A Mom's Perspective

Our Vacation Doesn't Have to Look Like Everyone Else's

Learning to Pivot: Traveling With My Son

Our vacations haven't always looked like everyone else's.

There have been meltdowns, unexpected changes, moments when we've had to leave early, and plenty of times when Plan A didn't work.

But there have also been some pretty amazing memories.

Traveling with my son has taught me a lot about vacations—and even more about myself.

Finding What Worked for Our Family

When my son was younger, I was nervous about everything.

I worried about meltdowns. I worried about him running off. I worried about whether I could get him under control and get us out of a situation if things went wrong.

My parents came on many of our trips during those years. Having them there meant my daughter could still enjoy the vacation if my son was having a difficult time.

We did Disney a few times when he was younger, and he actually did pretty well.

But around ages 10 to 13, we started seeing more sensory issues. Disney World was just too overwhelming for him, so we put Disney on the back burner for a while.

He loved the beach, though. So we did beach trips. We tried things like Pirates Voyage in Myrtle Beach, and surprisingly, he handled the dinner show pretty well.

Then, in 2015, we tried something different.
We went to Dollywood.
And he loved it.
So much so that we became season pass holders from 2015 through 2020.
That's where we discovered something else about my son.
He's a thrill ride junkie.

He loved the rides, but he also loved the shows.

Over those years, we had some really good trips and some not-so-good trips. But somewhere along the way, we found our rhythm.

We learned what worked for him. And we learned that sometimes, you just have to pivot.

I still remember one day when the train at Dollywood shut down.
My son did not handle that well.

We ended up having to work our way out of the park early, promising him a toy from the store on the way out.

As we were leaving, he kept saying,

"Train broken! OhNo!"

It wasn't the day we had planned. But we got through it.

And that experience taught me something I would carry with me into every vacation after that:

Plan A is great. But sometimes you need Plan B. And maybe even Plan C.

And that's okay.

Finding Our Way Back to Disney

Eventually, we decided to try Disney again. We surprised my son with a Disney World trip for Christmas, and we went the following May.

He loved it.

This time, we didn't give him every single detail of what we were doing. We gave him a general idea of what the day would look like.

That worked better for us. He loved the characters. He loved the monorail, the boats, and the buses.

And I learned something important.
He didn't need to know every detail.
He just needed to know enough to feel comfortable with what was coming.

We also learned to prepare for the things we couldn't control.
Shows get canceled.
Rides close.
Plans change.

So on our next Disney trip, I tried to be better prepared for those moments. Not because I expected something to go wrong, but because I knew that if it did, we could handle it.

A Trip I'll Always Remember

Our November 2025 Disney trip is probably the trip I'm most proud of.

It was just me, my daughter, and my son.
And overall, it went really well.

Could we have done some things differently?
Absolutely.

I wish we had used DAS a little more during the Christmas party, for example.

But what really stood out to me was how helpful the Cast Members were throughout the trip. Even when we weren't using DAS, we had Cast Members who were kind, patient, and tried to help us when things got difficult.

A Note From Ann

This is exactly why I walk every family through DAS and Lightning Lane before their first trip—so you already have a plan in place before you ever set foot in the park.

And then there was another day at Hollywood Studios.
We were waiting for our return time for Slinky Dog.
My son had a meltdown.

A few years earlier, that probably would have been the moment when I thought, we're going to have to leave, this is not going to be pretty.

But this time, we had a Plan B.
We went to get a drink.
We looked at some of the souvenir booths.
We just found something to occupy the time.
He wasn't happy.

But Mom was calm.

And that made a difference. He could be unhappy without me becoming overwhelmed by it.

Eventually, we got back in line. And when he got on Slinky Dog and that smile came across his face, it was worth that little bit of frustration. The rest of the evening was amazing.

I remember thinking about how different that moment was from the way I might have handled it years earlier.

The mom I was back then might have thought, the day is over.

The mom I am today thought,

"Okay. That didn't work. What's next?"

That's what I've learned. Sometimes you just have to pivot.

What I Would Tell the Mom Who Is Worried

If you're the mom who is sitting there wondering if you can actually take that vacation, I understand.

I've been that mom.
I've worried about the meltdown.
I've worried about what other people would think.
I've worried about having to leave.
I've worried about whether everyone else in the family would still get to enjoy their vacation.

And I can't promise you that everything will go perfectly.
It probably won't.
But I've learned that it doesn't have to.

It's okay to change your plans.
It's okay to take the break.
Get the snack.
Get the drink.
Go see the show you weren't planning on seeing.
Do things at your child's pace.
And if Plan A doesn't work, try Plan B.

Your child can be unhappy, and you can still stay calm. Sometimes having a few favorite things, activities, or solutions ready to go can help diffuse a difficult moment.

And sometimes you just need to step away for a little while.
That's okay, too.

Mom, it is okay to take the break.

You don't have to do everything.
You don't have to make the vacation look like everyone else's.
You just need to find what works for your family.
And believe me, you can learn as you go.
I did.

A Little Something to Help You Prepare

One of the things I've learned through all of our trips is that being prepared can make a difference.

You can't plan for everything.
Trust me, I've tried!

But having some of the things your family may need packed and ready can take a little bit of stress off your shoulders. So I put together a Free Vacation Packing Guide to help you get started.

Get the Free Packing Guide

I hope it helps you feel a little more prepared and a little more confident as you get ready for your next adventure.

Because your vacation doesn't have to look like everyone else's.
It just needs to work for your family.

And if you're the mom who is worried about whether you can do this...

You got this.

All the Best,
Ann

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The REAL Best Time to Visit Disney World & Universal Orlando Crowds, weather, and prices — decoded 🔎

​If there's one question I get more than any other, it's this: "Ann, when should we go?" I love that question, because the real answer isn't one date on a calendar — it's three questions rolled into one: how crowded will it be, how comfortable will the weather be, and how much is this going to cost you. Let's walk through all three, so you can pick dates that actually fit your family instead of guessing.

🎢 First, Let's Talk Crowds

Both Disney World and Universal Orlando follow a pretty predictable rhythm tied to school schedules and holidays. Here's the pattern I watch for my own clients:

Quieter windows worth circling:

• Mid-January through early February (right after the New Year's rush)
• September, especially the weeks right after Labor Day
• Early November, before Thanksgiving travel picks up
• The first two weeks of December, before the 24th

Dates to plan around, not for:

• Christmas week through New Year's Day (the busiest stretch of the year, hands down)
• Spring Break (mid-March through mid-April, varies by school district)
• The week surrounding July 4th
• Thanksgiving week and Presidents' Day weekend

One insider tip that holds true almost every week of the year: Tuesday through Thursday are consistently quieter than weekends at both destinations. If your schedule is flexible, shifting your park days mid-week can make a bigger difference than shifting your whole trip by a month.

☀️ Now, the Weather

Orlando doesn't have four dramatic seasons, but it definitely has moods:

• Winter (Dec–Feb): Peak comfort season — mild days, cool evenings, and the lowest odds of a surprise downpour. Pack a light layer for mornings.
• Spring (Mar–May): Warm and pleasant early on, with humidity creeping up by May. This overlaps with Spring Break, so nice weather often means bigger crowds too.
• Summer (Jun–Aug): Hot, humid, and prone to daily afternoon thunderstorms. This is also the start of hurricane season, worth watching if you're traveling June through November.
• Fall (Sep–Nov): Still warm in September, with hurricane season at its peak, but it cools off nicely by November. Late September through early November is a bit of a hidden gem — lower crowds and easing heat.

💰 What About Prices?

Here's where it gets a little more nuanced. Both Disney and Universal now use date-based ticket pricing, so a single day of park admission can cost more on a busy day and less on a quiet one. Resort and room discounts also come out in seasonal waves, often released several months ahead of the travel dates they cover, with deeper savings for longer stays.

The pattern that tends to hold true: the same off-peak windows that are quieter and more comfortable weather-wise also tend to line up with the better room discounts and lower per-day ticket pricing. It's not a guarantee every single year, but it's strong enough that it's the first thing I check when a client gives me flexible dates.

🌟 My Favorite "Sweet Spot" Windows

If I had to pick the windows that check the most boxes — lower crowds, more comfortable weather, and better odds of a good discount — I'd point you toward mid-January through early February or the first half of December. Early-to-mid September is a close third if you can handle a little extra warmth for a lot fewer lines.

Every family's "best" time is a little different depending on school schedules, budget, and how much heat you can tolerate. That's the fun part of my job — matching real dates to your real life, then keeping an eye out for the discount windows that apply to your trip so you don't have to track all of this yourself.

Ready to Find Your Perfect Dates?

📅 Book a Time on My Calendar💌 Get a Vacation Quote

All the Best,
Ann