100K Vacay midstream check-in and scoring | | Coffee Break Ep73 | 10-7-25
Frequent Miler on the Air
Frequent Miler
4.9 • 640 Ratings
🗓️ 7 October 2025
⏱️ 61 minutes
🧾️ Download transcript
Summary
Last week, Greg completed his benchmark trip using 100K Chase Ultimate Rewards points for an incredible vacation in Malta. Shortly after he returned, Tim, Nick and Stephen set out to try and out-shine his trip using 100K of the transferable points they chose to compete with. Unfortunately Tim's trip came to an early end due to an unavoidable need back home, so Nick and Stephen were left to tackle the challenge themselves. With a return deadline by the October 8th 9pm final live check-in, our more than half way finished.
This podcast episode features the full midstream live check-in where we heard trip recaps from both of our competitors and gave out grade scores for how they're doing in each main scoring category so far: Destination Wow, Applicability, Value, and Style.
(00:24) - What is 100K Vacay?
(01:31) - The Peppers summarize their travels so far, from JFK to London to Munich's Oktoberfest
(06:42) - Nick summarizes his trip from Boston to Madrid to Malaga, where he had to rebook his flight from Madrid to Malaga, but then eventually made it to the Caminito del Rey cliffside hike
(15:02) - Is Nick nervous about the budget?
(16:56) - Greg and Carrie assign grades for the "Destination Wow" category for the Peppers
(22:16) - Greg and Carrie assign grades for the "Destination Wow" category for Nick
(25:57) - Greg and Carrie assign grades for the "Applicability" category for the Peppers
(30:00) - Greg and Carrie assign grades for the "Applicability" category for Nick
(32:02) - Greg and Carrie assign grades for the "Value" category for the Peppers
(34:37) - Greg and Carrie assign grades for the "Value" category for Nick
(36:55) - Greg and Carrie assign grades for the "Style" category for the Peppers
(38:55) - Greg and Carrie assign grades for the "Style" category for Nick
(40:02) - That leaves the Peppers just ahead of Nick in every category except for "Style" so far
(41:08) - Budget usage so far
(43:06) - What was the highlight and lowlight for everyone?
(49:34) - Greg, are you surprised everyone flew to Europe?
(53:13) - What's been the biggest obstacle with your bookings so far?
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Music Credit – Beach Walk by Unicorn Heads
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Transcript
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| 0:00.0 | This is a Voyescape podcast. |
| 0:03.9 | You can find all of our travel podcasts from around the world at voyescape.com. |
| 0:11.2 | Welcome to Freakimilar's coffee break, where we focus on a single topic related to miles and points. |
| 0:16.4 | And each coffee break is limited to 20 minutes or less or your money back. |
| 0:22.9 | All right. |
| 0:23.8 | Welcome to Frequent Myler's midstream, live stream, 100K vacay check-in. |
| 0:30.9 | That was easy to say. |
| 0:34.2 | For those who have not been following along, I wanted to give a quick reminder of what 100KVay is. |
| 0:40.5 | So every year we do an annual team challenge. |
| 0:42.7 | This one, we have, Greg has just completed a challenge using 100,000 Chase Ultimate Roids points. |
| 0:51.3 | He used that to do an incredible trip to Malta. |
| 0:53.9 | And now Nick, Stephen, and Tim |
| 0:55.9 | were tasked with seeing if they could beat that trip with 100,000 points of a different |
| 1:01.6 | transferable points currency, which they got to choose themselves. Unfortunately, Tim has had |
| 1:07.0 | some family things come up. He had to go home. So now it's up to Nick and Stephen to see if they can outdo Greg's 100K vacay with Chase Ultimate Rewards points. Nick is using American Express membership rewards points and Stephen is using Capital One Miles. So now real quick, what I'd like to do is have each of you spend five minutes or so |
| 1:30.9 | giving us a summary of what you've done since kickoff. |
| 1:36.0 | We're going to start with the Peppers. |
| 1:38.6 | What have you done since kickoff? |
| 1:41.8 | Okay, so we set off from JFK. |
| 1:43.8 | We flew overnight from JFK to London on Virgin Atlantic, |
| 1:47.4 | using 6,000 virgin points. |
| 1:51.3 | And then I spent the day brewing beer and drinking beer |
... |
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