traveler include an activity that was exciting or pushed them outside of their comfort zone? (3 possible points). Nick’s trip was so full of adventure that we doubled the top score in this category. |
| Relaxation | 3 (Beer Spa!) | 1 | Did this traveler take advantage of the luxury side of points and miles in a way that helped them relax? (3 possible points) |
| Food | 1 | 1 | Did this traveler find a way to engage with the local cuisine in an interesting way? (3 possible points) |
| Local Exposure | 2 | 2 | Did this traveler include activities that gave them a glimpse into the local culture of their destination? This could be anything from cooking classes to chit chats with locals. (Or something we haven’t even thought of yet!) (3 possible points) |
| Out-of-the-Box Ideas | 2 | 2 | Did this traveler do something that surprised us, and maybe gave us a good idea for our own future travels? (3 possible points) |
| Destination Total | 12 | 15 |
Applicability
| Category | Stephen | Nick | Scoring rule and notes |
|---|---|---|---|
| Replicability | 3 | 0 | Is the traveler’s use of points reasonably repeatable by others? (9 possible points). Nick’s trick wasn’t as replicable as Greg’s due to taking advantage of a short-term Iberia deal |
| Applicability | 6 | 6 | Is the traveler’s use of points applicable to most of our audience? (e.g. do you have to have a specific card to make it work? Do you need elite status? Do you need to start from a specific location? Do you need to be able to travel without luggage? These would detract from applicability.) (9 possible points). Both trips were more generally applicable than Greg’s (Greg took more advantage of elite status, and friend connections) |
| Applicability Total | 9 | 6 |
Value
| Category | Stephen | Nick | Scoring rule and notes |
|---|---|---|---|
| Dollar value | 3 | 0 | How much would this trip have cost if booked with cash? (The traveler will earn as follows: Less valuable than Greg’s trip by >$300 = 0 points, at least within $300 of Greg’s value = 3 points, $300+ more valuable than Greg’s trip = 6 points.) |
| Frugality | 2 | 2 | Once we factor in the value of rebates, points earned, etc, what was the NET cost for the whole trip? The lower the better. (Scoring for this metric will go as follows: The traveler spent more than Greg = 0, the traveler spent within $100 of Greg = 2 points, the traveler spent less than Greg = 4 points, the traveler spent less than everyone = 6 points). |
| Pro Behavior | 2 | 2 | Did this traveler highlight any tricks of the miles and points trade that go a level deeper than simply redeeming the first award found? (But remember, even pro tricks should maintain the primary standard of replicability.) (6 possible points) |
| Value Total | 7 | 4 |
Extras
| Category | Stephen | Nick | Scoring rule and notes |
|---|---|---|---|
| Budget | Passed | Passed | Did the traveler stay within the 100K / $1K budget? (Traveler will score 0 points for passing and -10 for failing.) |
| Proper Lodging for 3 nights | 10 | 10 | Did the traveler spend at least 3 nights in proper lodging (with a bed, etc)? (This will be scored as follows: Fewer than 3 nights = -10 points, 3 nights = 0 points, 4 nights = 5 points, 5 nights = 10 points, 6 nights = 15 points) |
| Check-in attendance | 3 | 3 | Did the traveler make it to all of the live check-ins (or at least within a 10-minute grace period)? (Traveler will receive 1 point for each check-in attended, and -3 points for each check-in missed.) |
| Daily post updates | 6 | 6 | Did the traveler successfully write at least one journal update for each day of their travel? (Traveler will receive 6 points for total success, 3 points for missing just one day, and -6 points for missing more than one day.) |
| Secret Destination Points | 4 (Czech Republic) | 4 (Serbia) | Did this traveler end up in one of the secret destinations Carrie pre-determined as being extra bonus-point-worthy? [Did they go to a country that has not previously been featured in a Frequent Miler challenge? (4 bonus points for this one.) |
| Extras Total | 23 | 23 |
Style
| Category | Stephen | Nick | Scoring rule and notes |
|---|---|---|---|
| Luxury flights | 0 | 0 | Were the flights comfortable and luxurious? (6 possible points). Both flew economy — not as luxurious as Greg’s flights. |
| Luxury accommodations | 4 | 4 | Was the lodging comfortable and luxurious? (6 possible points). Both featured hotels that were slightly more luxurious than Greg’s |
| Lounges, massages, etc | 2 | 2 | Were there other luxury experiences (lounges, massages, etc.) that were made possible thanks to a good use of points & miles? (6 possible points). Both used lounges, about the same as Greg |
| Style Total | 6 | 6 |
Grand Total
| Stephen | Nick | Notes | |
|---|---|---|---|
| Grand Total | 57 | 54 | Congratulations Stephen! |
And the winner is…
Based on the scores presented above, Stephen wins Frequent Miler’s 2025 Team Challenge! Congratulations Stephen!
Vote
Your turn… who do you think had the best vacation?
We recognize that our audience doesn’t always agree with the way we judge these competitions. That’s fine! With our audience choice vote, you can select who you think truly deserves to win. Since I’m not judging this vote, my name is in the mix too. Want to convince others to vote your way? Please comment below!
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stephens was basic, where nick’s was not
I believe Nick should get more points for location. Steven’s locations are usual highly touristed locations – London, Munich, and Prague. Whereas Nick’s locations are relatively less popular/known.
And I felt getting a local person to spend whole day with him, showing him around etc was more local exposure for Nick.
I guess that in the spirit of best uses of points, Steven should win, because he was able to book flights for two people instead of one. However, most of the scoring of the challenge seemed to me to be about planning and executing the vacation rather than simply using points, and I don’t think Nick gets nearly enough credit for his vacation.
I suppose it may be unfair to punish such a consistent theme, but Stephen’s vacation was basically just drinking huge quantities of beer. He seems to really love beer, so that’s fantastic for him, but it doesn’t seem to me to have the same imagination as Nick. If nothing else, I am very worried everyone is skipping past an element of Nick’s adventure that he downplayed: running out of money and turning $100 into $200 to enter the tournament. It’s a remarkable act of sang-froid in any case, but coming on the heels of Casino Royale, it’s too cool for words.
Three fantastic trips – congrats all and thank you all five of you for planning and executing this challenge! I had a lot of fun following along and it’s definitely given me some ideas for my future trips (hoping to make Prague happen in December).
I thought the scoring scheme was reasonable when announced, but when it happened on the livestream, it felt unsatisfying and somewhat artificial. By that, I mean that the contestants did some really cool stuff or really creative things or showcased some clever uses of points but the scoring system didn’t really highlight that. And it felt artificial because they were being compared with somewhat arbitrary targets, like within $100 of Greg (which they couldn’t necessarily aim for because they didn’t know that exact number until they were about to start their trip). That said, coming up with a fair, interesting, sensible scoring system is hard, and not the main objective of the challenge, so as long as the contestants know what the scoring system is in advance, it’s all good.
While all three trips had great aspects of the game we play, one thing stood out to me. Greg spent about 3/4 of his points on flights, Nick about 4/5 on hotels, while Stephen was more balanced on flights vs hotels. To me at least, that gave Stephen’s trip a more balanced feel and really showed the “value” of points, especially if you’re on a budget.
Well put. I don’t know how anyone can be declared a winner for this challenge that was just too open ended, and I absolutely hated the comparisons to Greg’s trip as the “benchmark”. I would have personally thoroughly enjoyed both Stephen and Nick’s trips, but I didn’t see much from Malta that makes me want to go visit. I am happy with either Nick or Stephen winning this challenge but to me it should be a tie.
BTW, when will Greg share how much he spent to bring 4 other people along for his trip?
Well, in addition to scoring being hard, it’s also subjective, as the multitude of opinions show… You didn’t like Malta, but I thought it was great and would love to visit. We’re probably all focusing too much on the scoring, myself included haha. I don’t see the relevance of the cost of Greg’s guests though.
Stephen should have gotten an extra point under “out of box” ideas for bringing two people along instead of one. I can’t think of anything more out of box compared to what we were all expecting than being able to include an entire extra person (points only), and that surprise doesn’t seem to be accounted for very well elsewhere in the judging.
I also think that Stephen is missing some points in the Food and Local Exposure categories. After all, he went to OKTOBERFEST in GERMANY. I’m not sure how much closer you can get to food and local exposure than either of those two together. There was also a good write up about dishes at a local Czech restaurant!
Hope Tim and family are doing alright. He was off to a strong start. The suite he found in London was the diamond in the rough of the contest.
I’m voting for Stephen since he was able to use his allotment of points to cover both he and his wife through the trip and landed well under budget! This was great and showed that a couple could travel to interesting destinations using 100K points and $1000 and could attain these amount of points with 1-2 credit card SUBS! Thank you Stephen for proving this out!!!
How much are Nick and Stephen paying for votes?
Value Stephen wins but Nick’s trip was much much more interesting.
Unfortunately as a competition I didn’t enjoy this one as much as past iterations. Part of that was due to Tim’s unfortunate circumstances – hoping for the best for him and his family – but the rule-bending, funny math and the benchmark structure were the bigger factors. Looking at them solely as trips, however, each one seemed very enjoyable. I could see myself or others easily replicating them. In the end, I voted for Stephen because he showed that you can design a wonderful trip for two and fit it within a budget, even if the cash portion of that budget was a little squishy :). Also, I’m a big beer fan :). But kudos to Nick too. I really want to visit Andulacia one of these days, but I wasn’t aware of the Caminito del Rey, so now I’ve got another reason to get there sooner rather than later.
I think Stephen’s trip was the more appealing one and it felt like Nick was barely scraping by most of the time due to budget limitations. I mean, getting bakery leftovers for two meals? Using priority pass to cover multiple meals? I think Nick had one, maybe two good meals during the entirety of his trip. Not exactly what I have in mind when I think of a vacation.
Tons of fun and hope Tim’s doing alright with fam. I think they were neck and neck, and Stephen’s better half was the decider!
For future contests I’d suggest more granular scoring…instead of 0/3/6 pts for like $100/$300 or whatever, why not put some middle ground in between – I think this would make it easier to differentiate.
I also would take away points for any major vacation without a hugely memorable, excellent meal – I would take points away from family and friends, not just the FM team! This is where Greg knocked it out and Stephen & Nick phoned it in.
Great fun team!
Nick had an interesting meal in Belgrade featuring a sabre.
100% valid point, that was very cool! They still both earned 1 of 3 possible points from Greg & Carrie, so I still think they can do much more – these are professionals! 🙂
Bravo Stephen and Shea. Really enjoyed this challenge, such fun to see what everyone did and how far 100k can take you. I have zero interest in beer or poker but it showed how you can build a trip to follow your interests. I even enjoyed your torturously geeky and convoluted scoring on the live stream!!! There are so many bland, identikit points bloggers but you all have so much heart. This site is fun because you’re about personality, entertainment AND all the best thoughtful assessments about maximizing mileage in both accumulating and spending points. Well done everyone – looking forward to hearing what Tim would have done too.