Frequent Miler on the Air 100K Vacay Livestream Kick Off | Frequent Miler on the Air Ep326 | 10-3-25
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Oct 3, 2025 Stephen Pepper, a U.K. contestant in the 100K Vacay challenge, shares his strategy for crafting replicable, budget-friendly itineraries. He dives into the excitement of starting the competition, expressing concerns over budgeting for activities. The conversation explores Greg’s benchmark trip to Malta, highlighting local cuisine, historic tours, and unique swimming spots. Stephen also discusses the impact of early departures on their competition strategies, setting the stage for an intriguing, adventure-driven challenge.
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Benchmark Trip Overview
- Greg set a benchmark 100K Vacay trip to Malta using 100,000 points and under $1,000 cash.
- He started in Detroit, positioned to New York, and flew business class to Europe then stayed four nights in Malta.
Why Chase Points Were Handled Separately
- Chase points required special rule treatment because only Chase transfers to Hyatt among the four currencies used.
- That made Hyatt's low award rates important to keep trips replicable under point constraints.
TWA Hotel And Air Serbia Flights
- Greg and Carrie visited the TWA Hotel at JFK and enjoyed retro attractions before flying to Malta.
- They then flew Air Serbia business class from JFK to Belgrade and onward to Malta.