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Frequent Miler Annual Team Challenges
Every year we try to design a team challenge that pushes us to the limits of our miles and points knowledge, and sometimes to the edges of our travel stamina.
Our goal is to showcase some of the most incredible (and even unbelievable) things you can do with miles and points. Most of these journeys aren't ones you'll want to replicate exactly, but we hope the ideas you'll gain as you follow along will be priceless for planning your own adventures. Maybe you won't fly last minute from LA to Morocco, but maybe you will visit Santa Claus in Roveniemi Finland.
Fall, 2025
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.
Fall, 2024
When SAS Eurobonus launched a promotion to earn one million miles by earning or redeeming SAS miles on flights taken with 15 different qualifying SkyTeam airlines by the end of 2024, we had to take the opportunity to make this our next team challenge.
We asked readers to submit tips, recommendations, and possible itineraries to help Greg, Nick, and Stephen satisfy the SAS challenge for 1M miles. Tim and Carrie judged which traveler met this challenge with the most "SAS" (speed, affordability, and style). But each traveler picked a follower whose tips helped them most. These helpers each won a prize, and a chance at the Grand Prize if their traveler won!
Spring, 2024
The Frequent Miler team's 2024 challenge, Flying by the Seat of our Points, was designed to push our award booking skills to the limit with a series of last minute travel challenges.
Stephen and Carrie were the game-masters who delivered last-minute destination challenges, then scored points as Greg, Nick, and Tim set out to meet each challenge before the next assignment, using their skills to achieve the best combination of frugality and luxury possible. (See the scoring criteria here).
In total, each contestant had to visit 3 last-minute destinations: 1 domestic convergence destination where they all met together, separate international divergence destinations where they all parted ways, and 1 international convergence destination where they reconvened together again. At each destination, they were given exploration challenges to force them out of their hotels and into the streets.
Summer, 2023
in January 2023, first class awards on ANA were temporarily wide open. We were able to book all five of us into ANA’s “The Suite” first class on a flight from Tokyo to San Francisco within the dates of our challenge. This became the catalyst for our Party of 5 Challenge.
We divided into two teams. Two adventures. 5 travelers. 1 referee. Team Tokyo (Stephen and Carrie) designed a five day adventure in Asia, originating in Tokyo. Team San Francisco (Nick and Tim) designed a five day adventure in the Americas, originating in San Francisco. The objective was to make great use of points and miles in order to impress the whole party of 5, especially Greg, the referee.
Fall, 2022
Nick, Stephen and Greg competed to book the most amazing 3-continent dream-trip using 3 welcome bonuses. As usual, they had a pre-determined budget and rules to stick to throughout their travels, then readers picked the winner once their trips were completed.
Several months in advance, we live-streamed a card draft where each contestant picked 3 credit card welcome offers which would make up their travel budget. No bonus could be picked twice. With their cards selected, the competitors booked the most impressive trips they could with the bonuses and perks gained from those cards.
Summer, 2021
On January 30th, Greg selected 4 Global Upgrade Certificates as one of his Delta Diamond 2020 Choice Benefits. Based on a reader idea, we turned this into a challenge. Nick could use 2 of the GUCs for himself but he would have to use 2 for Greg to travel along. This means that they could book a round trip flight to anywhere in the world that Delta (or select partners) fly. They would pay economy prices and use the GUCs to hopefully fly lie-flat business class.
Nick's main goal was to impress Greg, but we created a point system for him to track his progress as he achieved mini-goals along the way.
Fall, 2019
The goal of this challenge was simple: Get as far away as possible on a budget of 40,000 points and $400.
Greg, Nick, and Stephen were each assigned a transferable points currency. They were then allowed to use up to 40,000 points, as follows:
- Greg the Frequent Miler: 40,000 Chase Ultimate Rewards points
- Nick Reyes: 40,000 Citi ThankYou points
- Stephen Pepper: 40,000 Amex Membership Rewards points
Reader voting determined this win!
