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Behind the Magic Trip Diary #4: Planning Our Holiday Trip Park Days, Resort Hopping & Must-Dos!

It’s time for another update in my Behind the Magic planning series. This time, we’re diving back into the mother-daughter holiday trip to Walt Disney World! We’re still a few days away from our ADR window, but planning is well underway.

This trip is all about slowing down, soaking up the seasonal atmosphere, and enjoying some extra holiday pixie dust, so our itinerary is shaping up to reflect that vibe. Here’s how I’m making decisions now to ensure a magical and (relatively) stress-free trip later!


Gingerbread house at the Grand Floridian

Big Picture Priorities

This is a December trip, so we’re factoring in:

  • Holiday crowds
  • Cooler temps
  • Shorter park hours (especially for non-party nights)
  • Seasonal overlays and special experiences

Instead of trying to “do it all,” we’re choosing a balance of:

  • 1 park day at Disney’s Hollywood Studios
  • 1 resort day to enjoy Gran Destino Tower and some poolside relaxation
  • 1 deluxe resort-hopping day to tour Christmas decor
  • 1 party day at Mickey’s Very Merry Christmas Party

We may add another park day if we feel up for it, but this loose structure gives us freedom and focus. We’ve don’t think we will be adding a park hopper for this trip.


Holiday Festive Chocolate Mickey Shaped Pop

Using Crowd Calendars to Choose Park Days

I’m currently comparing crowd calendars from:

Hollywood Studios is known to be a busy park during the holidays, especially with all the festive offerings in Toy Story Land and Galaxy’s Edge. I’m planning our Hollywood Studios day for a Tuesday or Wednesday to avoid the peak weekend crowds.


🎄 Deluxe Resort Holiday Tour

We’re dedicating one day to visiting:

  • Disney’s Grand Floridian (iconic gingerbread house!)
  • Disney’s Polynesian Resort (laid back, tropical vibes)
  • Disney’s Contemporary Resort (easy monorail access + snacks)
  • Disney’s Wilderness Lodge (cozy Christmas feel + Christmas Tree photo ops)

We’ll use the monorail + boat transport to hop between locations and enjoy a crowd-free, relaxed holiday day.

Tip: I always pack a portable phone charger and holiday-themed outfits for resort photo days. You’ll take more pics than you think!


Grand Floridian Holiday Decor Main Lobby

Planning Our Park Must-Dos (So Far)

We’re still refining, but here are a few early priorities:

Hollywood Studios

  • Mickey & Minnie’s Runaway Railway
  • Hollywood Tower of Terror
  • Lunch at 50s Prime Time or Sci-Fi Dine-In
  • Frozen Sing-Along (holiday edition!)
  • Seasonal snacks + holiday merch stops

Magic Kingdom (Christmas Party Night)

  • Snowfall on Main Street
  • Minnie’s Wonderful Christmastime Fireworks
  • Cookies, Cocoa, and Holiday Treats
  • Mickey’s Once Upon a Christmastime Parade
  • Ride Jingle Cruise and Haunted Mansion
Pathway marking Christmas Party

Next Up on the Planning Timeline

  • Finalize park days and party date
  • Secure ADRs (Maya Grill, Sci-Fi Dine-In, possible character breakfast)
  • Outfit planning + resort day itinerary
  • Confirm travel times, water park logistics, and more

This is the fun part of trip planning—where the vision starts to feel real!

Next in the series: It’s time to shift gears back to our long weekend couple’s trip and review the final plans.

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