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Frequent Miler's 100K Vacay

Challenge Announcement (Post)
Challenge Announcement (Podcast)

Greg planned a trip he knew would 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. Nick, Stephen, and Tim each picked a different transferable points currency they thought could compete. Nick selected American Express Membership Rewards points, Stephen selected Capital One Miles, and Tim picked Citi ThankYou points. Unfortunately Tim's trip came to an early end due to an unavoidable need back home, so it was up to Nick and Stephen to see this challenge through.

In the end, Stephen's creative use of Capital One Miles to affordably stay in Munich for Oktoberfest as well as his ability to bring his wife along within his 100K points budget gave him the win! Congratulations Stephen (and Shae) for winning the 100K Vacay Challenge!

First...

Greg set the bar with his "benchmark trip" using 100K Chase Ultimate Rewards points. His is the trip to beat.

Second...

Nick and Stephen tried to out-shine Greg (and each other) using 100K of the points they thought could compete the best.

YouTube live check ins and recaps...

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 Final Score Card

Greg's benchmark trip to Malta

Greg spent just 97K Chase Ultimate Rewards points and $968 for an epic vacation in Malta. He spent 4 nights in comfort at the Hyatt Centric Malta, learned about Malta’s fascinating history, sampled local delicacies, and snorkeled along the rocky coast. Can the others beat this trip?

For the full story, read his trip journal below.

Grading myself: B+ (Greg’s 100K Vacay Journal)

Featured ArticleGreg The Frequent Miler - 164
My trip is done. I'm safely back in Ann Arbor, reflecting on my wonderful trip. For the most part, things went great. Malta proved...
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 winning trip to London, Munich for Oktoberfest, and Prague

Final budget status_ Stephen
This was Stephen's final budget status

Under points & under budget (Stephen’s 100K Vacay journal)

Featured ArticleStephen Pepper - 188
My 100K Vacay has come to an end and even I'm impressed by the numbers I put up (or, more like, didn't put up!) Want...
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 bond-like trip to Spain, Serbia, and finally to Sofia, Bulgaria for the Vamos Poker Tour

Final budget status_ Nick
This was Nick's final budget status

Shipping back to Boston & a final cost tally (Nick’s 100K Vacay journal)

Award BookingNick Reyes - 161
I am publishing this post from 36,000 feet to share a full tally of the final costs from my 100K Vacay. Read on for...
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

This was Tim's budget status as of his early return on October 2nd
This was Tim's budget status as of his early return on October 2nd

7 nights in London and Norway for 100,000 points: Mountains, fjords and ferries (Tim’s 100K Vacay Journal)

Featured ArticleTim Steinke - 75
Congrats to Stephen Pepper, who deservedly won the 2025 Frequent Miler Annual Challenge, 100K Vacay! The goal this year was for us to compete...
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 judged our travelers, focusing on the following primary qualities:

  1. Destination WOW

  2. Applicability

  3. Value

  4. Extras (like staying in budget)

  5. Style
Our judges used each of these primary categories to create more granular subcategories.

Stephen won 100K Vacay! [Update: Congrats to Stephen for winning the audience choice vote too!]

Award BookingGreg The Frequent Miler - 115
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...
Read more
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