That Passport Life with Kevin McCullough

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Winter Olympics, AI, River Cruises, and PTO

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Winter had the Northeast wrapped in a frosty embrace, giving Kevin and Linda the perfect setting to kick off the episode swapping snow‑day stories, Olympics chatter, and the beauty of untouched powder that turns neighborhoods into accidental Ansel Adams photos. With the Winter Games heading to the Milan region, they dove into nostalgic Olympic memories—complete with figure‑skating devotion and longing for the days of Howard Cosell.

Their conversation then swerved into modern travel challenges: airlines increasingly replacing humans with AI customer service while charging extra for the privilege of talking to an actual person. Kevin and Linda debated the generational divide—those who still crave human reassurance and those who can book mopeds, jet skis, and Airbnbs with zero human contact. Spoiler: Linda wants a real human on the line yesterday.

From there, they toured the world of river cruising—quaint villages, serene waterways, and slower‑paced journeys that lean toward the older crowd (Linda’s words!). Kevin dreamed aloud about Viking‑style trips, but both agreed that these voyages offer charm, not go‑karts or laser tag.

Airline drama took center stage next with the WestJet fiasco: a single removed seat row that torpedoed legroom and sparked viral outrage. The duo unpacked modern airline nickel‑and‑diming, from endless seat tiers to loyalty miles that influence nearly every booking decision Kevin now makes.

Linda wrapped things up with her Perillo Pointers, revealing an AI‑powered hack allowing travelers to stretch 11 PTO days into a whopping 41 days off by pairing vacation days with strategic holidays. It’s PTO sorcery—perfect for travelers who want more adventure without burning through all their days.

 

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