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Planning the Core of your Trip

Hopefully, you’ve read our piece on a Disney World Planning Timeline.  If not, we suggest you start with that article. There we outlined most things that you’ll need to consider for a Walt Disney World vacation.  The next several articles will break that timeline up into portions and provide more detail. Let’s start with the core of your trip: When, Length of Stay, and Resort choice.  

There is some debate about the best order to consider planning a trip, even amongst the Heyday office.  To give you perspective, here is the logic that I’ve followed when writing this piece. We suggest that you start with when you’d like to go.  We’ll consider whether, crowds, etc. From there, how long do you want to stay? When you’re going may play some part in that, for many it has to do with available vacation.  Finally, your resort choice. Again, when and length of time may impact this but let’s stick with an ideal choice to start. These all together give you an initial budget. If all your choices fall within your currently available budget, perfect!  If not, then we can start looking at compromises.  


Let’s break this down into the two major parts; year and season.  There are a few things to consider when it comes to what year you want to go to Disney.  Some people might choose to wait until something big opens, like Star Wars Galaxy’s Edge.  Others might be waiting for the new TRON coaster at the Magic Kingdom or Remy’s Ratatouille Adventure and Guardians of the Galaxy rollercoaster at Epcot before going.  There is an unprecedented number of projects currently taking place as WDW prepares for its 50th Anniversary.  There is a lot to consider!  Or, do you just ignore all of that and go when works best for you?

My personal recommendation, go when it works best for you.  There will always be construction in Disney World with something new on the horizon.  I say, go when you can and make the most of it. Some people choose to wait and plan around construction or refurbishments.  The risk of this approach is that things happen.  Construction and maintenance run into delays all the time.  This is why we don’t advocate planning around those things.    

Assuming you’ve picked a year, now we need to discuss what season you want to go.  Again, multiple things to consider. There are crowds to take into consideration. While, yes, Christmas is an amazing time in the parks.  You can also expect to see them at capacity almost every day from Christmas through the New Year. In fact, almost every New Year’s Eve Day Magic Kingdom gates are closed due to attendance by mid-morning.  Beyond crowds, there are all of the festivals that take place at Epcot not to mention the seasonal parties at the Magic Kingdom. Even if you’re not planning on attending one of the parties, you’ll be impacted by the adjusted schedule for the Magic Kingdom for them from mid-August through the New Year.  

This is all without even mentioning the various discount offers that Disney typically makes throughout the year.  They have already announced Free Dining Plan offers for 2020 or a room-only discount if that would work better for you.  Also, keep in mind, there is no guarantee that these will be offered each year and when they are the quantities are limited.  

One thing to keep in mind is that crowds are usually highest when the fewest discounts are available and prices are most expensive. That’s an unfortunate double-whammy for those visiting at busy times, but Disney’s pricing is demand-based. We can discuss traditional crowds with you and help you take school schedules, crowds, weather, park hours, and special events all into account.  Before truly solidifying your travel dates, we’ll take a look at the planned refurbishments just to help ensure you don’t miss must-do attractions from your list.  

Walt Disney World is great any day of the year, but we absolutely recommend going any time from October to April. To us, the weather and crowds of the summer months are significant negatives. Can you go during that time and have an amazing trip? Absolutely! If you can avoid it though, we suggest that you do.

If you’re thinking of a November or December vacation, there is so much happening during the holidays that it’s simply too much to list here. Every park, every resort, and Disney Springs all get into the spirit of the season. Mickey’s Very Merry Christmas Party is a special ticketed event at the Magic Kingdom that really should be experienced at least once.  From mid-August until the end of October, there is Mickey’s Not So Scary Halloween Party and the Epcot International Food and Wine Festival.  Both are experiences that you don’t want to miss. The downside to these months, particularly August and September, is the weather. The upside is lower crowds.  Which is why we suggest waiting until October. Although the crowds start to pick up you’re typically past hurricane season and the high temperatures are coming down.  

This really does just begin to scratch the surface of everything there is to experience at Walt Disney World.  There are even more festivals in Epcot, runDisney events for those that enjoy Marathons, and just so much more.


beautiful yellow sunset at Disney World

How long you should stay at Walt Disney World depends largely upon the type of trip you want it to be.  If you’re not much of a Disney fan but are taking your kids on a “once in a lifetime” rite of passage trip, we recommend a Walt Disney World vacation of at least 6 or 7 days. This is not to say that you can’t enjoy your time there with fewer days.  A “quick” trip of 3 days or so can really be enjoyable too.  There are just so many options while in Disney World that the length of time will dictate how much you may experience. 

In addition to visiting Disney’s theme parks, you’ll also probably want to build a day into your itinerary for relaxation.  This mostly applies to longer trips.  During a short trip, you’ll most likely want to maximize that time.  Of course, this all depends on how you define maximize your time.  Spending 6 consecutive days in a theme park can be extremely tiring!  As your travel advisor, one of my most important jobs is to help match your expectations of what you’ll experience.  The exact length will still vary a bit depending upon how much vacation time you have and if you plan on visiting any non-Disney theme parks or destinations. 

In the coming weeks, we’ll have a complete article focused just on this topic of How long to go.  


At Disney, the longer you go the less you pay per day.  It seems odd at first, but it is true.  Single-day Walt Disney World tickets are expensive, but multi-day tickets are much cheaper per day. The cost of additional days on a ticket substantially decreases with each day you add after 3 days. In other words, longer trips are not proportionately more expensive than shorter ones.

pricing chart for Disney park tickets

Whatever you do, don’t wait to buy your tickets at the front gates of the parks, because then you can’t book your FP+ attractions in advance. To make your FP+ selections at the 60 or 30-day window, you must have a valid park ticket linked to your My Disney Experience account.  This will make more sense as we work through the rest of the Timeline.

There is one more consideration when it comes to Park Tickets – Park Hopper or Park Hopper Plus?  The Hopper option allows you to visit more than one Park on each valid day.  For example, by adding the Hopper option you may visit the Magic Kingdom during the morning and then go to Epcot for dinner and fireworks.  Hopper Plus gives you even more options each day.  In addition to the ability to enjoy multiple parks, the Plus option also gives you access to Disney’s waterparks, ESPN Wide World of Sports, Oak Golf Course, and a round of miniature golf at either Winter Summerland or Fantasia Gardens.

These addons are not without a cost.  The value of which we can discuss in regard to your desires for the trip.  Hopper tickets are $60 per ticket for 1-day, $70 per ticket for 2 or 3-day tickets, and $80 per ticket for 4 to 10-day tickets.  The Hopper Plus option costs $80 per ticket, $90 per ticket, and $100 per ticket for the same tiers.

We almost always recommend the Hopper option in conjunction with trips for longer than 4 days.  Less than that and you’re often better served to focus on a single park each day.  The longer the stay, the more flexibility of options you’re likely to want. 


tropical vacation paradise at Disney World

When pricing out Walt Disney World hotels, you’re bound to have some sticker shock. Prices have gone up considerably in the last few years, and discounts are not nearly as abundant as they once were. Debating whether to stay off-site to save money or on-site at Walt Disney World for convenience and to be immersed in the magic? There are pros and cons to both options in the off-site vs. on-site Walt Disney World Hotels debate.  We’ll be happy to talk through all of them with you.  We suggest staying on-site when you can.  The access and ease it provides really can’t be compared.

The on-site resorts at Walt Disney World have the three main tiers; Value, Moderate, and Deluxe.  Which are exactly what their names sound like they are. You’ll also see a Deluxe Villa tier, these are some of the Disney Vacation Club (DVC) Timeshare rooms are that are available for rent.

  • Value Resort Hotel
  • Moderate Resort Hotel 
  • Deluxe Resort Hotel 
  • Deluxe Villa (Disney Vacation Club) Resorts 

Beyond the location and transportation, some of the main perks of staying on-site are the FastPass+ booking window and MagicBands. FastPass+ is the all-digital ride reservation system that replaced paper FastPasses several years ago. 

FastPass+ (FP+)

FastPass+ is a complimentary benefit extended to anyone with valid admission. Each Walt Disney World ticket holder receives three advanced FastPass+ selections for a single park (per day). This service allows you to reserve access to attractions of your choosing at a specific time, with a minimal wait. There are a limited number of FastPass+ allocations for each ride each day.  We recommend you make your FastPass+ selections early in order to have a greater variety of options to choose from. Since all attractions and Character Greetings provide standby entrances, you’re also free to simply plan as you go. Keep in mind, the number of slots is limited. Depending on availability, additional FastPass+ selections may be available to guests once their three initial selections have been used each day. Advanced FastPass+ reservations may be made up to 60 days in advance for on-site guests, and 30 days for off-site guests.

If you want any of the High Popularity FastPass+, and some other popular attractions, having the full 60-day window might be the only way to get them. Many of these FastPass+ experiences “sell out” within hours or days of their 60-day window opening. This becomes significant during your trip because a wait time of 2+ hours is not unheard of for these attractions.  Having a FP+ for select attractions could be the difference between an additional 4-6 hours in line per day and getting to experience other attractions as well or not.

High Popularity FastPass+


Likewise, you should make your FastPass+ selections as soon as your 60 or 30-day window opens. Here are some of the, typically, most difficult FastPass+ reservations to make:

  • Peter Pan’s Flight (Magic Kingdom)
  • Seven Dwarfs Mine Train (Magic Kingdom)
  • Space Mountain (Magic Kingdom)
  • Frozen Ever After (Epcot)
  • Soarin’ (Epcot) 
  • Test Track (Epcot)
  • Flight of Passage (Animal Kingdom)
  • Navi River Journey (Animal Kingdom) 
  • Expedition Everest (Animal Kingdom)
  • Toy Story Midway Mania (Hollywood Studios) 
  • Slinky Dog Dash (Hollywood Studios)

Overwhelmed Yet? Let Us Help YOU!

Heyday Travel Company can plan a Walt Disney World vacation that’s perfect for you. We are a free Disney travel planner with expert knowledge of the entire Disney catalog and Universal Parks destinations. No matter where you want to go, our experienced team is excited to help you make it happen. We provide our service at no charge, so you’ll only have to pay for the vacation itself. If you want help planning a Disney trip that’ll make your dreams come true while also fitting your budget, let’s talk!

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