What Disney Wants You To Do:
Keeping in mind what Disney as a company wants guests to do can help to understand why things are the way they are.
Disney wants you to go to Walt Disney World and have an amazing experience and make memories that last a lifetime. To accomplish this, they have extraordinary options which are designed to ensure Disney shapes your experience and no one else. Disney wants you to spend a long time at Disney World and only Disney World while you visit. You can buy tickets which will be valid for up to 10 days and the longer you stay, the less expensive each day is. The longer you stay at one of their resorts, the less expensive each day is. They do not want you to have a car on site. If you keep some of these things in mind, you will understand why it may be frustrating if you plan a shorter trip, for example, or if you don't intend to spend all of your time in the Disney Bubble.
The sweet spot for booking flights at the cheapest price is six weeks from departure if flying in the US. I use flights.google.com to review flights and narrow down dates. Flying in the middle of the week will usually be less expensive than the ends. Make sure to account for carry on luggage when searching, since Spirit and Frontier will usually be less expensive, but not necessarily when you add up bag fees. If you stay at a Disney resort and you check a bag, depending on your airline, you may be able to use the bag delivery service, which whisks your bags right from the airport to your resort so you can get to the parks as quickly as possible. Keep in mind that it may take 8 hours for your luggage to arrive in your room if you do this, since your bags don't go on the same bus as you do, but is picked up on a truck and delivered in groups. If your bags are needed, Luggage Services may have them waiting near the main entrance to your resort.
You can use Hotwire to book a Disney World Resort at a Hot Rate, if available. The trick is to filter your search. Narrow the location to just Bay Lake and choose Airport Transportation as an amenity.
A quick note about Disney Resorts: They are all amazing properties with all amazing staff. There are three main categories of resorts, value, moderate and deluxe. There are also deluxe villas which are mainly Disney Vacation Club resorts, available as a timeshare option. I have only stayed at the value resorts, which has been amazing, but the more expensive resorts will be less crowded, maintenance items, like worn paint and carpet are replaced faster and usually the on site restaurants and bars have fancier food.
Disney will usually offer hotel discounts on their site as well, usually about 10 to 20 percent off or offer things like free meals. Slower times of the year when this happens are at the end of the summer and into September, the first half of December, January and February until Spring Break happens and the end of May.
There are a ton of offsite hotel and resort options in the Orlando area. Some offer transportation to Disney World and some do not, so check if it is important to you. By staying onsite and using Disney Transportation, you can usually nap in the afternoon and go back to a park for the evening. That becomes more challenging if you stay offsite.
The cheapest options for Disney tickets limit you to only visit one park per day. For example, as of December 2019, a single day one park ticket is as cheap as $109, but if you want to visit more than one park, add $60 for a single day ticket. For a 10 day ticket, it can be as cheap as $47 per day and you can add park hopper for $80. Basically, it is very inexpensive to add additional days if you are staying longer than 4 days. Pricing is variable as well, based on date. Your 10 day ticket may be $470 or $690, depending on the time of year. You also don't have to visit on consecutive days. Disney knows how intense visiting parks is. It is a sensory overload. Resorts are much quieter and relaxing, so they know people should take breaks by having resort days.
Annual passes are also an option if you may plan multiple visits in a year, say two or more four day visits. I have liked this option, because I like shorter trips. I only visited once before without my parents, and it was stressful trying to cram in four parks in two days, but did so to try to get the most out of the expensive tickets I had bought. I have visited 22 days in the last year and there is still plenty I haven't done yet, so you may not experience everything you'd like to either.
MyDisneyExperience and MagicBands
If you stay at a Disney Resort, one of the benefits you get are MagicBands. These will serve as park tickets, your room key and, with a PIN, allow you to purchase things in the parks. You can even upgrade to a fancier design ahead of time. MyDisneyExperience is the website and app you will use to book your dining reservations and FassPass+ selections. Dining can be booked up to 180 days in advance if you stay at a resort and FastPass+ selections can be made up to 60 days in advance.
If all of that planning is stressing you out, then don't worry about it. FastPass+ isn't required, but you may be waiting an hour or two to ride one ride, so keep that in mind. Once you have MyDisneyExperience on your phone, you can also see wait times for rides before you go. While it will be different when you visit, you can get a sense of how busy your planned rides are.
FastPass+ selections do change all the time, since people modify at will, so always keep an eye, even the day of, on a ride you want, since you may luck out and get a FastPass+.
Dining reservations can be similar. Like rides, there are very popular restaurants. Usually the most popular options are for character experiences, but the food options are all great at Disney World.
What to Wear
Florida has a lot of rain, like all the time. It is mostly warm, but some times of the year is pretty cold in the morning and roasting in the afternoon, then cold again. You may need to dress in layers, plan a few outfits for different parts of the day and have a raincoat or poncho handy. Rains are super quick most of the time, like minutes long and other times, huge downpours, but Disney is not in control of the weather. Also, wear sunscreen.
One thing I didn't realize before this year, is how coordinated families get with shirts. Disney even sells custom family shirts for your trip. You'll see lots of custom shirts with funny sayings and you may feel left out, so plan ahead to coordinate or show off your own favorite characters.
At the Parks
Getting into the parks is pretty quick. All have security with metal detectors and bag checks. Turnstiles are all fast, since you just need your MagicBand and fingerprint.
You may be overwhelmed when entering a park, since there are so many people, especially at Magic Kingdom. There are areas off to the side with benches and quiet corners if you need a moment.
Water is available everywhere. Every quick service restaurant will give you a cup of ice water on request. Keep hydrated.
Take breaks when you need to. If you are traveling with a family, take your time if you need to. Often times, people get stressed because their kid is tired, but they have a FastPass+ selection which is expiring soon and their kid just wants to sleep for a bit. Disney is extraordinarily accommodating and if you go later, it usually isn't a problem. Since so many people visit Disney World, they have seen everything and want you to be happy.
Don't be afraid to change your plans. Maybe you need to cancel a dining reservation because someone isn't feeling well. Please speak to a Guest Relations person and they will take care of you rather than forcing someone into a plan you may have made months ago.
You can't and won't see everything. There are special shows which only happen during certain times. There are characters which only appear during certain times and in certain places. You can plan some of this, but it is fun to randomly run into Snow White. There is also so much to see which have nothing to do with rides. If you have a really young child, there are characters to meet all over, ducks walking around which aren't even named Donald, quiet corners can be found around to relax, get splashed with water if needed or just sit and color.
You can bring food and drinks to the parks, even small coolers. There are dining plans available, but keep in mind you may be better off if you don't eat three times a day while you are at Disney World. You will probably be pumped with adrenaline, which may impact your appetite. Expect to pay about 70 percent more for your meals than you would at home, so not quiet double, but close. The food I've had has all been very good and have had no complaints.
There are huge stores in Disney World and the selection of merchandise is constantly changing a overwhelming. Ship it home if you want to load up, or plan ahead to have space in luggage. You can even use the MyDisneyExperience app to locate merchandise you may see someone wearing. Disney even has two Character Warehouse stores in Orlando at outlet malls if you are looking for a deal.
There are some really cool things you can only get at the Disney Parks, think exclusive designs from luxury brands. If you may be tempted by such things, budget with that in mind.
Be open to changing plans
You don't need to buy everything
Take breaks as you need
Set your expectations