

Family Vacations Edition w/ Kevin Ryan & H. Foley
Aug 18, 2025
Dive into hilarious tales of family vacations gone awry, from unexpected detours to chaos in cramped accommodations. The hosts share funny childhood memories and the nostalgia of past trips, juxtaposed with their current adult perspectives on travel. Engaging anecdotes highlight the absurdities of group travel and the often comedic dynamics that unfold among family members. With playful banter and relatable stories, the conversation brings a humorous touch to the trials and tribulations of vacationing with loved ones.
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Payday-Planned Getaways
- Kevin Ryan timed vacations around paydays and would book travel immediately after getting paid to afford trips.
- He lived tight for weeks prior so he could leave with cash in hand for the flight and airport burger.
Weekend Shore Trips Only
- Kevin describes family trips as short Friday-to-Sunday breaks because his dad's construction business couldn't leave work.
- Weeklong vacations were rare due to slow contractor payments and cash flow constraints.
Wildwood/Ocean City Reality TV
- Kevin recounts an Ocean City, MD vacation where rain trapped him inside and family dynamics felt like reality TV.
- Large shared rental houses exposed tensions and made porch-watching neighbors a spectacle.