Road Trips, Chaos, and Disney Hacks: Our Family Vacation Playbook episode artwork

EPISODE · Sep 9, 2025 · 35 MIN

Road Trips, Chaos, and Disney Hacks: Our Family Vacation Playbook

from We Should Probably Edit This — But We Won't

When you’re raising kids, vacations are less about perfection and more about presence. We talk through our most memorable trips—from 22-hour drives to Florida (hello, Disney employee pass) to Maine island cottages with pets in tow—and the systems that helped us survive: packing snacks, bringing backup water/towels, rigging a portable TV/VCR, and budgeting with creativity. We also share a hard-earned lesson: if you’re lucky enough to go, disconnect and actually be with your people. Now as empty nesters, we’re relearning how to choose a destination, set a budget, and just…book it.You’ll hear about:Budget hacks (free lodging with family, passes, packed lunches)Long-haul road trip logistics with kids + petsThe cat-on-the-pillow incident (never again 😅)Holiday flight chaos (the legendary “hacking guy”)Why being present beats being “productive” on vacationOur struggle to plan trips as a duo—and how we’re fixing it

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Road Trips, Chaos, and Disney Hacks: Our Family Vacation Playbook

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