Planning my First Trip to WDW, A Dream Come True Indeed.


Earning My Ears
Nov 27, 2019
Hey there everyone;

I am rather new to the Boards here as this is my first post but I feel like I just need to put this out there because the build up of excitement is starting to drive me a little crazy. So where do I begin? Well the beginning is overrated but I will get there.
Here is where I am at now. It has been 7 months now since my friends surprised me by saying they wanted me to accompany them to WDW and that they are specifically planning on making the Road Trip from Toronto, Ontario, Canada. As of typing this out there will be four of us heading down and three of us can drive so their plan was to long haul the drive and stop only for food, and gas until we reached the resort. As soon as they mentioned this trip to me I removed my walls around 'planning a Disney Vacation' that I had put into place as a child. We simply could never afford to make a trip like that so rather than get my hopes up I simply just closed my eyes to Disney Parks. Now that those walls are down I began my research and planning. I have written pages upon pages of notes about this adventure I was preparing to undertake. There are some hurdles I am having to try and find my way over.

First we are a group of 4 Adults and two of us happen to be a engaged couple (not me) so the basic room while it could work for us I kind of want the couple to have a little more privacy. This option seemed easiest to solve by settling on a Family Suite at All-Star Music Resort for 6 nights. Not my resort of choice but this is the most affordable way for us to get the accommodations that we would need as getting two separate adjoining rooms seems like it would come out being more expensive. I am the major decider on the fact that I want to stay on Property. I am the one in the group who does not drive and if my friends wanted to stay at the resort and relax, if we stay on property it just makes it so easy for me to get around and visit the parks to my hearts content.

The other hurdle I am dealing with is that everyone seems content with not planning anything at all for the trip and leaving that in my hands. So great you are letting the guy who has never left the province he was born in let alone visited the WDW parks take care of the planning? Ha... Yeah that's probably not the best choice, especially when it comes to trying to figure out ADR's. Now I am not going crazy here, I am not planning things down to the minute. I do love the idea of a free-form Disney vacation with no real strict plans. The only thing I am trying to plan out is 1 meal every night of our stay. So yeah fighting with myself about "is that too much to expect for the vacation?". I have tried to talk to my friends about this and I get three different versions of "Dude we are not even going until November 2020, it's way too early to be thinking about any of that". They just don't know.

I love the planning and learning everything I can about the Vacation because I know one thing is guaranteed to happen. When I get there I'm going to be overwhelmed I know I will be. I have been a Disney fan since I was 5 years old and that love hasn't gone away. All the stories of people crying when they step foot onto main street and see that Castle for the first time... Yeah that's going to be me I know it.

Thanks for letting me get this out there. I needed to talk about it somehow because if my co-workers hear the words "Disney" out of my mouth again I am going to have things thrown at me.


DIS Veteran
Aug 16, 2013
First congrats!

Second doing two rooms at a value might be cheaper than the suites. That way the happy couple could have their own room and you’d still have two beds in the other room plus you’d still get two bathrooms. It might even work out cheaper to upgrade a little and look at Pop Century which would give you the added bonus of the Skyliner. Just something to consider.

After that it’s really personal preference. I’m not a huge fan of table service options but since it’s your first trip a character meal would give you a fun experience. Breakfast meals are your cheapest character buffets. Garden Grill in Epcot is nice because it’s all you can eat but you don’t have to worry about little hands touching everything because the food is brought to the table.

Don’t discount the quick service options. It’s more than your standard amusement park food and for the most part it is the more inexpensive option. We are huge fans of quick service because it takes away less park time.

FP+ once again is personal preference. Do more research on all the rides and the whole process. Basically pick your parks and choose early FP+.

I am not a morning person but at Disney I am because you get more done if you go early.

once again have a wonderful trip.


Jun 14, 2019
Fellow Canadian here, taking our first family trip to WDW next month! We're driving from Ontario as well, but we're not planning on driving straight. It will mostly be my husband driving, though I'm always willing to. We have a five-year-old son as well.

My husband wasn't really involved in the planning, and he was a bit surprised about how much planning it takes. I had to get up on Christmas morning to make our FastPass selections, and then yesterday, Disney decided to throw a new wrench into the mix at Hollywood Studios by releasing FPs for Millenium Falcon and rearranging all the tiers -- I had to think quick while I was at my son's gymnastics class, lol. But... for the most part, planning has been fun! If nobody else wants to take part in it, then they'll just have to deal with whatever plans you make, lol.

My only tip for ADRs is to go ahead and book the same restaurant on different days if you're not sure which day you're going to a park. You can always cancel it later. It's very hard to decide which park you want to go to on which day six months in advance. I tried, but only 2/5 days ended up staying the same by the 60-day mark. My only other tip would be to watch all of the Disney Food Blog videos on YouTube. I was bedridden for a while, and that's how I learned almost everything about planning, not just food.

You could definitely consider a separate room for the engaged couple. I haven't looked at the different prices, but it might be worth it just to have the extra privacy and probably extra bathroom, lol. You could also consider a Disney Springs hotel, which might have better amenities for hanging out at the hotel all day long if that's something your friends want to do, plus there is lots of entertainment right in Disney Springs. Those hotels have pretty much the same benefits as a Disney resort, though the transportation options aren't as extensive, but they do still have buses. I seriously considered staying there, but the main reason we decided to stay at Pop Century was just so we could purchase everything as a package. We did the Quick Service Dining Plan.

Have so much fun!!!


Earning My Ears
Nov 27, 2019
The main reason I am stressing out over the plans so much is not because I want the vacation to be perfect. That is a pipe dream and I know it. I am planning a huge surprise for my friends. We all of us have had a rough 5 years between family and personal trials and tribulations and that's why we are all taking the vacation at this time. As I've described it to them "Distance and Borders mean nothing when we hold Magic in our hearts ... We are here to recharge on Pixie Dust" (The ladies are American and the Guys are Canadian so sadly we spend a lot of time apart from each other). With all that we have gone through I am aiming to treat us all to the Deluxe Dining Plan. Since they are doing the driving and covering the costs of the driving I was going to cover the costs of the DDP as my gift to each of them. I know just how insane the Deluxe plan is (Huge Fan of DFB and have their guide books on my phone for study while on break) but the reasons for going that route are to not have to worry during the trip if we accidentally over spend on souvenirs (couple of us are huge Star Wars fans so yeah.... Lightsabers) and going with the DDP means we don't have to worry about accidentally spending the money we had set aside for meals. It also makes it easier for us to experience not only 1 or 2 signature dining locations during the week but also gives us ... well to be honest here it gives me the best option for experiencing all of the Character Dining that I want to.

We are settling on getting the Park Hopper tickets as we felt it lends itself better to taking things as they come and not being locked into a set schedule. Yeah might not be the best value but we want the options to not be locked into a park if we get there and just feel like we would rather be somewhere else. Slightly crazy I know but it keeps things open for us. Personally I know I am going to be bouncing through Hollywood Studios multiple days during the vacation and that's just because I want to get back to Galaxy Edge.

It gets tricky when it comes to Fast Passes. I'm not one for rides really. There are a few that I really want to try like Splash Mountain even though that main drop is scaring me. Heights and I just don't get a long all that well. So there is a plan in my mind (and on spreadsheets I've created with a timeline for the week. Yes I really went planing crazy) to aim for 4 rides a day. That's really it. I am not planning my friends FastPasses as we don't know if we are going to be always together as a group or if we are going to split off and meet up and multiple points over each day.

Something tells me that I am going to fall in love with this place more than I could imagine. I see myself doing the Annual Pass dilemma very strongly and that would just give me that little kick in the pants to try out flying. I mean Toronto to Orlando is only 3 hours away. I can handle the stress of a flight for a little longer than a Star Wars Film. That should be doable. I think.

Thanks for your feedback and your tips about the plans. It's really good to talk with other Disney fans about this trip.


DIS Veteran
Jul 28, 2008
Congrats on planning! I just love the planning. I think you're idea of planning one meal a day is good. I've been on a few group trips where I was the planner and the 1st trip I planned way too much. Too many meals, too many activities, etc. The best trip we planned which park for the day ( using touring plans for the crowd calendar ) and a sit down meal for that park.

The rest we let people join us at said park when they wanted. So if someone wanted get up early and have breakfast and go to the park then they wouldn't have to wait around for the others. On that same vein, someone wouldn't have to get up early daily to join the others.


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