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.
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 | 3 | 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?
[UPDATE: The audience choice voting is closed. Results can be viewed below]
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!
Which 100K Vacay trip was really the best?
- Stephen and Shae's 3-country beer crawl (52%, 319 Votes)
- Nick's James Bond themed adventure (30%, 186 Votes)
- Greg's Malta vacation (18%, 114 Votes)
Total Voters: 619
Loading ...
Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
Tim’s trip looks amazing. It is very impressive that all three trips were so strong and so completely different.
I was disappointed that Tim had to drop out because I think his trip would have been very competitive if completed like he had outlined.
I think Tim’s trip would’ve been the relatively easy winner. That’s definitely the one I would have most enjoyed and the value he got was incredible.
I just read Tim’s trip journal and wanted to comment but it seems the post is locked down. I really liked his itinerary and out of the 4 trips, it would be the one I would try to book something similar. I was checking Flying Blue for OSL-NYC (and vice versa) trips and could not find anything close to his redemption costs in both points and taxes(either in E or E+). Did he book during a promo time or did FB revamp their tax and fees?
I don’t have accounts with either but Etihad and Singapore are also SK partners.
Thanks but Tim’s post said “ I found the perfect option: SAS Premium Economy from Oslo to Newark, booked using Flying Blue Miles”.
I see the comments to his post is open again so I am going to put a comment there now.
Ah I missed that – there was a 20% transfer bonus to Flying Blue during the planning period but I also was not able to find anything with SAS PY on Flying Blue that low
I missed the fan vote, but I would have voted for Greg’s trip b/c it seemed the most relaxing; therefore most similar to what I would want to replicate.
Having said that, I enjoyed all of them! Nick’s desire to do “things he’s always wanted to do” is admirable (even if not on my bucket list!) & Stephen’s epic suite in Prague were both super awesome!
Keep it up, FM!
Destination WOW, Nick got 14 (2,6,1,1,2,2) not 15.
Great catch. We had meant to give Nick 3 points for the Out of the Box sub-category. I’ve fixed that.
I really enjoyed following all three trips! I think Greg’s is the one I would most like to replicate, Nick’s is definitely the one my husband would most like to replicate and Stephen/Shae’s is what I would pick if traveling as a couple. Really great job everyone!
Greg’s trip totally had a theme! Reunions? Getting the band back together?
Let me caveat my comment by admitting this is silly and I read the post anyway.
With that said, why was the headline to this post “Stephen wins 100k Vacay”? Could’ve held out a little suspense for those of us following along!
In all sincerity, enjoyed the content as usual. Now let me return to my viewing of The Sixth Sense (Haley Joel Osment sees dead people!)
Same! I hadn’t had a chance to watch the youtube video announcing him as winner before I saw the notification for this post. 🙁
Is there a place to see Stephen’s ccp value for lodging and airfare only, like Greg and Nick did in their posts? I find this breakdown much more useful than an overall trip cost – it’d be helpful to see the value of Capital one points relative to the other transferable currencies as it pertains to flights and lodging specifically.
I enjoyed following this year’s challenge as usual. Thank you for giving us great entertainment and tricks that are easy to replicate. Only time I reinstall instagram and log in using my P2’s account to watch your daily updates. I was very curious to know what Nick is doing in the whole time every day than Stephen and he didn’t disappoint me at all. Thank you Nick.
One thing i didn’t see mentioned in the comments so far is that Shae doesn’t particularly like beer. So, on one hand, she showed what could be an alternative in London; but on the other hand partook w/ Stephen in the two other locations. That’s dedication and true love!
While I understand the challenge entailed doing a lot of stuff with limited points and budget, one of my goals when I travel is not to wear myself out so I come home sick. Perhaps being healthy when finishing the trip should be worth bonus points, or, conversely, points subtracted for being ill.
I also agree with some other writers that having a partner while traveling helps ease the way, which may have influenced points accrual.
One issue with these competitions is that, since they’re essentially work, the competitors have to squeeze a lot in to an unreasonably short amount of time. I’d like to see separate write-ups of “What my trip would have looked like in real life” where they extend it to a “reasonable” number of days. So Nick and Greg surely would have had at least one inexpensive beach day added into their trips, Nick probably would have stayed in Belgrade a few extra days, and gone to Plovdiv from Sofia, and so on.
Also, since it’s a “work” trip, there’s a lot of extra stuff that the competitors have to do — collecting, editing, and transmitting video, updating their posts, doing a live stream — that a “normal” person wouldn’t have had to shoehorn in, often at the expense of sleep.
Honestly, I wore myself out with the London day and then we spent so much time around the public. I *may* have still gotten sick but with only 3 hours of sleep (after 5 non stop days with my parents in NYC) and then 10+ hours mostly walking in the rain around London to jump straight into a long travel day etc etc etc. I can totally see why I got sick. I’m not very happy about it either and I should probably get docked all the points LoL.
One of my goals is to avoid spending a ton of time on transportation that is needed to cram in multiple destinations into a short trip. Really the only relaxing vacation was Greg’s, because he was not in it to win it. This is the only trip that was easily replicable by the rest of us for the points/cash allowed because he could stay in place.
Agreed, we’re the same. The other trips were almost like a sampling of what you could do in theory, but realistically anyone would add nights in most stops… although even with more days added in, we also personally favor not losing much time to changing destinations. Greg’s was definitely the most relatable trip for our family, regardless of the points, because we tend to not hop around.
I like beer but come on. The whole trip was sleeping and drinking free beer and eating horrid looking food!
Thank you! I completely agree! I’ve been to Octoberfest in Munich, and it is definitely fun. The rest of the trip was sleeping until between 10AM and 2PM, realizing they couldn’t do what they wanted to do and returning to the hotel for more sleep, eating like an unsupervised teenager including vending machine meat, and drinking beer. Seriously? Is it any wonder they got sick?
The vending machine meats and double dumplings made my stomach hurt.
I have not been to Octoberfest. Would like to. I have been to Prague and can’t imagine not going to castle hill or the Kafka museum or actually seeing the clock do its thing.
And I would be drinking beer the entire time…in addition to those things. And I’d be with my wife who doesn’t like beer and who wouldn’t be bathing in beer.
Don’t get me wrong. Good job Stephen. You had fun. Shae had fun.
My issue is with the scoring.
And who cares how it compares to Greg’s trip. Not me.
Fun reading and watching it all though.
Just the wrong winner.
Apologies. One more. Who has ever said “I’m really stressed and need to relax. I’d like to climb into a tub of beer and let the world melt away.”? No one. Ever. Why not a tub of cola? Coffee?
Been to Prague thrice. Thrice passed on soaking my entire body in a non water substance. That score is the difference in the completion on its own!
And yet there seem to be for-profit businesses offering this service in several cities in Europe.
judgy and condescending much?
Rarely, and certainly not this time. Thanks for asking though.
I have been chided for judging the activities folks chose to do and I think that’s fair…because we all like different vacation activities. But the thing is, each competitor found a way to get to Europe and back and visit a couple of countries, and do things they like on 100,000 points and $1,000. However, only one of them also brought along another person using the same ponts budget to provide their hotels and flights .,.. in my book, they win.
That wasn’t part of the contest guidelines. Jo credit should be given. Plain and simple.
Nick did a great job chasing down personal goals. I just think that Stephen did things that resonated more with me.
Honestly loved the Peppers’ trip! It was definitely the one most relatable to me (economy travel, decent hotels, and lots of fun exploring while still relaxing.) However, they should’ve taken the train instead of the bus! Missed opportunity!
I agree that they probably should have taken the train, but I really liked the bus for the blog. The bus isn’t something covered in points/award travel blogs very often and it showed a very economical option when that is needed. And that the time was about the same as plane is just bonus!
Why? Same time, same locations, half the price.
Personally, i prefer the more room and the ability to stand / move around on long trips that trains provide; but that doesn’t matter to a lot of people.
The last time I did this, the “train” included a DB double-decker van drive between Prague and Nurnberg. Only the Nurnberg-Munich leg was actually on a train. The bus seems fine in this case.