The Disney World Do-Over: Tips for Planning a Better Vacation

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the best Disney vacation tips

Updated for 2018!

If you’ve ever planned a Disney World vacation, you know choices and decisions can be daunting. A big fear many people have is trying something new; sometimes it is really, really tough to get out of your WDW comfort zone. High expectations combined with the knowledge of how much money it will cost to get to Orlando can lead many people not to make decisions or make choices they later regret. Good thing for Disney park veteran travelers, it’s easy to look back and decide what you should or shouldn’t have done on a previous trip.

At Cheapskate Princess, we have a wide variety of been-theres and done-thats to call upon their years of experience.

We asked our Cheapskate Princess Facebook Fans to tell us what they would do over again on a memorable vacation. I call it the “Disney Do-Over,” as in, what would you change about a prior vacation if you had known then. Because that wisdom can help some of us now

Read: When Should You Tell the Kids About A Disney Vacation?

how to improve a Disney vacation, fix a bad Disney vacation, have a better time on vacation

How to find the best Disney Word Restaurants

Christie, “Having reservations at Tony’s Town Square. I definitely would have skipped that one. It was one of the worst meals I’ve ever had anywhere.”

Disney World has literally hundreds of restaurants, some with a better reputation than others. Before you make your Advanced Dining Reservations (ADRs), or show up on the spur of the moment hoping to get a table, do some research and check into restaurants you would like to try.

It’s a good idea to read the menu items before you do any planning. I wanted to eat at Epcot’s San Angel Inn for years, but when we looked over the menu, we decided the food options were not what our family would enjoy. Here is an article with a WDW link to menus and instructions on how to access restaurant reviews on trip advisor: Before You Make Your Disney World Dining Reservations, You Should Read These…

When can you save money eating at certain restaurants? Use this article link: If You Want to Save Time and Money on Disney World Food, Eat Now and Not Then!

And when we asked our fans for their favorite table and counter restaurant choices, these are their top 20 picks: The Top 20 Best Disney Restaurants, So Says the Fans!

The Candy Cauldron in Downtown Disney

The Candy Cauldron in Downtown Disney

Staying off property at Disney World

Alexandra, “I had two things on our last trip. #1) Staying off property was a hidden money trap and time-wasting mistake. #2 We did not stay long enough. I fixed that this year; we’re staying at the Art of Animation Resort for 2 weeks!”

There are two definite schools of thought toward staying on vs. staying off property accommodations. Driving around the Disney property can take 20-40 minutes depending on your destination and when you travel, so driving in from off-property can take 30 minutes to an hour, depending on traffic. Many people have to pay to park at the theme parks, which ups your costs even more. And yet staying on property can be rather expensive. Choosing where to stay can be one of your greatest decisions when you plan your vacation.

Our family has stayed off property several times, which saved money and allowed us to bring our two dogs, but the driving gets to be exhausting. You can read about that here: 18 Cheapskate Reasons to Rent a House in Orlando for a Disney Vacation

If you would rather stay on property, there are definite perks in addition to closer proximity to all the fun:Why Extra Magic Hours Are Totally Worth a Cheapskate’s Money!

How to plan a better vacation, Disney vacation planning tips

Don't spend too much on Disney accommodations

Tonia, “My first trip, we stayed at Animal Kingdom Lodge, club level. Like I said it was my first trip. We had NO TIME to enjoy the resort or the amenities it offered!”

Visiting theme parks will take up a lot of time on your average Disney vacation, after all, that’s what most people travel to Orlando for, to enjoy the rides and shows. But if you plan to spend most of your time in the parks, splurging on pricey accommodations may not be the best use of your money. Club Level accommodations might be better saved for several days when you plan to relax at the resorts.

We have an entire list of things to keep you occupied at the resorts without ever needing tickets: Almost 130 FREE Walt Disney World Resort Activities!

Disney World license plate

splurging on Disney World activities

Rebecca,  “MNSSHP. My kids were too young to really appreciate it; the parade was great, but my daughter would have enjoyed doing the Kidcot stations at Epcot that night just as much!”

With tickets running up to $75 for special events like Mickey’s Not So Scary Halloween Party and Mickey’s Very Merry Christmas Party, the cost for these activities can be financially overwhelming. But money aside, lots of vacationers rave about how much fun they had at these parties, as you are purchasing extra time in the parks, with free sugar cookies, hot chocolate, and Halloween candy treats as an added bonus.

If you are paying for the experience, only you can determine what is best for your family. If a character breakfast “splurge” will cost upwards of $200 for a family of five, is it worth the expense for one meal?  If a Christmas or Halloween party will cost two visitors over $125 at a minimum, is it worth it?

It pays to do your research for “events” at Disney. I’ve wanted to do the Tomorrowland Terrace Fireworks Party for years, but the price and only so-so reviews have kept me from following through once I managed to book a reservation. (Can You Afford the Tomorrowland Terrace Fireworks Dessert Party at Disney World?If you are going to splurge on events, make sure your bunch is ready, so you can feel like you got your money’s worth

Christmas at Disney World

Why you should splurge on Disney activities

Chrissy and Jason, “I would have gone to Mikey’s Very Merry Christmas Party when we were there. We were on a tight budget and decided to skip it, but now I wish we would have.”

Briget, “I would book another character breakfast or supper. We did a character breakfast on the last day we were there. It was so much fun!! Our kids really enjoyed spending time with the characters. Next time we do a supper and breakfast!”

You’ve heard of buyer’s remorse? Number five is his naughty cousin, non-buyers remorse. You get home from a Disney vacation, and with loads of time on your hands, you realize all the things you wish you had done on vacation but passed on. This is when you decide if paying for an event, despite the high cost, will be worth it on your next trip.

Our fans have some suggestions for your next splurge: Gotta Have it! 12 Cheapskate Splurges at Walt Disney World

Speaking of a splurge, if you have daughters, this is one “splurge” that rates high among our  Cheapskate Princess Facebook Fans, the Bibbidi Bobbidi Boutique. It’s pricey, but most parents say the experience was well worth the cost. Is the Bibbidi Bobbidi Boutique Worth the Big Buck$? Just Ask a Cheap$kate Princess

If you ever wanted to experience one of Disney’s higher priced events, like Cirque Du Soleil, the Mickey parties, or the Bibbidi Bobbidi Boutique, this may be the year to rectify your non-buyers remorse!


why you should find quiet time at Disney World

Melina, We visited the Magic Kingdom during ‘A Night of Joy’, and it was my 36th birthday. Around 12:30 am, we were walking down the lane in Frontierland, when I just stopped. My husband and I just stood for about 30 seconds; no one was in sight. Not one person, not a Cast Member, not a guest. The lane was empty. It felt like we were the only two people in the park at that time. It is the most magical moment I could ever dream of having. I would try to make that happen each time I go to the MK.”

Disney is a crazy busy place, especially throughout holidays and times when kids are out of school. During these times in the parks, you will be surrounded by lots of crowds, music, parades, noise, and activity. This is certainly not a bad thing, but too much can result in overload for adults and children, most certainly young children. A mid-day break at your resort, visiting other resorts, or simply taking a nap can break up the day into more manageable pieces.

And of course, as Melina points out, things slow way down at closing time, unless you run out of the gates to stand in a transportation line. If you have the mental and physical strength to stay up late, Disney parks are beautiful at night, during the time most people head for transportation home. Stick around to shop or have a snack as the crowds thin out.

Cell phones, tablets and social media can add more craziness to an already frantic day, and here’s why you need less of that: What’s One Thing You Need Less of On Your Disney World Vacation?

Disney World Christmas castle

do not over plan a Disney World vacation

Susan, “On our last morning, instead of just relaxing by the pool or hopping on a bus to visit a park or resort, I wanted the kids to experience the ferry to Magic Kingdom, because we did have time for a few rides and a little shopping. So, having driven to WDW, we drove to MK, missed our turn, backtracked and then attempted parking – ugh! Then, it took so long to get to the Magic Kingdom by ferry.  I wish we would have just taken the bus, stayed a few hours, and then left for home from the resort. Or visited another resort for breakfast or something. I didn’t ‘push’ anything the whole trip and regretted doing so on our last morning. It wasn’t worth the frustration to leave on a disappointing note.”

Over-planning at Disney is probably as common as Mickey Mouse hats. You pay all this money, so naturally you want to squeeze in every minute’s worth of fun. But this frequently just leads to frustration and exhaustion. You can only do so much before the meltdowns begin.

Remember, sometimes less is more.

This is by far our most popular article, with lots of tips on how not to mess up your next vacation, submitted by real people who’ve been there and done it before: 120 Walt Disney World DO NOTs: Tips From Real People on How NOT to Screw Up a Disney Vacation!

Grand Floridian DVC buidling should you drive to Disney World

Susan, “Another thing we regretted doing was driving to WDW from central Missouri. 17 hours was NOT that enjoyable.”

I feel for you guys who have to travel for hours and hours to get to Orlando. Our family has a nine-hour drive one way including lots of stops, but nine is way short of 17 hours, or 30 hours. And for those of you who fly, the cost of that alone makes me cringe.

Weigh very carefully the money saved in a long drive versus the money paid to fly, and then decide what your group can handle. Top Ten Cheapskate Tips Every Disney World Visitor Needs to Know

family can annoy you at Disney World

Rachel,  “We realized that taking more people does not mean you should stay longer. We had a gathering of nine people and stayed ten days. We were tired of each other after five or six days. When we just take immediate family (six), we tend to enjoy the trip for longer.”

Traveling with friends and family can be stressful. While it may seem like a great idea to spend 10 days with family, are you sure you can handle it day after day?

One thing to remember is that you do not have to spend every waking moment together. You can go to different parks and meet up for a meal: Avoid These 10 Mistakes That Can Wreck a Disney World Vacation

Rapunzel bathroom at Disney World

should you go to Disney World the week after Christmas

Ever talked to someone who had a terrible time at Disney World? The common theme I have found is they traveled at the “wrong” time of year, and even more specific, most traveled the week after Christmas. It is crazy crowded from Christmas to New Years, which is no surprise given how many people are off from school and work during this time.

You will have to decide if longer lines are what your family can handle, especially if you are traveling with small children.

And this article is specific for those with their heart set on that uber-popular week after Christmas.

why you don't want to get sick at Disney World

Sara, “If we could do our whole trip over again, we would. My husband ended up with the flu on the very first day at Disney, and on the third day my daughter ended up hospitalized with the flu, steep throat and double ear infections. It was MISERABLE!”

I still remember when I picked up some sort of nasty stomach bug at Disney, riding the monorail, praying I was not going to throw up on a car full of people. I spent 24 hours sleeping off that bug, literally missing the last full day of our vacation. I missed all those last moments –  the last ride, the last snack, the last everything. And then the other four members of my family got it once we got back at home, missing school and work.

What can you do to avoid those nasty bugs lurking on door jobs and metal railings? Wash your  hands and try this: Easy Way to Save Time at Disney World? Buy This for One Dollar

plan a Disney vacation tips

Planning a Disney World vacation

Skyler, “I would have gotten a dole whip when we were in Adventureland. I’ve been craving one since we left 2 weeks ago.”

I am probably the king of this do-over. I see so many things I want to buy to eat or wear that I just can’t afford to purchase them all. Occasionally something will really speak to me, like a t-shirt or a bracelet, and it’s about a 50/50 shot if I will see the item again. There have been times I wished I had bought ______(fill in the blank) right then, because days later, I couldn’t find it, or I didn’t make it back to the resort or park like I wanted.

Disney is a huge place –  there are thousands of food and merchandising items. Sometimes, you have to trust your gut instinct and buy it then, because you may not have the opportunity to purchase it again.

And remember if you decide you just don’t want it or really can’t afford it, if you have your receipt and the item is in just-purchased condition,  you can return purchases to any gift shop, even if you didn’t purchase the item at that location. Now Dole Whips…you better get them right then!

The Most Important Thing You Can Do For Your Disney Vacation? It’s a Four Letter Word!

Haunted Mansion Liberty Bell Steamboat

Don't expect too much at Disney World

Leslie, Mickey’s Not So Scary Halloween Party. The pouring rain really put a damper on it, and we really didn’t do much of what we paid for. We did stay for the later parade though, and my Disney Daughter danced with the Creepa Crew, so it was salvaged, but I was so disappointed. High expectations!”

Your vacation will cost a ton of money, and some people have been waiting years to travel to Orlando. It’s natural for you to expect big things, but not CrAzY big things. You can’t expect perfection to a level that unfortunate mix-ups, cancelled plans, long lines wreck your day or wreck your trip. Things will go wrong, but you simply have to recover.


If you have a Disney Do-over, let us know. It’s always interesting to hear what people would change about their vacations.

Thanks for stopping by, and we’ll see you planning your next vacation, weighing your options for that week after Christmas.

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

Amanda, Disney’s Cheapskate Princess


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