A Very Real Disney Holiday Trip: What Worked, What Didn’t, and What We’d Do Again

Walt Disney World holiday travel isn’t just twinkle lights and cocoa. It’s weather, crowds, planning choices, and a whole lot of opinions. Here’s what our December trip actually looked like — the hits, the misses, and why the details matter.

Disney's Epcot at the Holidays

If there’s one thing I always say to clients, it’s this: holiday Disney trips amplify everything.

The magic feels bigger. The crowds feel heavier. The wins feel incredible. And the misses? You notice those too.

Our December Walt Disney World trip delivered all of it — soaked shoes, unforgettable experiences, great meals, a few letdowns, and a lot of reminders about why thoughtful planning matters.

Let’s get into it.

Where We Stayed (and Why It Worked)

One Night Off‑Site: Spot X by Red Roof – International Drive

We flew in a day early and stayed off‑site before moving to Disney property. The goal was simple: save money, sleep well, and not overthink it.

Spot X by Red Roof checked those boxes.

• Comfortable bed and good pillows (underrated win)• Massive bathroom• Included breakfast• Solid location between Universal and Disney• Excellent last‑minute rate

This is the kind of hotel I recommend when clients need a functional arrival night without paying Disney prices.

On Property: Disney’s Port Orleans Riverside

Once on Disney property, we checked into Port Orleans Riverside, and it reminded me why this resort has such a loyal following.

Riverside is sprawling, quiet, and beautifully themed. Think:• Southern mansions and bayou‑style buildings• Peaceful walking paths• A resort that feels immersive without being overwhelming

We stayed in a Royal Room, which honestly surprised me.

Yes, it’s princess‑themed — but it’s subtle, detailed, and charming. Fiber‑optic fireworks in the headboard. Hidden details everywhere. A room that rewards you for paying attention.

The trade‑off: transportation can be slow depending on your building. This is where knowing bus loops and stop order matters.

Would I stay again? Yes.

Would I pick this for someone who hates walking or relies heavily on buses? Maybe not.

The Big Wins (Our Trip Hits)

🥇 Wild Africa Trek – Animal Kingdom

This was the standout experience of the entire trip.

Wild Africa Trek is a three‑hour guided experience that combines:• Backstage walking trails• Rope bridges over animal habitats• A private safari vehicle• An outdoor lunch inside the savanna

The guides were outstanding. The pace was relaxed. The group was small. And the animals were right there.

Photos are included — and they’re excellent — which meant we didn’t spend the day staring through a camera.

Worth the cost? Completely.

This is one of those experiences I recommend when clients say, “I want something special, not just rides.”

🥈 Jollywood Nights – Hollywood Studios

Jollywood Nights surprised us in the best way.

It felt like a grown‑up holiday party:• Vintage Hollywood decor• Live bands and dancers• Holiday treats and champagne cocktails• Shorter ride lines• Included PhotoPass

And then there was that moment. Jack Skellington

Up close, the Jack Skellington puppet is jaw‑dropping. The movement, facial expression, and articulation stopped an entire room mid‑breath.

Even if you’re not a Nightmare Before Christmas person — this alone was worth the time.

Cold weather aside, Jollywood Nights felt intentional, fun, and very well executed.

Rob and I at Jollywood Nights

🥉 Happily Ever After Fireworks – Magic Kingdom

We had somehow never seen Happily Ever After before this trip.

Now I understand the hype.

This isn’t just fireworks — it’s storytelling. Projections, music, lighting, lasers, and emotion packed into about 13 minutes.

Seeing it from the right spot, on the right night, with the right expectations makes all the difference.

The Misses (Because They Happen)

❌ Candlelight Processional (Weather Win… or Not)

We booked a Candlelight Processional dining package for guaranteed seating.

Then the rain came.

After delays, soaked guests, and waterlogged staging, the performance was canceled.

Disappointing? Yes.

Anyone’s fault? No.

This is holiday travel reality — especially in Florida.

❌ Transportation Delays

Port Orleans Riverside is beautiful — but buses can be inconsistent.

We had:• Long waits• Packed buses• Missed timing windows

Did we get everywhere eventually? Yes.

Was it always smooth? No.

This is exactly why resort choice matters based on how you travel, not just how a resort looks online.

❌ A Few Dining Letdowns

Not every hyped restaurant hit the mark.

Space 220: visually stunning, service slow, food just okay.

Some lounges felt rushed or overcrowded.

Nothing was terrible — but not everything lived up to expectations.

That’s normal. And manageable — if you plan buffer time and backup options.

The Little Things That Made the Trip

This is where Disney still shines.

• A towel‑folded Christmas tree left by housekeeping• Cast members interacting unexpectedly• Live musicians you stumble upon, not schedule around• Wildlife sightings at the resorts• Small moments that feel personal

These details don’t show up on a park map — but they’re why people keep coming back.

Final Takeaways (From a Travel Advisor Perspective)

This trip worked because:• We planned experiences, not just park days• We built flexibility into the schedule• We knew what not to over‑commit to• We expected weather and crowds — and adjusted

Holiday Disney trips can be incredible.

They can also be exhausting, expensive, and overwhelming if they’re not planned intentionally.

The difference is knowing what matters to you — and planning around that.

If you’re thinking about a holiday Disney trip (or wondering if it’s worth it), I’m always happy to talk it through — honestly, realistically, and with your priorities in mind.