Okay so let me prelude this with a quick backstory summary. My family and I are Disney crazy. While I was growing up we went to Disney twice a year. I was probably the most Disney-versed kid. It made sense that when I got to university, we heard about the International College Program, where kids from around the world go and spend 3 months working at Disney... Talk about a dream come true for a nerd like me! It was an incredibly hard 3 months for basically no pay, but I strongly suggest it for everyone's kids if you can get them there. It is a great experience and a lesson in hard work.
What we learned working there:
On top of this, I met my now husband there, as he did the same program and got put on the same ride as me (Jungle Cruise). 
So, I have a little bit of experience, but I wouldn't say I'm the world traveler. I'll try to cover what I can from my perspective on how to save at Disney (Florida) for my future trips.
When
-Travel during Disney's value season. This info is on the WDW website, but a basic summary can be seen in the attached picture for example (this was last year). This is when the park will be the quietest (still crazy busy though) and the cheapest. It's easier to get fast passes for the rides you want and bookings for dinner too. Plus no waiting half your day for one ride.
Where
- this can be up for debate depending on circumstances, but for the most part, staying on Disney property is expensive. If you can stay off-property you can save a ton, enough to rent a car for the duration. Typically, I would suggest staying off property (but still close) and renting a car, which allows you to spend your money for meals at Walmart, buffets and cheap places instead of every meal sprinkled with Pixie Dust.
- The benefit to staying on Disney property is the transportation aspect - IF you are only going to be doing Disney. While in Florida you might want to see Universal Studios or SeaWorld or Clearwater beach. These shuttles aren't available from your front steps at the Grand Floridian! Again having a rental car helps in this aspect.
- house rental. AirBNB or general websites allow you to rent a whole house for the duration of your stay instead of staying at a hotel. I've done this with the family and let me tell you how nice it is to have a kitchen! A little bit of research is needed here to find a place close to all the amenities you want, with the inclusions you want (like is there a community pool?). You'll have to rent a car again, but this is an awesome option if you have a large group or are planning to stay longer than a few days in Florida.
- another cool option is camping at Disneys Fort Wilderness campground. I would suggest NOT doing a tent, since it's really hot and rainy in Florida, but you could rent a trailer/motor home and park it on a campsite for a little less than a hotel room. The campground has a lot of cool fun free stuff (like each hotel has), but biking/walking around is the most fun. Whenever my family stayed, we did up the whole front area with welcome signs (everyone does actually).
- another where to consider is what kind of stay you'd like. Totally fancy? Try the Grand Floridian or the Swan and Dolphin. Cheap as possible? You'll look at the value resorts like Art of Animation or Pop Century. I personally like the idea of staying at any of the resorts that are right on the water across from Magic Kingdom as the monorail and boats can get you to and from major points of interest quickly (I'm not a big fan of busses due to car sickness). Plus, these resorts can get extra cool freebies I'll describe below. Our favourite new hotel has been Port Orleans.. Cheaper, really nice, walking distance to Downtown Disney and all the transportation busses
- When and where can also be dictated if you look into becoming a Disney Vacation Club (DVC) member, as they have priority rules and such plus must book before 1 year stipulations. This is similar to a timeshare option, where you buy and maintain points for stays at Disney World, Disney Adventures, not-too-Disney resorts and locations and more. It gives you discounts around Disney for food and shopping, but make sure you do your research and homework before jumping into this (especially with the US dollar the way it is) as it almost works out to a second mortgage
Tickets
- this is another one that will take a little bit of number crunching, depending on what you want. You can get a pass from a one day, one park admission up to an annual pass with unlimited ins and outs and free parking included.
NOTES: Watch expiry dates (so if you're coming back the same year do an annual, if you're not coming back for a couple years, do the park days and use them up or add the "no expiry" option). Magic Kingdom park tickets are more expensive than the other three parks' tickets. One park admission = literally one park, and if you wanted to do two parks in the same day then this would count as 2 days admissions. You can add a "park hopper" option to any park pass (a one days adds $160, a 10 day adds $470) which allows you to do as many parks in one day as you want, while only charging you one day admission.
- basically, I would do the math before jumping into buying the ticket the morning of. There is a lot to do at every park, and Epcot in itself in my opinion could be counted as two parks (the World Showcase of countries can take a day to get around alone). It can be totally exhausting to try and do one full park in one day (you can't possibly meet every character or do every ride in each park in 1 day, plus what if day 1 everyone gets horribly sunburnt and you still have three full park days planned?). This is an easy decision if you are not going to be at Disney long (3-4 days), but if your math starts adding up to being close to $700 per person, I would suggest jumping to the annual pass for the added perks and options.
- the annual pass also gets you discounts around Disney for meals and merchandise, kinda like a DVC member. You can save on rooms and excursions too by mentioning this.
- I really like the annual pass for the freedom it allows - maybe you want to see the animals in the morning at Animal Kingdom, have lunch at Prime Time Cafe in Hollywood Studios, then catch the Wishes fireworks at the Magic Kingdom. Then maybe the next day you've booked a Segway Tour at Epcot, but would rather spend the day after at Magic Kingdom. An annual pass allows this freedom, while those two days could either count as 5 days admission or 2 park hoppers day admissions otherwise.
Free Entertainment
Okay so you've finally picked the where and when and you are ready. Besides the have-tos in the parks, I'll try to let you know about free stuff outside of the parks
- the Electical Water Pagent. This is quick and cheesy but I like it. It happens out front of a few of the beach resorts around the Magic Kingdom area, just before the Wishes Fireworks go off. Try Polynesian Beach, Grand Floridian Beach, or Fort Wilderness Beach. We like the Polynesian Beach because we grab a couple of amazing Dole Whips to eat while watching the show.
- beachside movies. A bunch of resorts will set up a screen and play Disney movies on it, sometimes around a campfire like at Fort Wilderness. Bring a blankie and watch for free! Polynesian, the Beach Club and Fort Wilderness do for sure, the others might too
- Fort Wilderness has horses! Cinderellas ponies are all stabled here, and you can wander and see them (when allowed). The beautiful carriage horses are usually down by the dock too, and you can sometimes get someone to take your photo with these guys.
- boat rides. I think everyone loves a little ferry ride, and I love watching little kids get excited over this freebie. You can take a long ferry ride around the Magic Kingdom area, which goes between the hotels and stops at a leisurely pace. When you take the full ride, you could also get a little mini tour from the captain who can point out wildlife and the old River Country water park as it passes. There is also a ferry ride over at Disney Springs (Downtown Disney) that goes between a few resorts. Make sure you hop on the ferry that takes you over the water bridge, while cars go underneath you!
- wildlife! This might be the tourist in me talking, but you can see wildlife all sorts of places. Beaches are the best, and egrets are quite interesting to watch, but I have a favorite place... Try a walk around Fort Wilderness, where we always see deer, armadillos, bunnies, once a gator and all types of birds. If you wanted a little more exotic, Animal Kingdom is worth a full day's adventures with all their hidden animal treks and shows.
- aren't monorails cool? Seriously, ride this around and get a birds eye view of hotels and of Bay Lake. Challenge family members to memorize the announcers "pour favour.." line too. This also allows for Hotel jumping which is very cool to go and wander, as each hotel is themed differently
- maybe this doesn't count but you can ask for ice water or a cup of ice at vendors in the park for free
- pin trading! Buy a starter pack of the cheapest pins you can (usually 4 for $9.99) and then pin trade with anyone you see wearing a lanyard of pins. Even some stores will have a "pin trading" collection if you ask. Trade up and up for a great few souvenirs, and have some fun along the way
- Downtown Disney has a few shops that lets the kiddies (or the kiddies at heart) play. Try Lego building or Mr Potato Head creating
This last freebie is worth a separate bullet point all its own:
Hidden Mickeys
These refer to hidden secrets and gems all over Walt Disney World. Virtually every hotel and theme park will have a secret hidden item. A lot of the time they are actual Mickey heads, but sometimes they are hidden items like the wedding ring at Haunted Mansion or a mistake like the 5 legged goat at the Contemporary resort. Do buy one of the Hidden Mickey books (off property before you go on your trip) and after you've done some of the parks, look up what hidden Mickeys are to be found at the hotels and such
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