Behind The Magic: #2 Resort and Flight Picks For A 5-Day Disney Holiday!

August 1, 2025 admin

Behind the Magic: Post #2 Inside My Disney Trip Plans Series, where I give you a front-row seat to how I plan my Walt Disney World vacations! If you’ve ever felt overwhelmed by Disney planning, this series is your new best friend. I’ll be sharing all the nitty-gritty details—real decisions, real dilemmas, and my best tips—so you can plan your own magical trip with less stress.

If you’re dreaming of a cozy, holiday-season escape to Walt Disney World, this one’s for you! This trip is still early in the planning process (we haven’t hit our ADR window yet!), but I’ve already made a few big strategic decisions that are worth sharing—especially if you’re trying to save money and make the most of your time.

Trip Snapshot

Season: Winter Holidays (6 days / 5 nights total)
Resorts: 1 night at All-Star Sports, 4 nights at Coronado Springs (Gran Destino Tower)
Guests: Me and my daughter
Planning Focus: Resort strategy, flight savings, holiday extras

Why I Booked the Hotel Before the Flight

When I first started planning this trip, my focus was all about finding a magical holiday stay without breaking the bank. I locked in Coronado Springs at Gran Destino Tower first—I knew I wanted that beautiful holiday ambiance with upgraded amenities but without deluxe pricing.

Gran Destino has a more boutique hotel feel than most moderates, and it really shines during the holiday season with its elegant decor and amazing rooftop dining.

The Flight Deal That Changed Everything

Here’s where a little flexibility turned into serious savings: when I went to book our flights, I found a much cheaper option that arrived a day earlier than our Coronado reservation.

Instead of adjusting the main resort stay (and possibly losing that room type), I booked a one-night stay at Disney’s All-Star Sports Resort.

Not only did we save big on flights, but we also get a bonus Disney day! And Bell Services will move our luggage to Coronado for us the next morning.

Insider Tip: One-night stays at value resorts are great for maximizing park time or grabbing great flight deals.

Bonus Perk: Free Water Park Day!

Disney’s latest promo offers complimentary water park entry on check-in day for guests staying at a Disney Resort. That means we can splash into our vacation at Blizzard Beach or Typhoon Lagoon before even setting foot in the parks!

We’ll likely spend that day at Blizzard Beach (holiday theming + lazy river vibes!) while our luggage is being transferred from All Star Sports to Coronado Springs.

Holiday Highlight: Mickey’s Very Merry Christmas Party

While most of our park plans are still TBD, one thing I had to book early was Mickey’s Very Merry Christmas Party at Magic Kingdom.

This special-ticketed event is filled with:

Holiday parades
Exclusive character meet-and-greets
Free cookies and cocoa
Snow on Main Street – yes, snow in Florida!

We’ve planned this for our third night to give us time to rest up beforehand and soak it all in without feeling rushed.

Tip: These party tickets can sell out! You can get them directly from Disney World.

Gingerbread House at the Grand Floridian Resort

What’s Next in Our Planning Timeline

We’re still outside our 60-day window, but here’s what I’m watching for next:

ADRs: We’ll prioritize rooftop dining at Toledo and maybe a character breakfast
Park reservations + Park Hopper upgrade decision
Holiday outfit planning + themed photo shoot ideas

Disney Holiday Essentials for This Trip

Planning a holiday Disney trip? I’d love to hear your must-dos or help you brainstorm ideas. Leave a comment below or tag me on Instagram with your holiday planning questions!

Stay tuned for the next entry where we finalize ADR picks and share our Lightning Lane strategy for the busy holiday season.