My answer to this is usually, "um, I just decided that I need a trip, so, like, let's look at the calendar and see when airline prices dip?" But not everyone has that flexibility. Here are some things to think about:

I can't take my kids out of school!

Totally understandable. But know that crowd levels will probably be busier over any school breaks, peaking in the week between Christmas and New Years, Spring Break, summer months, and Fall break.

My elderly parents have trouble with heat and humidity.

I'm 37, and I have trouble with heat and humidity! January and February are the coolest months, and checking out an Orlando monthly temperature average if you or people in your party have adverse reactions to heat and humidity isn't a bad idea.

I'm allergic to crowds.

Sorry dude, there will always be crowds at Walt Disney World. But if you're looking for smaller crowds, looking up Walt Disney World's tiered pricing system, which began in March 2016, is a really great way to prepare yourself for crowds. Is it value season? LOWER CROWDS. Many Walt Disney World travel sites have their own crowd calendar, which might be worth a look. That is, if when you Google "WDW Crowd Calendar" and look through the different ones available, you'll notice that they all differ from one another.

I don't want Ichabod in my Cinderella Castle picture!

Ichabod is the affectionate name for the construction crane that hovers like an annoying swarm of mosquitos over Cinderella Castle from mid-January into March, late August into September, and late October into November. In other words, the lowest crowd times, as Walt Disney World prepares for the next season of decorations. I consider Icahbod a member of the Disney family at this point, but the Disney photographers are really good about getting angles that don't include him (unless you ask for it, I suppose?). And no, there's no way for the cast members to take him down each day and put him back up at night.

When is the best time to go, you ask? I say: WHENEVER YOU CAN. But balancing the above factors when making travel dates will prepare you for your time at Walt Disney World.

That is a question best answered by you. Let me explain.

Ticket Prices

So. Many. Options. Single day tickets for guests age 10 and up begin at $97.00 during the value season for Epcot, Animal Kingdom, or Hollywood Studios, and go up to $124.00 during peak season for Magic Kingdom. The cost per day decreases on multi-day tickets, good for fourteen days from first use. For example, a three-day ticket for guests 10 and up is $290, while a ten-day ticket is $400.00

If you will be at Disney more than one day, Five Star Mouse highly suggests investing in the Park Hopper add-on, which allows you to visit more than one park on the same day. Park Hopper is an additional $69 per ticket regardless of how many days you are spending in the parks, and it opens up the parks to you in a way that being limited to one park per day does not. I personally see that $69.00 as an assumed cost, and don't do Walt Disney World without it.

For an additional $26.00 (beyond Park Hopper), you can add the Water Parks and More option, which also gives you access to both Disney Water Parks and other recreation choices.

More Add-Ons!

Over the past few years, Walt Disney World has added a number of ticketed events, ranging from dessert parties during fireworks, Early Morning Magic (an extra hour in Fantasyland before park open, plus breakfast), the popular Mickey's Not So Scary Halloween Party and Mickey's Very Merry Christmas Party, a multitude of backstage tours, and so much else. Available events are listed under the Special Events page on the Disney World website. Check it out and decide what events, if any, are best for you.

Special Tickets

If you purchase tickets through a third-party, decide to purchase an annual pass, are a member of the military, are a Florida resident, are attending a conference, own a dog from the same littler as Uncle Walt's third cousin's great-grandnephew twice removed (okay, not really that one), tickets could be available at a lesser cost.

Where You Stay

The on-property resorts range from reasonable priced to dear-fairygodmother, as do off-property resorts. See the Resorts page for more information.

What You Eat

Food options also run the gammut from expected to Dionesyian proportions of gluttony, with pricing to match. See the Dining page for more information.

No matter what you decide, know this: I have experienced exceptional levels of the fabled Disney service at all budget levels of a vacation. It really is what works best for you.

The easy answer? NOW! Mainly because it's fun. But there are some things you need to think about well in advance.

Resort Reservations

If you want to stay in one of the on-property resorts, a room-only reservation can be made 499 days in advance by calling Disney Reservations (407)WDISNEY. This is especially recommended if booking during a very busy season (i.e. 4th of July or the week between Christmas and New Years), or if there is a specific resort or room type that you would like.

Is it necessary? I don't think so, particularly if you're flexible.

If you want to book a package,which normally includes room, theme park tickets, and possibly the Disney Dining Plan (DDP), those are normally released sometime in the summer for the following year, and can be reserved on the phone or online.

My take? I've only booked one trip more than four months out, and I've always been happy with my resort room options. Because I will be at Walt Disney World.

Dining Reservations

Advanced Dining Reservations (ADRs) can be made 180 days in advance, and if you're staying on-property you can reserve your check-in date plust ten additional days after that (180+10). Because Disney's resort restaurants are open to anyone and you don't need to have a room reservation or purchased tickets to make dining reservations, it is best to do these are far in advance as possible, especially if you're interested in hard-to-get reservations at Character Meals or Disney's Signature restaurants.

Dining resrvations can be made on the phone or online, and require a credit card number. With the exception of a few pre-paid locations, the card is only charged if you fail to cancel within 24 hours of the reservation.

My take? I'm pretty open about where I eat, but when I use the DDP I do like to have everything lined up. You can learn more about the DDP and various restaurants on the Dining page.

FastPass+

FastPass+ (FP+) reservations can be made 60 days in advance of check-in if you are staying on-property, or 30 days if you are staying off-property. More information on FP+ can be found on the Understanding MyMagic+ page.

I Think I'm Going To Tell My Kids On The Way To The Airport.

My take? I think your vacation will be much happier involving the entire family in the planning, especially if it's your kids' first trip. Walt Disney World is gigantic and overwhelming, and involving the kids in the planning allows them to tell you what they're most excited about (and their answers might surprise you!), and gives them concrete things to look forward to doing. It also take the pressure off of you trying to create the MOST. MAGICAL. TRIP. EVER. and designing an itinerary that might no go as planned. And don't worry - the first time your family walks underneath the train station at Magic Kingdom and sees Cinderella Castle for the first time will be just as magical whether they know at the very beginning of the planning process or not until you pulled into the parking lot.

The best idea I've ever seen is to have each person in your traveling party create a top ten for each park, or overall, including attractions, restaurants, character meet and greets, and anything else Walt Disney World has to offer, and then sit down and compile those lists together to get a good idea of what you're going to do on your vacation! It's probaby best to have this completed before your FP+ reservation window opens.

So When Do I Make Day-To-Day, Hour-To-Hour, Minute-To-Minute Itinerary?

My simple answer: you don't. IF you have your dining, FP+, and any other bookings completed, that will give you a few touchpoints throughout the vacation that are set, and the rest is up to you and your family!

If you are a bit more type-A than this (and that is totally cool), Five Star Mouse is happy to help you plan your days. Just email me, and we'll chat!