Stephen Pepper
Frequent Miler contributor and frequent challenge participant known for experiential trips; on this episode he competed in the 100K Vacay challenge and was crowned the winner.
Best podcasts with Stephen Pepper
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8 snips
Oct 7, 2025 • 1h 1min
100K Vacay midstream check-in and scoring | | Coffee Break Ep73 | 10-7-25
This week, Stephen Pepper, a contestant in the 100K Vacay challenge, shares his travel experiences from London to Munich's Oktoberfest. Despite flight delays, Stephen's highlights include local interactions and brewing beer at the festival. He discusses the replicability of their adventures, while competitor Nick recounts his hike at Caminito del Rey and a missed connection in Madrid. The judges grade their trips on factors like 'Destination Wow' and 'Value,' with both travelers showcasing their unique adventures and clever point redemptions.
4 snips
Oct 3, 2025 • 1h 11min
100K Vacay Livestream Kick Off | Frequent Miler on the Air Ep326 | 10-3-25
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.
