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September 8, 2025 22 mins

Read the full show notes for this episode HERE!

If the words “fun” and “relaxing” don’t describe your last Disney trip, this episode is your rescue plan. 

I’m breaking down what most families get wrong when planning a Disney trip - and how a few simple shifts in Disney World planning (hi, transportation and dining, I’m looking at you) can make your Disney trip feel human again. If you’re ready to actually plan your Disney vacation without turning into your family’s frazzled tour guide, this one’s for you.

In today’s chat, I’m sharing the exact mistakes I see over and why a tiny bit of upfront Walt Disney World planning saves you hours of stress later. 

What we cover (and why it matters):

  • The “sketch before you book” method: how a 10-minute day map beats weeks of chaotic Disney World planning…
  • Resort reality check: why picking by price or pool can sabotage planning a Disney trip - and the easy location-first filter I use
  • The mobile-order timing trick that turns your Disney trip from frantic to calm…
  • When to book dining (and when not to), so planning a Disney trip doesn’t lock you into a zig-zag itinerary you’ll regret…
  • The one question that instantly improves your resort choice when you plan your Disney vacation
  • Why there’s no “perfect age,” to take your kids on a Disney trip

These are all of the things I wish I had known when I started Walt Disney World planning with a diaper bag and a dream.

Question for you: what part of Disney World planning stresses you out the most right now - resort location, transportation, or dining windows?... Let me know over on IG:  @somewhereworthwhile.

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Podcast music by Podington Bear, track: 'Filaments', licensed under CC BY-NC, courtesy of Free Music Archive.

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