A First-Timers Guide to Planning a Walt Disney World Vacation: Part One



Updated January 2020

Living on the West Coast, Disneyland is our home park. It’s only a 2000 km drive (that’s 1242 miles for you Americans) or a 3 hr plane ride away. In 2016, our family (plus 1 family that is like family) decided to do Walt Disney World (WDW) together for the first time. That’s 19 people in case you’re counting. So we are by no means experts. But what we can offer is our experience in tackling WDW for beginners.

We knew we wanted to go, but truthfully, it seemed SO overwhelming. We also were on a budget, had five individual family units to consider, plus ages from 1 year to 60+. Being the planner that I am, I started obsessively pinning blog posts… and I’m sad to say that I still never did feel like I had a good grasp of it all until we finally got there and experienced it for ourselves. We hope this blog post helps make planning your first trip to WDW a little easier than we found it. We also had the great privilege of recording our story on the podcast “Detour to Neverland”. We talk a lot about our Disney World trip; you can listen to it here.

What Time of Year to Go

Planning a trip to Disney World. memory maker

Planning a trip to Disney World. There are a LOT of things to consider. My family didn’t want the summer because we felt it would be too hot. We couldn’t go Sep-Dec because of scheduling conflicts. Our preference was we wanted months that were low crowds(ish), but also hot enough to the enjoy the water parks. We finally landed on April. We went for 15 glorious days.

It seems like no matter what time of year you go to Florida, you can’t avoid the flash storms (ponchos are a MUST pack for Florida – buy them at the dollar store and save yourselves at least enough money for an extra dole whip or two). Summer is really hot and humid, plus it’s hurricane season. January and February can be quite cold.

For some people this may be a plus, but we wanted the sun! (I would have been fine with cold to be honest 😂.) If you’re sensitive to heat (like me) plan your trip around that. Christmas and Halloween Season is VERY busy. I think we landed on April because online we found a chart of high and low seasons and April was on the lower side for occupancy. Somehow we found two whole weeks that fit all of our schedules!

Booking the Trip

Update: Since writing this post, I have become a Travel Agent specializing in Disney and Universal! If you’d like me to do all of this leg work for you for FREE (free quote and NO booking fee or hidden costs), it will be the same cost for you whether you book with me or own your own, the difference is I can do ALL of these details for you, including booking, fast passes, dining, and more! Email me at: erica@enchanted-vacations.ca.

One tip is to watch flights constantly, and be ready to book when they go down in price. I really like google.ca/flights or trivago.ca (google.com/flights or trivago.com if you live in the USA) for tracking flights. You can enter your email, and will get emails when prices go up or down. We had 19 people booking at different times, so we were all a bit frantic trying to get online to book flights, but it ended up working well.

It was pretty funny when the flights we had our eyes on finally dipped down to an all-time low. Someone messaged the group to book ASAP. It was a mad dash but we all managed to get the flights we were hoping for at a steal. We ended up on two separate flights. The first group did an overnight Friday flight and the second group traveled on the Saturday.

Two more tips for booking: use an incognito window when checking flights, so they can’t track what you’re looking for and jack the prices. If you can arrange it, book your flights in the first three weeks of January. People typically can’t afford to book vacations after Christmas so you can often find seat sales and deals on hotels.

Where to Stay

Thankfully one of us from our group had been before, and he said we needed to stay at an actual Disney World Resort. When you stay at one of their hotels, you have free access to their Disney Bus System. This means that you can hop onto a bus in front of your hotel and go RIGHT to the gates of any of the 4 parks and 2 water parks, plus Disney Springs and any other Disney Resort. It takes all of the stress out of it. 

Planning a trip to Disney World. Hotel

The WDW resorts also have a complimentary shuttle to and from the airport as well as a luggage delivery service. We loved this! It made it so simple. You literally walk off the plane and to the shuttle area. After an overnight flight, we felt a little dazed and confused, so this was great. They will even mail luggage tags before you get there, so that you don’t need to collect your bags at the airport. You just need to make sure you put your tags on at home, drop them off at bag check, and say “See ya at the hotel, boys” (I don’t know why they’re boys… it just felt right). 

They also mail you your MagicBands ahead of time (USA only. If you are in Canada like us you pick them up at the front desk). You can even pick what colour you want. Plus you can put your name in it, so if you lose it (like our dad did at the water park) and someone finds it, that’s a good way to know you have the right one and avoid having to get a new one. This band is LIFE for Disney World. It has your park tickets, your shuttle pass (to and from the airport), your hotel key AND your credit card.

There are lots of hotels to consider… we chose the cheapest of the Value Resorts, “All Star Music”. 

The Value Resorts are:

  • Disney’s All-Star Movies Resort (newly renovated)
  • Disney’s All-Star Music Resort (family suites and some rooms renovated)
  • Disney’s All-Star Sports Resort 
  • Disney’s Art of Animation Resort
  • Disney’s Pop Century Resort (newly renovated)
  • The Campsites at Disney’s Fort Wilderness Resort

The Moderate Resorts are:

  • Disney’s Caribbean Beach Resort
  • Disney’s Coronado Springs Resort
  • Disney’s Port Orleans Resort – Riverside
  • Disney’s Port Orleans Resort – French Quarter
  • The Cabins at Disney’s Fort Wilderness Resort

The Deluxe Resorts are:

  • Disney’s Animal Kingdom Lodge
  • Disney’s Beach Club Resort
  • Disney’s BoardWalk Inn
  • Disney’s Contemporary Resort
  • Disney’s Grand Floridian Resort & Spa
  • Disney’s Polynesian Village Resort
  • Disney’s Wilderness Lodge
  • Disney’s Yacht Club Resort
  • Disney’s Riviera Resort (opened in December 2019)

The Deluxe Villas are:

  • Bay Lake Tower at Disney’s Contemporary Resort
  • Boulder Ridge Villas at Disney’s Wilderness Lodge
  • Copper Creek Villas & Cabins at Disney’s Wilderness Lodge
  • Disney’s Animal Kingdom Villas – Jambo House
  • Disney’s Animal Kingdom Villas – Kidani Village
  • Disney’s Beach Club Villas
  • Disney’s BoardWalk Villas
  • Disney’s Old Key West Resort
  • Disney’s Polynesian Villas & Bungalows
  • Disney’s Saratoga Springs Resort & Spa
  • The Villas at Disney’s Grand Floridian Resort & Spa

The All Star Music Resort was the cheapest of all the official hotels. (The three All-Star Resorts are in a row, connected). It had two really lovely pools, a fun playground, and a good sized cafeteria. It was within walking distance of McDonald’s, which was a plus (currently under renovation). One of the things I did NOT know was the scope of it. Just the All Star Music Resort itself was 7 or 8 standard hotel sized buildings. 

They all had really cool themes, there was a jazz section, a classical section, and a country section, and each building in those sections had a different instrument to tell them apart. When I was researching our trip, the size of the resorts did make me nervous. I had a ten month old at the time, and when I looked at a map of the resorts, I could tell that depending on where your room is located that it could take up to fifteen minutes to get from your room to the bus loop. 

Even though we called ahead as a group, we were all scattered across the resort. This worked out well for Danny, me, and our three girls… not so well for the other families. (NOTE: I’ve also since learned as a travel agent that you can put a “travel with” number on your reservation so this doesn’t happen. Another perk to booking direct with Disney.)

While we were there, it was THE World Cheer Competition. There were cheer teams from all over the world staying at the resort. Which is great for them. Sending a bunch of teenagers to Orlando with minimal supervision? Awesome. Running up and down the halls at 10:30 pm? Really fun if you’re a teenager. Large gathering spaces between the hotels for cheer meet ups and practices at all hours? Check. Respect for other people in the hotel? Zero.

 We happened to have rooms right in front of the only large grass area in the resort so we had teams practicing (as in their cheers) at all hours of the day and night. It started as early as 6 am (teams from all over the world) and went until late at night. Oh, and I can’t forget the night they were outside our room with a boombox (are those even a thing?????) and LOUD chanting.

I don’t have a problem with large groups of teenagers. They’re great. But we found that they had zero regard for other hotel guests. When you are trying to get a goodnight sleep before a full park day, it’s really hard to be kept awake so late. One night they even woke our kids up! We tried calling security (after 11:00 pm… we aren’t monsters), but found that they did not address the problem. However, a designated person from our group who has experience dealing with customer service brought our case to the management.

Hotel management was very receptive, and compensated our group fairly. So keep in mind when you’re booking that it is the cheapest option, which means that large groups (particularly high schools) will also be present. This wasn’t an issue for the families that were closer to the main building. Just the 3 of us in the furthest buildings. 

The rooms were spacious. The house keeping did a superb job. We made breakfast in our rooms everyday. There were classic Disney touches everywhere you looked. On the headboards, on the shampoo bottles, on the towels. This is what separated it from feeling like you were staying in a regular hotel to staying in a Disney Resort. 

If we could’ve stayed at a different hotel, I’m not sure we (the 5 of us) would have. We were able to do the entire 15 days with flights, hotel, tickets and food for $6500. Again, we are more prone to save money where we can, so we can go back as often as possible.  Would I like to stay at the Polynesian Resort? You bet. I’m just still stuck in the mindset that you spend so little time in the actual hotel that I’m not sure it’s worth it.

I think as a general rule, this is just a family principle. My family has a bigger budget than some of my sisters but I would still rather spend less on the hotel and more in other areas. Plus, for me, I’d rather be together than staying in separate resorts. I’m not sure that I would pick a different hotel either. The fact that we could walk to McDonald’s made a huge difference for us. 

Another perk to staying in the All-Star Resorts is they have 3 times the buses as the other resorts. You can take any of the All-Star buses back from the main parks, water parks or Disney Springs which makes getting around even easier. Last year my family (just the 4 of us) stayed at Disney’s Art of Animation Resort and this was one of the biggest things we noticed. It took us a lot longer to get anywhere.

Another down side is that only the All-Star Resorts and some of the more expensive resorts have buses that go directly to and from the water parks. When we were staying at Art of Animation, the bus took us to Animal Kingdom first, and then to Blizzard Beach. The way back was even worse. When you are wet and have had a long day at the water slides the last thing you want to do is get transferred multiple times. The second day we went to Blizzard Beach we ended up calling an Uber instead of waiting in the storm that had suddenly hit.

Art of Animation is the only other WDW Resort I have stayed in. We were in a Lion King Suite and it was amazing. There was a separate bedroom and washroom for my husband and I. Then the couch in the living room was a pull out. There was a small kitchenette and a table which pulled down into a bed as well. Plus there was a bathroom in the main living space that the kids used. Having a suite was a really nice bonus. They had messed up our booking so we got upgraded for free.

I wouldn’t stay in the Art of Animation unless it was in a family suite. The only non suite rooms are in the Ariel section and they are FAR from the main area. On the way back from our Disney Cruise (read more about that here ) we stayed for 2 nights. We were in late the first night and the kids just wanted to go to bed. We had to walk about 15 mins from the main area to our room. The rooms were great, but the distance is something to consider as it affects getting to the main pool, the main building where the cafeteria is, and the buses. This resort actually has the biggest pool out of any of the Disney Resorts and my kids really enjoyed it.

In case you need additional perks for staying on site, here’s the list of all of the reasons why you should:
– Free shuttle to and from the airport.
– Free transportation within the WDW resort.
– Book your FastPasses 60 days in advance, all at once, instead of one day at a time 30 days out. This may not seem like a big deal, but if you want any chance of getting a FastPass for the best rides (i.e., Flight of Passage, Slinky Dog Dash, Smuggler’s Run) this is a HUGE advantage. Don’t forget, if you book with me I’LL wake up at 4:00 am and work to get you all of those hard to get FastPasses!
– Free magical extras for booking a package with Disney (like free mini golf and coupons)!
– When you book a package direct with Disney (accommodations and tickets) you only have to pay a $200 USD fully refundable deposit, and you can pay off the rest of it whenever you want! This gives you the flexibility of cancelling and changing ANYTHING YOU WANT on the reservation up to 30 days before you travel! If there is a discount after you book (like there was for us recently with the Canadian Residents tickets) you can add them for no extra charge. If you book with a travel agent (like me!) they will automatically do that for you without you even having to ask!

– Free Magic Bands.
– Link your room key, your FastPasses and tickets, and even your credit card to your Magic Band and you are good to go!
– EMH (Extra Magic Hours) at the Park for onsite guests. This is PRIME attraction time, and even the characters will stay out for these extra hours. You only get this by staying onsite.

One more thing, if you are a family of 5 (and your kids are all older than 3, like my family now) there are limited options for you in regards to accommodations for staying together… unless you bring a grandparent and stick a kid in their room which works great! You canNOT just lie about how many are in your room, because you won’t get luggage tags, room on the shuttle, or FastPasses.

The options are the campsite (fits 10 people) or the suites at All Star Music (which lets be clear, are AMAZING and have a full size fridge, 2 bathrooms, and are newly renovated) and then the suites at Art of Animation that run a pretty penny. Unfortunately this does raise the cost up SUBSTANTIALLY so we do recommend bringing adults with you that can help with a standard room.

Booking Ahead

One MAJOR difference between Disneyland and WDW is that you have to book SO much ahead. We had some issues linking all of our tickets to each others app, but once we did, we talked at a family meeting about what rides to FastPass, and Elisia took care of that. 

Guys. Let me tell you the blood, sweat, and alarms that went into organizing our FastPass. As Canadians, we have the option of using Air Miles (a Canadian reward system attached to a major credit card) to buy park tickets. The nice thing too is that you are able to upgrade your tickets for the difference of what you have to what you want. One person can FastPass+ for the entire group. It only requires that you link together all of the passes. Now, because some of us had used Air Miles, it was slightly more complicated than if we had bought all of our tickets online. But never fear. It is doable, it is only a little more work.

So I linked all of the passes, including the ones from Air Miles. Once everyone is linked, you’re good to go. Just make sure that you are linked up with 65 days to go. You are able to FastPass+ 60 days in advance. On day t-minus 60, I was at the computer, ready to go. You can do it through the app or online by going to the FastPass+ section of the website. It was straightforward from there. You select a ride, and then select a time. I found the availability of passes to be excellent.

The only problem was that I had zero clue what the rides were, where they were, and how far apart they were from each other. However, I knew my group, and I knew I had their trust (just thinking about it makes me sweat a bit), so I pulled up a map of the park we were going to, and picked the top three rides that we wanted in each park. You do need to know at this point which park you are visiting on what days. I had been paying attention to ride times thanks to the app, so I knew which rides typically had longer line ups. Unlike Disneyland, Disney World has fewer rides per park, so there aren’t as many rides to choose from. It was our first time too, so I knew that there was no bad choice.

You can only have three FastPass+ per day. Once they are used, you may pick an available FastPass at a kiosk or through the app.

NOTE: Currently both Hollywood Studios and Epcot have FastPass Tiers… meaning that you can’t just FastPass three of the hottest attractions. Here are the current tiers (this is before Mickey & Minnie’s Runaway Railway opens in March 2020, and before they’ve allowed FastPass for Rise of the Resistance in Galaxy’s Edge).

Planning a trip to Disney World Fast Pass Tier


You can purchase the PhotoPass ahead of time for $169 USD. This is valid for your entire stay, and links to your entire group. This was a Christmas gift from our mother, which meant that all 19 of us had her PhotoPass linked to our MagicBands. Any photographer in the parks or Disney Springs would scan our bands and take our picture. We were then able to download the photos onto our personal computers.

As a large group, this made our lives significantly easier. No more awkwardly asking a stranger to take our photo! We were all able to use it individually as well, so we were each able to get a lot of personal family photos. This was invaluable! You also get really neat “magic shots”, where they interject little magical Disney pictures. As well as the photo studio at Disney Springs. So fun! NOTE: You will want to buy this in advance, because you can’t get pictures within 3 days of purchasing it!


One of the special things we did was book the “Beauty and the Beast” themed “Be Our Guest Restaurant” for one of our Magic Kingdom days. This was a highlight for everyone.  We “Disneybound-ed ” that day, and we booked an early dinner. It truly was special. You can book reservations as early as 180 days out. Some of the more elusive reservations sell out quickly, especially with big groups! The fact that we were able to get into Beauty and the Beast is a miracle. Don’t be too sad if you don’t see a reservation that you want right away, though… be diligent to check back to the website as often as you can, sometimes people cancel and things open up.

planning a trip to Disney World. ADR

Early Mornings / Which Day To Do Which Park

When going over which days to do what, we factored in some things. We chose not to do Park Hopper tickets because we had strollers (and babies that are not easy to quickly pack up and hop on to a bus with) and eight days to experience the parks. Because we didn’t park hop, my family only visited Epcot once, which was sad.

We also considered park hours, special events and EMH (Extra Magic Hour) before and after the park is open for off site guests. Some people will tell you to avoid those days because the parks are busier. Because we are morning people, we choose to take advantage of that extra hour in the morning. (Though that 3 hour time change made this a little more difficult as waking up at 7 am in Florida was 4 am our time.)

The other thing was we looked and saw there was a marathon in the Magic Kingdom on our first day in the parks, so we avoided it. We found this to be really tricky for WDW vs Disneyland. For Disneyland we make a general schedule of what days we’d like to do what park but for the most part it’s flexible. For Disney World, you have to make reservations and book your FastPass far in advance or you miss out. 

Water Parks and More

Since we went in 2016, this has changed. When we went, we were able to select a “plus” option. It does cost extra, but with that you can enjoy 1 day in any of the “plus” options for every day that you purchased a park ticket. So if you have an 8 day park ticket, when you select the “plus” option you also get up to 8 days in any of these options:

  • Disney’s Blizzard Beach Water Park
  • Disney’s Typhoon Lagoon Water Park
  • ESPN Wide World of Sports Complex
  • Disney’s Oak Trail Golf Course
  • Disney’s Fantasia Gardens Miniature Golf Course
  • Disney’s Winter Summerland Miniature Golf Course

WDW has since moved to a new ticket system. Ticket prices now depend on the time of year you go. Prices are cheapest during January and February. You must know your dates in order to purchase tickets, or you have to pay a little extra for flexibility for your dates (you can change your first date on the app if needed, but will have to pay the difference if there is one).

 If you would like to use the “and more” option, after you have selected your date, number of dates, and number of tickets, you are able to “customize” your ticket type. You must upgrade to the “Park Hopper Plus” option to take advantage of the additional facilities. The previous ticket system charged $68 USD for the “and more” option. Now this option is $100. So really, you’re getting a Park Hopper for only $32 more, which isn’t the worst.

You can choose to do them on the same day as a Park day. We chose to do them on off days. We did a full day at Blizzard Beach, and a full day at Typhoon Lagoon.  We liked Blizzard so much we ended up using 4 of our 8 tickets for that, then 1 for the mini golf, and 1 for Typhoon, leaving 2 technically “on the table”. It was so nice having them for our days off. We would ask the kids if they wanted to stay at the hotel and play at the pool or go to the water parks. Easy answer for them!


There were 3 families that did an overnight flight: my family with kids age 5 and 8, Elisia’s family (11 month old baby), and our friends who also had an 11 month old. We just wanted to get there! Plus, it was the only direct flight. So we decided to brave the overnight. I can’t speak for my fellow travelers but this worked really well for my family. We brought a neck pillow, a small blanket and eye masks so they would sleep.

Our flight left at 11:30 pm our time so I knew they would be tired already. We got into our seats, I got them situated and said it’s time to go to sleep…. and they did!!! I was so shocked. I didn’t sleep very much on that flight. It was about 7 hrs long. My kids slept virtually the whole flight, I slept maybe half of that in and out.

 I had my babe on my lap all night. I thought he would fall asleep while we were going through airport security, but he did not. Then I thought he would fall asleep while waiting to board… but he did not. THEN I thought “surely he will sleep on the plane”. Once we had taken off I strapped him into my Ergo wrap, so that I could fall asleep without worrying about dropping him. He finally fell asleep during take off, and only woke up in the last hour of the seven hour flight. So I did not sleep all night. But it was nice getting there and having the entire day to explore the new world. 

One plus was it made transitioning into a +3 hr time change seamless for us. We kept them up all of the next day and they were ready for bed at 7 pm that night (which would have been 4 pm our time regularly). Though we felt a bit like the zombie apocalypse all day, it was worth it in my books. You just have to go in with a game plan. Which we had, then proceeded to not follow. BAD MOVE.

I knew that we would be starving in the morning after flying all night. So we had talked about the fact that we needed to eat after we got off the plane. We did in fact go to Starbucks for some much-needed caffeine, but we did not purchase any food. We had breakfast for the kids in the form of food packs, so they were happy. But I just didn’t want to pay $15 for breakfast from Starbucks that wasn’t going to fill me. So off we went to the hotel. The shuttle made it a breeze, and it felt like we blinked and voila, we were at our hotel.

Our rooms weren’t ready (since it was like 9 am in the morning), so we decided to venture out to Disney Springs. In reality, we should’ve headed to the cafeteria, or walked over to McDonald’s (now that we know it’s so close). If I was to do this again, I would pack PB and J sandwiches to have in the morning. But at that point it was like, let’s just get to where there are a lot of food choices, and go from there.

We had pre-picked a restaurant, because we knew we were going to be starving, but once we saw it we realized that it was more pub-ish then family-friendly. So, we wandered and wandered trying to find somewhere to eat. We finally picked a restaurant after wandering for over an hour, and could barely enjoy our food because it took forever, and we were starving. So don’t be like us. Eat. Buy the stupid Starbucks breakfast sandwich, or pack the breakfast cookies. But just eat. 

My parents, Danielle and Levi, and our family of 5 opted to fly the next morning.  There were 2-3 transfers, and it was a LOOOOOOONG day.  But because we were spending SO much time at the parks, we really didn’t mind it.  We couldn’t leave on Friday night because of my husband’s job, and that being said, I’m not convinced I would’ve wanted an overnight flight with a 3 year old, a 6 year old and a 9 year old.

Thinking about it now, I cannot believe that we pulled it off. We definitely learned a lot along the way, and can’t wait to share more with you about how to successfully “do” Disney World.

Check out our next post, A First Timer’s Guide to Planning a WDW Vacation Part Two, here.

Have a magical day!
Erica, Heidi, Elisia and Danielle

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