Frequent Miler’s 100K Vacay challenge is starting soon! We’ll kick off the official challenge on October 1st, but my part starts a week earlier. On Thursday, September 25th, I’ll head out on my “setting the bar” vacation, where I’ll spend no more than 100,000 Chase Ultimate Rewards points and $1,000 cash. While the details of my trip will be revealed as I go, in this post, I’ll cover my vacation planning strategy…
What is the 100K Vacay challenge?
This fall, Nick, Stephen, and Tim have 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. In the end, we’ll find out who can book the most amazing 100K point vacation!
Repeatability over perfection
This is a weird challenge for me since I’m not in it to win it. I’m a judge in this competition, and the purpose of my trip is to set a bar against which the challengers (Tim, Stephen, Nick) will be judged. Instead of getting overly creative, my approach was to use the strengths of Chase Ultimate Rewards points straight up. And rather than seeking out the most fantastic possible trip that can only be booked when the stars align on the fourth Thursday of the month, I leaned towards easily repeatable booking options. For example, before Virgin Atlantic increased its award surcharges, it was sometimes possible to book Virgin Atlantic flights to London, in business class, for as few as 29,000 points and a few hundred dollars in fees. Those opportunities, though, were few and far between. While I was tempted to hunt down one of those award flights, I knew that it would make my trip less broadly applicable.
Hyatt hotels
I was assigned Chase Ultimate Rewards points for the benchmark trip for a reason. This challenge requires staying at least three nights in a hotel, and Chase is the only program in the competition whose points transfer to Hyatt. And Hyatt is the only major hotel program that consistently offers great value for its points. With that in mind, I looked only to Hyatt’s portfolio for my hotel bookings.
Book a “real” vacation
A goal I set for myself was to design a vacation that I would really consider booking outside of a team challenge. This led to several constraints based on my travel preferences:
- The destination must be interesting. Sure, I enjoy drinking a Mai Tai on the beach, but I really enjoy discovering new places, interacting with people, and trying out new-to-me cuisines.
- Long flights should be comfortable. For overnight flights, I want a lie-flat seat. For daytime flights over 5 hours long, I want premium economy or regional first-class seats.
- Flight connections should be minimized. For a regional destination, I want a non-stop flight. For a major international destination, I want no more than one stop. And for remote international destinations, I want no more than two stops.
Get great value for my points
With Chase Ultimate Rewards points and a Sapphire Reserve card, it’s possible to get up to 2 cents per point value when booking Points Boosted premium flights and hotel stays through Chase Travel℠ (see: Evaluating Chase’s new Points Boosts). My goal was to show that you can get far better value by strategically transferring your points to airline and hotel partners.
Have fun
My final trip objective is to have fun. I’m excited about the trip I booked! Even better, I have a few surprises set up that should prove fun for me and for everyone following along. I can’t wait!
Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
Just curious about the competition design. Why have Greg do a trip himself, but not have it be part of the competition?
I assume because they needed to show what is possible with each of the 4 main transferrable currencies and if he was not a competitor that would leave Carrie on her own to judge (which I wouldn’t have an issue with personally). I also question the comp design but appreciate the entertainment value.
*if he was a competitor
“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.”
They all think whoever got Chase points will win the competition. So instead of having it as part of the competition, they use it as the standard for the three competitors to chase after. If one competitor somehow manages to beat Greg’s trip, he will be in a great position to win this challenge.
It’s due to a number of things:
Greg for the benefit of us can you please clarify if this is allowable for purpose of the challenge, and if yes if they will be considered as deduction of points or cash.
1) use of free night certificates
2) use of Citi $100 hotel travel portal credit
3) use of $300 capital one travel portal
4) any other credits that are not transfer bonus to partners
Not certain, but I believe that airfare and hotels have to be paid entirely with the 100,000 transferrable points chosen by each competitor. That would exclude all the items mentioned above. The cash would just be for airfare co-pays and all the other activities that should turn the trip into a vacation.
None of those are allowed
If this were a court case you would be ethically required to step aside from judging due to a conflict of interest (setting the bar and then judging against that bar) but you’re the Frequentmiler and its all for fun so let the games begin!
In case it wasn’t clear, the contestants are competing against each other, not with me. My trip gives the judges (me and Carrie) a comparison point, which will help us score the other trips.
“My trip gives the judges (me and Carrie) a comparison point, which will help us score the other trips.” My point exactly! You are comparing their trips against your own trip but let not your heart be troubled. The main thing here is the entertainment value and the opportunity to show off what can be done with each of the 4 main transferrable currencies. Looking forward to the competition!