JenSop: The Singing Traveler!

Idealist. Dreamer. Singer. Explorer.

How to Plan a Disney Trip…


So you’re thinking of going to Disney World….


Yay!  First, congrats on your excellent taste in destinations!


But now what?


Where do you start?


What do you do?


Fear not wayward traveler, for I am here to help you!


For those who have never looked into a trip to Walt Disney World, you might not quite understand what planning a trip here means.  Alas, some naive newbies may think they can just “wing it” and go it on their own with no planning.  (This approach usually results in frustration and a sense of being completely overwhelmed.  And eventually the potential for people who end up not liking Disney.)


Part of why I do what I do is because I truly love Disney World.  And I want others to love it too.  It’s just so wonderful, that I want other people to feel that joy – I want to help in spreading more happiness in this world!


If you’ve never been to Disney World, or it’s been many years since you’ve gone, you will be truly surprised at how big it is, how much there is to do, and how far out you should plan.


When should I book and when should I go?

Well, Disney tends to be busiest when schools are not in session.  So if you want to avoid big crowds, go when kids are in school.  Book out as early as you can, but I definitely suggest at least six months out. Why?  I’ll get into that when start to talk about dining and other activities.


How should I book?

This is the way I explain it to friends and clients.  You can either book through Disney, or book through a travel agent.  Your price will be exactly the same.  That’s right, EXACTLY THE SAME. That free dining promo going on in the fall?  The winter package promo going on right now?  I can get you all those same deals as if you booked it yourself.  Booking through me doesn’t cost you a penny more.  Disney either pockets the commission, or has to pay it out to a travel agent.  Your dollar amount never changes.  What does change is the help you’ll get along the way.  But book through a Disney expert!  I REALLY need to emphasize this!  If your agent doesn’t know what the booking window is for making your dining reservations, or which rides you need to get Fastpass for, you won’t be any farther ahead than doing it yourself.  Use an expert and save yourself from TONS of work and stress!


Should I stay onsite?

Time and time again, I will ALWAYS advocate staying ON Disney property.  I am die-hard when it comes to this!  You get free transportation from the moment you arrive at Orlando International airport until the moment you leave.  Disney takes you to and from the airport and everywhere on site for free.  On site guests also get access to the dining plan – which I ALWAYS use.  And you can take advantage of Extra Magic Hours (EMH) – which means every day a different park is either open early or stays open late JUST for resort guests.  You are completely immersed in Disney’s imaginative and realistic theming your entire trip.  It’s truly like leaving the real world behind.  PLUS, with the new Magic Bands rolling out to resort guests and annual pass holders, only those people have access to the Fastpass Plus system, allowing guests to choose Fastpasses at popular attractions before they even leave their homes for their trips.


Which hotel should I choose?

I recently published a post covering this topic.  I have definite favorites, but I find that I usually like to get to know my clients and their preferences before helping them choose the perfect Disney hotel for them.  Here is a link to my post about Disney Hotels.  But the great thing is, is that Disney has hotels for every guest of every budget level!  What are my absolute top faves?   The Polynesian and Animal Kingdom Lodge and Villas.  Beach and Yacht Clubs also get high marks from me.


Should I get the dining plan?

If you stumble upon the Disney forums, you’ll see LOTS of dispute over this very topic.  There were even some discussions on the forums over a popular travel blog that kind of dissed the plan.  (When the writer of said article clearly was not an expert on Disney.)  Here’s my take.  I’ll make it super clear.  I ALWAYS GET THE DINING PLAN.  The “Disney Dining Plan” (DDP) won’t save you TONS of money.  It will save you a few bucks.  But where it comes out ahead is in how much it saves you from the stress of worrying about your dining budget while you’re trying to enjoy your vacation.  I like being able to go to my dinner and order any entree on the menu without looking at the price – because I know it’s included.

The regular DDP consists of 1 table service credit, 1 counter service/quick-service credit, and 2 snacks per NIGHT of stay.  (So a person staying SIX nights gets SIX table service credits, SIX counter service credits, and TWELVE snack credits.)  Each person also gets a refillable resort mug to use at the resorts.  And those dining credits can be used ANY time during your stay.  Use them all in one day!  Skip some days in the middle!  Use one meal for each evening!  Any combination.  Use them anytime you like.  Combine two table service credits for a signature restaurant or a meal at the castle.  Whatever you like!

New for 2018 vacation packages! Guests have several new beverage options available including non-alcoholic specialty beverages and, for Guests 21 and older, beer, wine and cocktails.

Here are some past blog posts on dining:

Disney Restaurant Recommendations

Disney Dining Reservations 


What kind of timelines do I need to be aware of?

Well, first is dining.  If you want a hard-to-get restaurant or a meal with the princesses in the castle at Cinderella’s Royal Table, you want to book as close to 180 days out as possible.  Especially if you go during a busy season.  Same with Bibbidi-Bobbidi Boutique.  If you have a little princess who wants to get her hair and make-up done by a fairy godmother, you need to be ready to book far out in advance.  And now with the new Fastpass Plus system, you want to start to book your Fastpasses out early.  For on-site resort guests, the time frame is 60 days out.  For off-site guests, it’s 30 days out.  (Another advantage to staying on Disney property.)

You can’t go wrong with making choices far in advance and then changing when you get closer to your date.  (Based upon availability, of course.)


What about park tickets?

People are always looking for ways to save on park tickets.  Here’s a blog post on Disney Park Tickets.  You’ll basically find everything you need to know right there.  Prices go up every year and Disney is ever expanding.  Your park ticket is not cheap.  But Disney is not just some regular ol’ amusement park.  You truly get what you pay for!  It’s worth it!


What should I see?  What should I do?  What rides should I go on?

Here is where having an expert at your hands is priceless.  The best rides.  The best restaurants.  The best adult beverages.  I have must-do’s on every trip***, and I love to share that info.  I help all my clients with those important elements, and I also post about my trips here on this blog.  It’s too much info for just one post right here.  But I would love for you to get some great suggestions from my own experiences.  Just go to the “Search This Blog…” space on the right hand side and type in “Disney.”  You’ll get all kinds of great articles from my trips over the years.   Or go to the top of the right hand column and subscribe to my blog, and never miss a posting.  Or Like my Facebook page about all things Disney called Destination Mouse.  Disney also has a GREAT smartphone app called My Disney Experience that links to your online account of “My Disney Experience.”  This is where you register your Magic Bands, pick your Fastpass Plus rides, you can book your dining, and all kinds of other great stuff.  But while you’re in Disney, you can also check on ride wait times.  (And Disney now has free wifi resort-wide!)


Lastly, know that if you are going to Disney, you are going somewhere where everyone can be a kid, there is endless fun and excitement, and you can leave the cares of the world behind you.  Get lost in the joy, smiles, and magic!


*** P.S.

Summary of my “must-do’s:”


Tower of Terror

Rockin’ Roller Coaster

Pirates of the Caribbean

Space Mountain

Haunted Mansion

Big Thunder Mountain Railroad

Expedition Everest

Kilamanjaro Safari


Avatar Flight of Passage


Le Cellier


Columbia Harbour House

Tequila bar in Mexico in Epcot

Tangeriene Cafe

Yachtsman Steakhouse

Lapu Lapu at the Polynesian Resort

Grand Marnier Slushie in France in Epcot

Margaritas in Mexico in Epcot





Author: JenSop

One of my favorite quotes is, "If your dreams don't scare you, they're not big enough." I guess I've been a dreamer all my life - I set my sights high and then I try to reach the sky. Some might call me a naive idealist, but that's just the way I am. I believe in always taking the high road, I believe in true love, and I believe in treating people the way you want to be treated. If you put good out into the world, good will come back to you! Being the dreamer that I am, I pursued singing as my primary life's calling - I've got two degrees in classical voice under my belt, and I sing just about anything under the sun. I also love a good adventure. Over the past few years, I've done quite a bit of world traveling, and have even lived abroad for stretches at a time: mostly in Vienna (Austria) and Croatia. A few years ago, I was lucky enough to be in the right place at the right time, and I became a travel agent who specializes in Disney vacations. (Seriously, I KNOW Disney - I've been going regularly since I was a little girl - and I LOVE it!) And with all my experience traveling and living in Europe, I'm becoming quite the specialist in that travel category as well. (And last year, I started working as a Tour Director in Central Europe!) As to the other juicy details of my life - I'm originally from Pennsylvania, I'm married to an awesome Croatian man named Miloš who is the BEST adventure partner a girl could ask for. (He's also an expert on knowing how to make me smile.) He's truly the love of my life! I've also had all kinds of other jobs along the way, besides singer and travel pro. (Which is pretty standard for those of us who went to school for music.) I've worked part time weekends as a Disney Princess look-alike for children's parties. I've been teaching for almost 20 years, and have lots of experience in retail and customer service. Oh, and I should also probably mention that I'm a huge Lord of the Rings/Star Trek nerd! :-) Let's all go along for an adventure, shall we?

2 thoughts on “How to Plan a Disney Trip…

  1. I love this, Jen! I wish I could pin it so I could find it easily and keep reading and researching.

  2. Pingback: Disney: All you need to know! | JenSop: The Singing Travel Agent!

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