Why Wasn’t My Vacation Magical?

Both Disneyland resort and Walt Disney World in Florida are referred to as the ‘happiest place on earth’. Engage cast members at either property in a good discussion and you’ll hear a lot about Disney magic. That is with purpose. Walt Disney wanted his properties to be magical. He wanted them to be places where people could go to enjoy a little bit of happiness without having to worry about the cares of everyday life.

So why wasn’t my vacation magical?

This is a question we travel planners hear quite often from people who don’t use our services. They return from what they had hoped would be a truly magical vacation terribly disappointed and vowing to never to return to the happiest place on earth. That’s a shame, because it doesn’t really need to be that way.

Little Planning Means Little Magic

Disney Magic is a very real thing. As annual pass holders and Florida residents, my wife and I experience it every weekend. So that begs the question of why some people don’t experience it. The answer is as simple as planning.

Planning is the key to Disney’s magic. We travel planners get the fact that some people don’t like to approach vacation with a tightly scheduled itinerary in hand. They prefer just to wander and take life as it comes. That’s a great strategy, but it comes with consequences.

For example, without at least minimal planning, there is little chance guests will enjoy all of the most sought after Disney attractions. Likewise, a lack of planning means guests might not be able to land a reservation at a key restaurant they have been dying to try.

Good planning is key to every aspect of your stay – even transportation. Planning answers the question of how to get where you’re going in the shortest amount of time and with the least amount of inconvenience.

The reality of a Disney vacation is that little planning means little magic. We wish it didn’t have to be this way, but it is. Disney is not the same property it was back in the 1970s. Things have changed considerably over the last five decades.

5 Reasons You Need to Plan

Let’s close out this post with five reasons planning is so critical to enjoying Disney magic. These are things you may not be aware of if you’re not a long-time, seasoned Disney expert:

1. Attendance Continues to Grow

One of the big things that surprises Disney guests is the size of the daily crowds. Maybe not so much in California, but attendance continues to grow here in Florida. My wife and I have noticed a big difference just in the six years we have lived here.

The fact is that there are a lot more people now trying to enjoy the same property. Planning helps you navigate the crowds and enjoy what you want to enjoy without having to stress over every little thing.

2. Waiting Is a Reality

Spending all day waiting in lines is a good way to kill the magic quickly. Here’s the thing: if you go into either Disney property without a plan in place, you’re going to spend most of your day waiting in lines. On the other hand, a good plan minimizes wait time. It also keeps you moving, giving you more opportunities to see and do more things.

3. Transportation Takes Time

Another reality that surprises the unprepared is that transportation takes time. Whether you’re traveling from an off-site hotel to Disneyland or an on-site resort to one of the Walt Disney World parks, you are not going to make the journey in 10 minutes. You have to plan 30 to 40 minutes for most journeys.

Unfortunately, not planning your transportation is a good way to miss a dinner reservation. It’s a good way to lose time when you’re trying to take advantage of Park Hopper tickets.

4. You Can’t Do It All

Next up, there is more to do in a single Disney Park than most families can accomplish in one day. That makes it easy to feel overwhelmed. Going into a park without proper planning can leave you feeling lost and frustrated. As you try to navigate your way around a huge park crammed with tens of thousands of people, that sense of being overwhelmed only grows.

On the other hand, there are no worries with a plan in hand. You’re not overwhelmed because you know exactly what you’re doing. Planning takes the edge off by making sure you get to experience the things most important to you. Every additional experience then becomes a delightful bonus you weren’t expecting.

5. Fast Passes Are Harder to Come By

Last but not least are fast passes. In both California and Florida, growing attendance is making fast passes harder to come by. California guests have a slight advantage in that fast passes can only be obtained at the park on the day of your visit. That puts everyone on a level playing field. In Florida though, things are different.

Crowd size and demand have forced Disney World to make fast passes available in advance. And believe me when I say that getting your fast passes well ahead of your actual visit is the way to go. If you wait until the day you arrive, you’re going to be left out.

I cringe whenever we’re on a bus or the monorail listening to guests talk about their plans to get fast passes in the park. I know they are in for a big disappointment, but there’s nothing to be done. They waited too long. If they had worked with a travel planner several months out, it’s very possible they could have all the fast passes they wanted.

Disneyland and Walt Disney World have both changed. But that doesn’t mean the magic is gone. It’s not. When someone leaves a Disney vacation and asks why it wasn’t magical, the answer almost boils down to a lack of planning. Plan it right and you will have the magical vacation of a lifetime. We vacation planners know. We experience it all the time.

Matt and Ellen Gerwitz – Travel Agents from Dreamers Do Travels

Scroll to Top

Kim Daley

Travel Specialist

From… Orlando, FL

With DDT since… 2015
Favorite Destination/Resort you’ve been to…

Disney Cruise Line and traveling EuropeDream Vacation… Adventures By Disney Private Jet Tour


I love to book… Disney Cruise Line, Royal Caribbean Group, Sandals and Beaches Resorts

Erica Dipyatic

Travel Specialist

From… Cranberry, PA
With DDT since… 2024
Favorite Destination/Resort you’ve been to… Croatia, or a Virgin Voyages cruise
Dream Vacation… Island and port hoping in the Mediterranean, down the Croatian coast
I love to book… Girls/guys trips, Couples getaways, Group adventures, Cruises and Croatia

Skyler Gring

Travel Specialist

From… Mt. Lebanon, PA
With DDT since… 2024
Favorite Destination/Resort you’ve been to… Walt Disney World and countries in Europe – most recently, Portugal
Dream Vacation… Adventures by Disney River Cruise in Germany to see the beautiful German towns at Christmas with my family
I love to book… Disney Destinations

Kaylee Shoats

Travel Specialist

From… Jefferson Hills, PA
With DDT since… 2024
Favorite Destination/Resort you’ve been to… Italy (but also love a good Walt Disney World trip)
Dream Vacation… Greece, and Disney’s Aulani Resort
I love to book… Disney Destinations and cruises

Krystle Callari

Travel Specialist

From… Buffalo, NY
With DDT since… 2024
Favorite Destination/Resort you’ve been to… Disney Cruise Line’s Private Island Castaway Cay, and Skagway, Alaska
Dream Vacation… Polynesia – Hawaii and New Zealand
I love to book… Walt Disney World, Disney Cruise Line, Universal Parks and Resorts Vacations

Nicole Kornblatt

Travel Specialist

From… Harrisonburg, Virginia
With DDT since… 2024
Favorite Destination/Resort you’ve been to… Sandals Royal Bahamian
Dream Vacation… Over the water bungalow!!
I love to book… Sandals and Beaches Resorts, Disney Cruise Line, Viking River Cruises, Destination Vow Renewals

Amy Rocke

Travel Specialist

From… Mars, PA
With DDT since… 2023
Favorite Destination… Surf City, NC
Dream Vacation… Bora Bora
I love to book… Disney Destinations, Sandals Resorts, Royal Caribbean Cruise Line

Emily Lamphere

Travel Specialist

From… Pittsburgh, PA
With DDT since… 2023
Favorite Destination/Resort you’ve been to…Beaches Turks & Caicos
Dream Vacation… Amalfi Coast
I love to book… Disney Destinations, Universal Parks and Resorts Vacations, Sandals and Beaches Resorts

Amber Martin

Travel Specialist

From… Lexington, Kentucky
With DDT since… 2023
Favorite Destination/Resort you’ve been to…Walt Disney World, The Polynesian Village
Dream Vacation… A Mediterranean Cruise
I love to book… Walt Disney World, Disney Cruise Line, Sandals Resorts

Bridget Henry

Travel Specialist

From… Orlando, FL
With DDT since… 2022
Favorite Destination/Resort you’ve been to… Japan
Dream Vacation… I would love to see Antarctica and play with the penguins!
I love to book… Disney Destinations, Cruises, International travel

Kim Daley

Travel Specialist

From…Peters Twp., PA
With DDT since… 2022
My favorite Destination/Resort you’ve been to… Walt Disney World
Dream Vacation… Bora Bora
I love to book… Disney Destinations, Universal Parks and Resorts Vacations

Jenna Powell

Travel Specialist

From… McMurray, PA
With DDT since… 2022
Favorite Destination/Resort you’ve been to… Italy
Dream Vacation… A river cruise on the Rhine River
I love to book… European vacations, Disney Destinations, Universal Parks and Resorts Vacations

Olivia Wegner

Travel Specialist

From… Orlando, FL
With DDT since… 2022
Favorite Destination/Resort you’ve been to… Sandals Dunn’s River in Jamaica
Dream Vacation… Mediterranean Disney cruise
I love to book… Disney Parks and Disney Cruises, Sandals Resorts, Family All-Inclusive Resorts

Katie Mattison

Travel Specialist

From… Saint Petersburg, FL
With DDT since… 2022
Favorite Destination/Resort you’ve been to… Bermuda
Dream Vacation… World Cruise aboard a luxury ship
I love to book… Cruises, Groups, Tropical and European destinations

Brittany Digon

Travel Specialist

From… Washington, PA
With DDT since… 2021
Favorite Destination/Resort you’ve been to… Walt Disney World
Dream Vacation…Disney Cruise on the newest ship, the Disney Treasure
I love to book… Disney Destinations, Sandals Resorts, Universal Parks and Resorts Vacations

Madison Ott

Travel Specialist

From… Estero, FL
With DDT since… 2021
Favorite place I’ve been… London, England
Dream vacation… Antarctica
I love to book… Disney Destinations, Universal Parks & Resorts

Kaly Gluth

Travel Specialist

From… Amity, PA
With DDT since… 2021
Favorite Destination/Resort you’ve been to… Sandals Royal Bahamian
Dream Vacation… A luxurious all-inclusive in the Caribbean or island-hopping in the Cyclades
I love to book… Sandals and Beaches Resorts, Disney Destinations

Beth Kleist

Travel Specialist

From… Monroeville, PA – 12 Miles East of Pittsburgh
With DDT since… 2020
Favorite Destination/Resort you’ve been to…10 Day Cruise, over Christmas, to 5 different Islands.
Dream Vacation… Over-the-water Bungalow in Bora Bora!
I love to book… Cruises, Disney Destinations, All-Inclusive Resorts

RaeAnn McFall

Travel Specialist

From… Bethel Park, PA
With DDT since… 2019
Favorite Destination/Resort you’ve been to… Sandals LaToc and Disney Cruise
Dream Vacation… Greece
I love to book… All-Inclusive Resorts, Disney Destinations, Sandals Resorts

Bethanne Kania

Travel Specialist

From… Pittsburgh, PA
With DDT since… 2018
Favorite Destination/Resort you’ve been to… Atlantis in the Bahamas
Dream Vacation… Turks & Caicos
I love to book… Disney Destinations, Sandals Resorts

Krissy Penn

CTA | Travel Specialist

From… Pittsburgh, PA
With DDT since… 2018
Favorite Destination/Resort you’ve been to… Sandals Royal Curaçao
Dream Vacation… A World Cruise to see and experience EVERYWHERE!
I love to book… Disney Destinations, All-Inclusive Resorts – especially Sandals Resorts, AmaWaterways

Erica McCutcheon

Travel Specialist | Founding Member

From… Chicago, Illinois
With DDT since… 2016
Favorite Destination/Resort you’ve been to… Walt Disney World – Contemporary Resort theme park view, and Maui, Hawaii – Fairmont Kea Lani
Dream Vacation… Disney’s Aulani Resort & Spa, and a Disney cruise to Norway and Scotland
Love to book… Walt Disney World and Disney Cruise Line

Miranda Masters

Travel Specialist | Founding Member

From… Chattanooga, TN
With DDT since… 2016
Favorite Destination/Resort you’ve been to… Edinburgh, Scotland
Dream Vacation… Switzerland!
I love to book… City travel, Disney Destinations, National Park trips, European trips, girls trips

Celeste Lazzaro

Travel Specialist | Founding Member

From… Canonsburg, PA
With DDT since… 2016
Favorite destination/resort you’ve been to… Ritz Carlton Kapalua
Dream Vacation… Overwater Bungalow Suite at the Four Seasons Bora Bora
I love to book… Walt Disney World, Sandals and Beaches Resorts, Disney Cruise Line

Kristi Metcalfe

Travel Specialist | Founding Member

From… Hillsborough, NJ
With DDT since… (year) 2016
Favorite Destination/Resort you’ve been to… Sandals St. Lucia
Dream Vacation… Hawaii with the kids
I love to book… Sandals and Beaches Resorts, Disney Destinations, Inclusive Collection by Hyatt

Ellen Gerwitz

Travel Specialist | Founding Member

From… Orlando, FL
With DDT since… 2016
Favorite Destination/Resort you’ve been to… Walt Disney World’s Coronado Springs Resort
Dream Vacation… Trans-Atlantic Cruise from Europe to U.S. (and we have it booked for 2025!)
I love to book… Walt Disney World, Disney Cruise Line, Sandals and Beaches Resorts

Christine Chimento

Lead Travel Specialist

From… Staten Island, NY
With DDT since… 2023
Favorite Destination/Resort you’ve been to… Four Seasons Resort Bora Bora
Dream Vacation… Greek islands & Capri
I love to book… Walt Disney World, Aruba, custom trips such as Napa Valley

Chelsea Volkar

Lead Travel Specialist

From… Greensburg, PA
With DDT since… 2020
Favorite Destination/Resort you’ve been to… Tied for Disney’s Polynesian Resort at Walt Disney World, and Disney’s Grand Californian at Disneyland
Dream Vacation… Alaskan Cruise on DCL
I love to book… Walt Disney World, Disneyland, Disney Cruise Line

Jen Wolstoncroft

Senior Lead Travel Specialist

From… Pittsburgh, PA
With DDT since… 2019
Favorite Destination/Resort you’ve been to… Disney Wish – Disney’s Castaway Cay
Dream Vacation… Travel throughout Europe- land and sea
I love to book… Disney Destinations, Universal Parks and Resorts Vacations, Royal Caribbean Cruise Line

Jess Devore

Lead Travel Specialist | Founding Member

From… Washington, PA
With DDT since… 2016
Favorite Destination/Resort you’ve been to… Beaches Turks and Caicos
Dream Vacation… Italy
I love to book… Sandals and Beaches Resorts, All-Inclusive Resorts, Disney Destinations

Kristie Cobleigh

Top Senior Lead Travel Specialist | Founding Member

From… Canonsburg, Pennsylvania
With DDT since… 2016
Favorite Destination/Resort you’ve been to… Disney Cruise to Northern Europe including England, Iceland, Norway, France and Denmark
Dream Vacation… Australia or Bora Bora
I love to book… Disney Destinations, Sandals and Beaches Resorts, Royal Caribbean Cruise Line

Alex Ballenger

Onboarding & Training Specialist | Travel Specialist | Founding Member

From… Orlando, FL
With DDT since… 2015
Favorite Destination/Resort you’ve been to… Disney Cruise Line and traveling Europe
Dream Vacation… Adventures By Disney Private Jet Tour
I love to book… Disney Cruise Line, Royal Caribbean Group, Sandals and Beaches Resorts.

Liz & Bill Winter

Owners | Founders

From… Venetia, PA
Established Dreamers Do Travels in… 2015
Favorite Destination/Resort you’ve been to…
Liz – Beaches Turks & Caicos and Disney Cruise Line
Bill – Disney Cruise Line – especially Disney’s Castaway Cay
Dream Vacation… a really long Disney cruise, sailing concierge level!
I love to book… Disney Cruise Line, Sandals and Beaches Resorts

Liz & Bill Winter

Owners | Founders

From… Venetia, PA
Established Dreamers Do Travels in… 2015
Favorite Destination/Resort you’ve been to…
Liz – Beaches Turks & Caicos and Disney Cruise Line
Bill – Disney Cruise Line – especially Disney’s Castaway Cay
Dream Vacation… a really long Disney cruise, sailing concierge level!
I love to book… Disney Cruise Line, Sandals and Beaches Resorts