5 Steps for Planning a Disney Vacation: A Cheapskate Princess Guide

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steps for planning a Disney vacation

Updated for 2018!

So the family has been discussing taking your first Disney World vacation, but you don’t really know where to start? That’s totally understandable, because Disney World is a HUGE place, and the different options you have to customize your trip can seem endless. We’re going to help you get that planning in full swing with five big decisions you’ll need to face as you make your way to Orlando, and we’ll do it with finances in mind. 

Read: Ten and 1/2 Tips for 1st Time Walt Disney World Visitors


Step #1 – When Will You Travel?

This is usually one of the hardest decisions to make when planning a vacation. You have to coordinate everyoneʼs schedule and then try to find dates that match up with low prices, weather, and crowds.


For prices, Disney has several seasons that they consider “value,” which is the least expensive season to travel. The problem with Value Season is school will be in session, and there just are not many days that qualify. These are the dates for 2018 are as follows: 

  • January 2 to February 10, with the exception of Martin Luther King weekend
  • August 27-31
  • September 4-6, 10-13, 17-20, 24-27
  • October 1-4, 29-31
  • November 1, 12-15, 26-29

The next least expensive season is Moderate, with days in the fall. To see the calendar for the remainder of 2018, use this link. 

To Save Money, Visit Disney World During Value Season

These are the best times of year to visit the Walt Disney World Resort if you are looking for low prices. The closer you get to most holidays – summer break, spring break, and especially Christmas break – the higher prices will go. If school is in session, you will typically pay less money. 


There are several seasons in Orlando; locals jokingly call them hot, really hot, and “stay inside” seasons. Here are the average temperatures in Orlando if weather will be a factor in your planning.

Read: 10 Things They Forgot to Mention About Walt Disney World Vacations

Climate Data for Disney Vacation in Orlando


These two articles give you the “best” and “worst times of year to visit WDW in terms of crowds and overall craziness at the theme parks. Hint: if school is in session, crowds will be lower than normal. When the kids are out on vacation, this is the scheduling-best and yet “worst” time to travel to Disney. Crowds levels are connected with accommodation prices in many ways – during the busy times at the parks, prices are generally higher.

What Are the 5 Worst Times to Vacation at Walt Disney World?

What Are the Best Times to Visit Walt Disney World?

When one-day ticket purchases went to a seasonal/tiered system, it was assumed that the holidays may be slightly less busy, seeing how some people may not want to pay higher prices during holidays. This in turn could make other seasons, less busy times of year, more busy as people avoid paying higher prices.

“Less busy” these days in terms or Disney World crowds simply means it’s just not super crazy/ three-hour wait times. Disney is a busy place all year ’round; it’s just crazy busy during major holidays and summer. 

Where will you stay at Disney World

Step #2 – Where Will You Stay?

The Walt Disney World Resort has twenty-five hotels, including Value, Moderate, Deluxe, Deluxe Villas, and a campsite. That sure is a lot of options for your family’s vacation. In deciding on a resort, you need to choose a location that fits your budget and will work with your familyʼs vacation plans and needs.

Rooming options range from $100 to $500 per night room as a starting point, and for time’s sake, we haven’t even really discussed the amenities you get with each level room. The more expensive the room, the more amazing perks you’ll receive.

 Value Resorts

  • least expensive accommodations but smallest sized rooms
  • meals: food courts, pizza delivery
  • two to three quiet and large pools
  • a lot of walking and can be really crowded during busy times of year

Moderate Resorts

  • medium priced rooms – medium-sized rooms
  • bus and sometimes boat transportation to theme parks
  • meals: food courts, pizza delivery, table service (except POFQ) lounge bar
  • most offer quiet and large pools with slides and hot tubs
  • expect to walk a fair amount

Deluxe/Deluxe Villas

  • amazing theming, most expensive accommodations, largest sized standard rooms, interior corridors
  • concierge and deluxe suite options available
  • compact locations, so less walking is required in most instances
  • bus, boat and monorail transportation to theme parks (AK is bus service only)
  • meals: food courts, pizza delivery, room service, table service, fine dining, character meals
  • quiet and large pools with slides, hot tubs & spas
  • other amenities: playgrounds, pool bar, boating, video game room, gift shop, kid clubs, babysitting, health clubs, valley parking, salons, some bunk beds

We’re given you the quickie version here, but this article is the prime resource we have for helping you decide which resort will be the best for you money.

Differences in the Disney World Resort Levels: A Cheapskate Guide

While Orlando is filled with hotels and resorts off Disney property, there are many reasons to stay right on-property with the Mouse.

10 Cheapskate Reasons to Vacation on Disney Property


Step #3 – Tickets!

If you chose one of the Deluxe resorts, you may not even need tickets with so many activities to do on property. But if you are headed to Orlando to visit the theme parks, then once you’ve narrowed down when to travel and picked out a place to stay, now you need to choose what sort of tickets you’ll need.

You need to determine how many days you plan to visit the amazing theme parks as well. We always suggest at least one “down day” of no park activity just to enjoy the resorts amenities and swimming pools.


What You Can NOT Wear to Walt Disney World Theme Parks


Disney offers several ticket options, starting with the Admission to One Park ticket, which is often called a base ticket. This is your starting point. Determine the number of days you want to visit the parks. This ticket allows you to enter one major theme park every day, although re-entry to the same park is allowed. You can add other options to this ticket. These are pre-tax prices for 2018.

Park Hopper Option

By adding this option, you can visit of the four major Walt Disney World theme parks for every day you have tickets. You can add the Park Hopper Option after you have started using your tickets if you realize you want to “park hop,” as in visit more than one park per day.

For adults, using a 4-day ticket as an example.

For children, using a 4-day ticket as an example.

Park Hopper Option

What’s new in recent years is the Park Hopper Plus option: this gives you water park and other fun opportunities.

Read: Disney World Water Parks: A Cheapskate Princess Guide


Step #4 – Purchase the Disney Dining Plan or Not?

Disney offers a food option to their packages called the Disney Dining Plan. There are three options:

  • Quick Service Dining Plan
  • Basic Dining Plan
  • Deluxe Dining Plan

Here is the 2018 cost per person per hotel night for each plan. Every plan comes with a refillable resort drink mug.

  • Quick Service (snack, 2 counter service meals)  Adult $44.13, Child $19.04

  • Standard (snack, 1 counter service meal, 1 full service meal) Adult- $63.70, Child $22.85

  • Deluxe (2 snacks, 3 counter or full service meals) Adult $115.08, Child $35.49

If you are looking to save money on food while you vacation, there are lots of alternatives to purchasing a dining plan, including eating in your resort room and bringing snacks/meals into the parks with you. You are allowed to bring snacks, drinks and coolers into all theme parks and resorts. Use this link for other item restrictions.

What Items Can You NOT Bring to Walt Disney World Theme Parks?

However, if you plan to enjoy any of the amazing Signature Dining experiences and Disney Character meals, then the Disney Dining Plan can save money over the cost of paying for your meals out-of-pocket.

Dining Plans allow many visitors to pre-pay for their food, so once they arrive in Orlando, they are not making meal decisions based on cost. As the cost of the meal plans have risen through the years, many seasoned travelers feel the meal plans are not the deal they used to be.  

best Disney Dining Plan

The Top 20 Best Disney Restaurants, So Says the Fans!

Step #5 – Other Plans?

Orlando has so much to offer besides Disney roller coaster rides. Some will require tickets but many will not. We have links to much more detailed information on some of these activities.

Will you visit Disney Springs, for dining, entertainment, and shopping?

23 FREE Activities at Disney Springs! 

Will you do some shopping at any of the other malls?

70% Off Disney Parks Authentic Merchandise? Cheapskate Bargains Galore!

Will you spend any time “resort hopping” = looking around the Disney Resorts?

Almost 130 FREE Walt Disney World Resort Activities!

For our most detailed article on entertaining yourself in Orlando mostly for free, use this link:

3 Days with No Orlando Theme Park Tickets; How We Survived and Thrived Almost for FREE!

mall of Millenia in Orlando

It’s almost as simple as that. Determine the following:

  • when you will travel and for how long
  • where you will stay
  • ticket preferences
  • meal plans or out-of-pocket meals
  • other plans beyond the theme parks?

And this is enough to get you started on your way to a magical Disney vacation, maybe not in a financial sense but certainly in an organizational direction.

For more ideas on Disney travel, we have an entire page of articles. Bookmark it and the just read at your convenience!

Vacation Planning Tips

Thanks for stopping by, and we’ll see you looking at your calendar, calculator in hand.

To see more of our Cheapskating Guides, use this link.

Amanda, Disney’s Cheapskate Princess


Now let our vacation planner help you plan your trip, totally for FREE!

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Use this link for a free no obligation vacation quote from Mike Ellis, our Disney Vacation Planner with Pixie Vacations.

Call Mike at 919-606-6725 or e-mail him at mike@pixievacations.com.