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How to Plan the Perfect Trip to Disney

it may be a “small world,” but Disney is a big trip

They say Disney World is the happiest place on Earth. It can be—if you plan your trip well! But there’s so much to know when it comes to organizing a trip of this magnitude, especially since COVID-19 turned everything upside down. Here’s your “how to” guide for this one of a kind trip.


Former Disney planner Angelyn Horrell (now DFWChild’s audience development director) says you should start your planning your vacation six months to one year out. You can try to arrange a trip in less, but you could run into things being sold out. By booking well in advance, you’ll have better luck getting access to everything you want.

As far as the best time of year to make your trip, Shannon Albert—travel planner with WDW Prep School—says the answer is a bit harder to nail down right now.

“The best time of year to visit is normally a fairly easy question for us to answer, but it’s tricky to predict currently—not only for us, but I imagine for Disney as well,” Albert says. “Right now, we are projecting that crowds will mostly increase throughout the year as more and more people feel safe to travel. People traveling now will see lighter crowds but also fewer things open. People traveling later this year will likely have more things open, but more people traveling.”

Holiday breaks tend to have moderate to heavy crowds; Albert is expecting that will hold true in 2021. She expects the best balance—smaller crowds and open attractions—is likely to be in September. “Historically, fewer people are traveling, but Disney will have reopened many of the things that are closed now,” Albert says.

(For a more detailed breakdown of Albert’s crowd expectations, visit WDW Prep School’s crowd calendar at wdwprepschool.com/disney-world-crowd-calendar.)

If you’ve already decided when to go, have you thought about how long you’ll stay? Is there a typical length for a Disney World trip? Albert says that depends on your family. For a group of first-timers, she recommends a week. “That allows for plenty of time in the parks, some resort time, a chance to rest between long park days and so on,” she explains.

If you’ve been there before, reflect on your trip. Were you rushed? Will you want to visit all the same parks? Plan accordingly.

Courtney Tennyson, the Grapevine mom of a toddler, strongly recommends you work with a Disney travel agent. “They give you all the ins and outs beforehand,” she explains. Plus, it’s free to use a Disney travel agent. Horrell says they will watch for discounts and share any valuable tips for planning with you. Of course, it doesn’t hurt to do your own research as well.


Disney is known for drawing crowds, so your hotel options are extensive—both on Disney property and throughout the city. In fact, there are more than 450 hotels and resorts in Orlando; visitorlando.com/places-to-stay has a breakdown of your choices.

Tennyson recommends that access to Disney’s monorail system be a major consideration in choosing where to stay, especially if you have a little one. When Tennyson visited Disney World with her family September 2020, her son Wyatt was 18 months old.

“With a baby, staying on the property or somewhere with monorail access made getting back and forth very easy,” she says. It’s also helpful if you have a big group.

Resorts with monorail service include Disney’s Contemporary Resort and Disney’s Grand Floridian Resort & Spa; service is normally available to Disney’s Polynesian Village Resort, but that site is currently undergoing refurbishment.


Take your child’s age, height and personality into account when sketching out your park agenda. Not sure about what rides would be best? The Disney World website lists out its attractions with information including required height, whether it’s a fast or slow ride, if it has any drops, etc.

And if your child has historically not done well with costumed characters, don’t force it. Are they sensitive to loud noises? Maybe your family should head out before the fireworks show. This will help prevent potential tantrums or frustrations for everyone.

Horrell says it’s also a good idea (especially if you have little ones) to schedule your mornings but leave the afternoons flexible. “This will allow for your family to either keep going if the kids are happy, or open for returning to the hotel for a nap if needed,” she points out.

Now, we know you don’t want to be carrying a kiddo on your hip the whole day. If you need a stroller, you can bring your own or even rent one from a local company that will deliver it to your hotel. “You can also rent one in the parks,” Horrell says.

Another pro tip: Make sure you bring something that will help you easily identify your stroller when it’s parked with others—attach a bandana, scarf or something else distinctive.

And what about meals at the park? One word: reservations. “Make reservations for dinner as soon as you know your dates,” Tennyson says. “Hot spots like Cinderella’s Castle book up very far in advance.”

Horrell adds you should consider booking those reservations at non-peak hours. For example, grab a breakfast reservation before the park’s opening time, or a dinner reservation at closing time. Also, take into account what your kids can’t or won’t eat—that will help narrow down the spots you will plan to go with your family.

Horrell highly recommends the website disneyfoodblog.com. It has a ton of great dining information.


If you’ve been to Disney before, you might notice a few changes because of the pandemic. For example, instead of the big parades, there are cavalcades—kind of like an unannounced mini-parade, with perhaps one float and a few characters or “cast members.” Socially distant character spotting opportunities are also unannounced, but the WDW Prep School website includes guides to their regular locations.

And of course, don’t forget to pack masks, and be prepared for temperature screenings at some locations.

Another change to keep in mind is that parks must be booked for specific days. Pre-COVID, you and your family could “park hop” from one to another in the course of the same day. Now, park hopping is available only when capacity permits.

For details on Disney World’s health and safety measures, head over to disneyworld.disney.go.com/experience-updates. You’ll find info on the precautions the park is taking and what you need to know before you arrive.

Happy (and safe!) travels.

Photo courtesy of Disney.