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Frequent Miler's 100K Vacay

Challenge Announcement (Post)
Challenge Announcement (Podcast)

Greg has planned a trip he thinks will showcase just how powerful 100K Chase Ultimate Rewards points can be for building an incredible vacay.

But Greg's not the only cowboy in town and Chase isn't the only resource out there for transferable points. Once Greg's "benchmark trip" is finished, Nick, Stephen, and Tim have each picked a different transferable points currency they think can compete with Greg’s Chase-fueled 100K Vacay. Nick will use American Express Membership Rewards points, Stephen will use Capital One Miles, and Tim will use Citi ThankYou points. In the end, we’ll need your help deciding if anyone's 100K Vacay beat Greg's.

Can anyone beat Greg and his 100K Chase Ultimate Rewards points?

First...

Greg will set the bar with a "benchmark trip" using 100K Chase Ultimate Rewards points. His will be the trip to beat.

Then...

Nick, Stephen, and Tim will try to out-shine Greg (and each other) using 100K of the points they think will compete the best.

Greg's 100K Vacay (The Benchmark Trip)

100K Chase Ultimate Rewards Points

$1,000

September 25-30

Greg The Frequent Miler
Greg The Frequent Miler
Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.

Greg's benchmark trip journal

My 100K Vacay bar-setting strategy (Greg’s Journal)

Featured ArticleGreg The Frequent Miler - 14
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....
Read more

Nick's 100K Vacay

100K American Express Membership Rewards Points

$1,000

October 1-8

Nick Reyes
Nick Reyes
Nick Reyes is a (fairly) regular guy with an animalistic passion for maximizing the value of miles and money to travel the world in comfort and style. There is little in life that he loves more than finding a fantastic deal and helping you shop smarter & harder to achieve your travel dreams.

Nick's trip journal

Why Nick chose Amex points for 100K Vacay

Award BookingNick Reyes - 8
With Greg "setting the bar" for our latest Frequent Miler team challenge by using Chase Ultimate Rewards points, you might wonder why I chose...
Read more

Stephen's 100K Vacay

100K Capital One Miles

$1,000

October 1-8

Stephen Pepper
Stephen Pepper
Stephen Pepper spent 7 years traveling around the US on a 50 state road trip with his wife Shae and their dog Truffles. Finding opportunities to earn miles and points was one of the ways they could afford to do that, so he'll try to help you do the same for your own travels.

Stephen's trip journal

Why Stephen chose Capital One Miles for 100K Vacay

Featured ArticleStephen Pepper - 26
Our 100K Vacay challenge is coming up this fall, so it's time to share why I chose Capital One miles for it as my...
Read more

Tim's 100K Vacay

100K Citi ThankYou Points

$1,000

October 1-8

Tim Steinke
Tim Steinke
My wife Erin and my first big journey together went around the world in 100 days for our honeymoon, a trip in which I had one car accident and got one speeding ticket in every country that we visited (I think that I may still have an arrest warrant in New Zealand for an unpaid ticket, but we’ll keep that between us). We currently live in Washington State; we own a winery, ski after work and hike as much as our elderly knees will let us.

Tim's trip journal

My 100K Vacay Strata-gy with Citi ThankYou Points (Tim’s Journal)

Featured ArticleTim Steinke - 21
It's September 1st, which means we're one month to the day from the beginning of the 2025 Frequent Miler Annual Challenge. This year, we're...
Read more

Judges

Greg The Frequent Miler
Greg The Frequent Miler
Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.
Caroline Yoder
Caroline Yoder
Carrie Yoder spent ~5 years as a digital nomad with her husband Drew managing their points and miles travel blog, "Travel Is Free". Now she uses the content management, digital media, and design skills she learned then with Frequent Miler.

Judging criteria...

Greg and Carrie will judge the three travelers, focusing on the following primary qualities:

  1. How stylish is this vacay?

  2. How affordable is this vacay?

  3. How well does this vacay leverage the unique aspects of this contestant's transferable points currency?

  4. How broadly applicable is this vacay? (Would it be reasonably replicable by one of our readers?)
Our judges will also award some surprise bonus points for mini-challenges that will be revealed later. You can read more about the rules, dates, and judging criteria in this post below:

Announcing the 100K Vacay team Challenge! [Mark your calendar]

Featured ArticleGreg The Frequent Miler - 72
The Frequent Miler team is readying for our next challenge! This year, we'll compete to see who can book the most amazing 100,000-point vacation. This...
Read more

Airline Resources

Hotel Resources

Award Booking Resources

Points and Miles Resources

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