Those who have been following the 100K Vacay challenge this week know that Greg’s been designing an excellent vacation in Malta to serve as the benchmark trip, which will set the bar for the rest of our annual challenge competitors.
Armed with 100K Chase Ultimate Rewards points (arguably the most powerful transferable points program for a comfortable luxury vacation), Greg had some unique advantages the other competitors won’t have – most notably, an ability to transfer to Hyatt for luxury lodging at a reasonable price in points. This put him in a good position to set the bar for a vacation the others will have to try to match (or even beat!).
What is the 100K Vacay challenge?
Nick, Stephen, and Tim each picked a different transferable points currency they think can compete with Greg’s 100K Chase Ultimate Rewards points, each trying to beat Greg’s 100K Vacay with one of their own. Unfortunately Tim's trip came to an early end due to an unavoidable need back home, so it's up to Nick and Stephen to see this challenge through.Since Greg’s trip is setting the standard, we’ll go through each metric in our scoring rubric and describe the bar Greg set for each. (There are some metrics where he set a higher bar than others so our competitors – Nick, Stephen, and Tim – will have a healthy but achievable challenge in front of them!)
How we’ll be judging the 100K Vacay challenge
Greg and I will be the official judges of this challenge, comparing Nick, Stephen, and Tim’s trips to Greg’s benchmark trip, awarding points based on the following primary standards. (Of course, we love acronyms, so here are the general targets we’ll be assessing to see how each competitor is making WAVES in the competition. )
- WOW (Destination wow!)
- Applicability
- Value for your specific points
- Extra bonuses (outlined later in this post)
- Style
Using these primary goals as guideposts, we’ll decide which competitor had the best 100K Vacay.
More details can be found here: How we’ll be judging the 100K Vacay challenge.
How Greg set the benchmark

Destination WOW! (18 possible points)

- Location location location (3 possible points)
As a destination, Malta had everything you might want in a vacation: beaches, rich historical sites, and an interesting cultural flavor. However, the hotel he selected in Malta (Hyatt Centric Malta) was not necessarily a prime location unless you’re interested in nightlife, restaurants, shopping malls, etc. There were some worthy attractions within walking distance of the hotel (like St. George’s Bay), but every day Greg and his crew took some form of transportation – bus or rideshare.) - Adventure (3 possible points)
Greg spent the better part of a day snorkeling in an off-the-beaten-path cove, then hiking along the rocky coast.

- Relaxation (3 possible points)
What followers may not know is that Greg had a healthy amount of downtime each day. (The first day was the only day without a few hours of rest in the afternoon.) Otherwise, Greg had no specific activities dedicated to relaxation. - Food (3 possible points)
Greg had a food-focused activity almost every day of his trip (3 of the 4 days). First, he invited his old couch-surfing connection from 40K to Far Away to reprise the sunrise picnic he’d created in Johannesburg, South Africa, 6 years before, this time with a sunset beach picnic instead. The picnic focused on local dishes (curated by chef Bjarne). Next, he sampled the most famous Maltese pastry (pastizzi) at the pastizzi shop most recommended by the tour guide of the free walking tour he participated in. And finally, he splashed out on the final night with a (very affordable) 7-course tasting menu at a traditional restaurant selected by the same Culinary Concierge he’d traveled with a few years ago in 3 Cards 3 Continents. By the time he left, he had sampled many local dishes at very reasonable expense.

- Local exposure (3 possible points)
Greg shuffled his original plans in part to forego a touristy kayak activity, which would have hit all the tourist hot spots. Instead, he opted for snorkeling at a local spot he’d learned of from a blog. True to its description, this spot had no crowds at all, and many of the other swimmers did indeed seem to be locals. In addition to this, Greg took not one, but two free tours with a local Maltese tour guide – one in Valletta and the other in Mdina. He also made use of a local bus, which gave him the opportunity to chat with a local who shared interesting insights about modern Maltese life. (This did not make it onto Instagram sadly, because, well, believe it or not, we don’t actually film everything.) - Out-of-the-box ideas (3 possible points)
One of Greg’s more out-of-the-box ideas was his least glamorous but perhaps most clever flight booking. To avoid the painfully high ($500) fees on a Virgin Atlantic flight home from LHR to JFK for 10.5K points, he instead booked an AMS > LHR > JFK flight for 14.5K and half the fees. (And because of a transfer bonus, he only needed 12K Chase Ultimate Rewards points for those 14.5K Virgin Atlantic miles.) His decision to create a local-food picnic was an out-of-the-box idea worth repeating as well.
Applicability (18 possible points)

- Replicability (9 possible points)
Greg was very intentional about using his true home airport as his starting point (Detroit), even though we are technically allowing our competitors to pick their starting point. He did this specifically to ensure his trip would realistically represent what a reader might be able to do (even our readers who don’t live in major hubs like NYC.) Greg also used Air Canada Aeroplan miles for his flight from JFK to Malta because, even though there are programs he could have used to get better value on business-class flights to Europe, they’re far more difficult to find. - Applicability (9 possible points)
Greg’s flights and hotels could all have been booked by anyone with 100K Chase Ultimate Rewards, making it extremely applicable. He did, however, use the professional (paid) version of Award Tool to find his award flight and applied a Hyatt Suite Upgrade award (which not everyone would necessarily have). He also took advantage of his Globalist status for free breakfast and lounge access (which he used as his dinner for at least one meal). His applicability was very good, but not perfect – our competitors should be able to beat him at this metric if they want to.
Value (18 possible points)

- Dollar value (6 possible points)
This vacation would have cost $4,341 to replicate without miles and points. (This includes everything.) - Frugality (6 possible points)
Greg’s net cost was $968. - Pro behavior (6 possible points)
Again, Greg’s Virgin Atlantic flight home was positioned from Amsterdam specifically to minimize high fees from London (despite transiting through London). This could be considered a pro tactic.
Extras (28 possible points)

- Budget (0 possible points)
Yes, Greg stayed within budget! He had 3K points and $32 left in his budget. - Proper lodging for 3 nights (15 possible points)
Greg spent 4 nights in a real bed. Our competitors can potentially earn more points if they spend more nights in a real bed than he did, though they’re only required to spend 3. - Check-in attendance (3 possible points)
This metric does not apply to Greg since he did not have any live check-ins throughout his trip. - Daily journal updates (6 possible points)
Greg managed to publish a journal update every day of his trip. - Secret destination points (4 possible points)
Greg did end up in one of the pre-established secret destinations. (How these secret destinations are established won’t be revealed until the end.)
Style (18 possible points)

- Luxury flights (6 possible points)
Greg’s longest international flight (Air Serbia Business class) offered a lie-flat bed, a pre-selected meal, and most other standard business-class amenities. He noted that not all seats seemed equivalent, but he selected one with the optimum amount of space, storage options, and aisle access. Greg’s second-longest flight (Virgin Atlantic premium economy) offered plenty of legroom, good seat recline, footrests, and excellent food and service. Greg also had 4 short economy segments. - Luxury accommodations (6 possible points)
The Hyatt Centric Malta is a Category 2 Hyatt. Greg used a suite upgrade for a balcony suite, and he also had club lounge access and free breakfast in the restaurant. - Other points-driven luxury (6 possible points)
Greg visited 5 airport lounges. On his outbound flights, he used Priority Pass to access the Lufthansa Star Alliance lounge in Detroit and the VIP One Lounge at JFK. Additionally, his Air Serbia business-class ticket gave him access to the Premiere Class lounge at JFK. On the return journey, Greg’s Delta Elite status gave him access to the KLM lounge in Amsterdam and the Virgin Atlantic clubhouse in London. Additionally, he was able to guest me into the VIP One Lounge at JFK with his Priority Pass, and to the KLM and Virgin Atlantic lounges with his status.
Wed, October 1st at 9pm ET: Challenge kick-off live stream
This Wednesday, October 1st, at 9 pm ET, instead of our usual Ask Us Anything Live, we’ll have our challenge kick-off, where we’ll make sure our contestants (and followers) are up to speed on how Greg’s trip set the benchmark. We’ll also check in to see where our travelers are, mentally and physically. Are they feeling confident? Did elements of Greg’s trip make them rethink their own? And have any of them already hit the road? Tune in to find out!
And of course, the best way to make sure you don’t miss these live episodes is to subscribe to our YouTube channel here and click the bell icon next to the “subscribe” button to enable notifications from our channel.

Don’t forget to follow our Instagram channel and read our contestants’ daily journals for the most current status of the ongoing 100K Vacay challenge!


![Stephen won 100K Vacay! [Update: Congrats to Stephen for winning the audience choice vote too!]](https://frequentmiler.com/wp-content/uploads/2025/10/100K-Vacay-winner-is-crowned-2-218x150.jpg)


It’s interesting to note that even with the expert points redemptions and frugal travel style exemplified by this trip, travel still isn’t “free” (sorry Carrie & Drew). This three-day vacation (three days on the ground, not counting travel on either end) cost $323 a day in cash, not counting any “acquisition costs” for the points.
Of course, in a “realer” scenario, where the trip is 10 or 14 days, the airfare co-pays and positioning flights would have been amortized across more days bringing the per-day cost down. On the other hand, I got the impression that Greg was definitely economizing a lot and missing some experiences he would have liked to have booked in order to keep things below budget, so that would have brought up the per day cash outlays.
I’m sure this isn’t a revelation to anyone, but I was surprised at just how much it costs to travel, even with points.
Very true, particularly for destinations in Europe and the USA. Took family to London and Rome this past summer versus Japan/other Asia and Spain last summer. I reckon it cost at least 2x more cash this past summer, despite far fewer flights. London is a must visit but nevertheless a one and done for my family.
Yes, agreed. I thought that I’d be able to do this for about $500 or $600 total, but multiple sub-$100 positioning flights and moderate Virgin award fees really add up! Also, I was surprised at how much the Bolt rides added up. Malta’s bus system isn’t fast and reliable enough to get around without major delays. There’s a huge cash advantage to staying either in a city that has great subways or a town that has everything you need/want in walking distance.
A plain list of the points and cash spent ( with redemptions) would be nice without having to dig for it. Or did I miss it somewhere?
It’s clearly listed in my journal post. I added a link to my journal at the top, but you can find it here: https://frequentmiler.com/100kvacay-greg/#Final_tally
Wait! You mean anyone . . . even a non-hobbyist . . . could have booked this trip . . . with points from a healthy sign-up bonus and a little bit of spending? You mean the FM team is not just about hair-on-fire types who are raking in millions of points per year?
I guess some readers who have commented as much were plain old wrong.
Excellent instructional exercise.
Thanks!
You guys should have the live up on YouTube already so people can use the notify feature. Also, Make Greg pay for stream yard also you’ve gotta stop with zoom. Thank you.
What’s wrong with Zoom?
Nothing at all. I think you’d find it easier for Carrie or whomever is leading to manage the questions on a service like streamyard.
It’s free and you are getting something out of it. Don’t complain.
Of course, as we know it is a monthly recurring thing, you could just set a recurring item with an alarm in your calendar app.
I’m not complaining at all. They could have significantly more viewers if they would just put up the live stream 10 to 24 hours before they go live so that everyone has the option to hit the notify me button on YouTube.
Streamyard or any other service would make it much easier for Carrie to lead the show.
Good day sir.
Yes, thanks. We plan to look into one of those services soon but haven’t had a chance yet. We tried Riverside (which can do the livestream stuff), but found that Zoom does such a better job at blocking out background noises that we went back to Zoom.
How can members get his chef for free?
Contact Bjarne on Couch Surfing like I did 6 years ago 🙂
Can you please share the name of the restaurant for the 7-course tasting menu at the traditional restaurant? Thanks!
Legligin
thanks!
Would’ve been more impressive without the magical Suite upgrade and free Globalist breakfast.
Maybe it’s just me, but using those perks seems to go against the spirit of this challenge.
If we’re going to call those out using Delta elite status for lounge access falls into the same category.
The whole focus of FM is earning points and status for cheap, so I don’t think it’s out of bounds – but I totally understand the opposing viewpoint that the average traveler won’t have access to these perks.
Yes, this was by design. Because I used my elite benefits (which detracted from my Applicability score), it makes it easier for the competitors to score highly on the Applicability of their trips (but it makes it harder to score highly on Style. Ideally, every competitor will beat my trip, but I wanted to set a high enough bar to make that difficult
I loved the Malta trip! I also agree with Sam. Using status for free food (breakfast and lounges) seems to violate the spirit of the challenge. If these perks were included using the allotted Chase points and/or cash, for example booking through The Edit, then that would easily be considered fair game. As it stands, the food budget seems nearly impossible.
The free room upgrade doesn’t matter, as long as the competition only has to beat the room that was actually booked using points. No one should have to turn down a free upgrade!
As for airport lounges, I suppose as long as the lounge was accessed using a card that was theoretically used to earn the points, for example the CSR, then that would also be reasonable. The competition would have the ability to use their Amex Platinum, Venture X, or Strata Elite lounge benefits in response.
I’ll wait and see how the “by design” portion works out. Hopefully I’ll change my mind!
Why? Greg barely mentioned the suite. As for breakfast, he actually had cash left in his budget to have eaten in a cafe.
Plus, part of the whole points and miles game is to achieve and exploit status for benefits, and it was explicitly allowed in this competition.
How difficult is it to “edit out” these very minor parts of the trip in your mind if you don’t pursue them?
Hi LarryInNYC!
I think the rules say using status is allowed, but detracts from applicability, yet Greg scored himself an ‘A’ in that category. Also note that without status Greg’s budget would’ve been blown. Greg reasonably gave himself a ‘C’ in the budget category, but perhaps it would’ve been an ‘F’ if he went over.
That doesn’t mean it wasn’t a great trip, or that we can’t “edit out” and take away some great ideas. We absolutely can.
I thought the essential idea behind the challenge was to showcase what could be done with 100K points and $1,000. The idea being that someone with those points and dollars would’ve been able to duplicate the vacation. Gary even notes that he could’ve ‘exploited’ better airfare, but it wouldn’t have be applicable to many people.
If you want to rub salt in his C1 wounds, dock a few points for not visiting the excellent capital one lounge at JFK.
Wrong terminal. And, the terminals are not connected on the air side.
Although you can visit 4 just for lounges if you have the time.
But I think Jeff’s point was teasing Greg because he can’t visit the C1 lounge since C1 doesn’t like him and won’t give him a card.
Greg put together a very interesting trip, for sure! Do we not get to know the actual scores for Greg’s trip though (how many points he got in each category)?
I was curious too. But Greg and Caroline are the judges.There’s a conflict of interest there if they rate Greg’s trip. Maybe it’s for us to think about.
My trip wasn’t supposed to be scored. It’s there so that we can assign scores to competitors on each aspect of their trips. They get more points if they complete an element better than I did and fewer points if they do worse.