10 Vacation Questions Answered by a Disney Travel Agent

Questions for a Disney Travel Agent

Nearly long gone are the days you decided to go to Disney World without doing some sort of planning, like made dining reservations months in advance or made a daily vacation game plan. People who hurriedly pack a bag and jump in the car are gambling on not being able to eat at their favorite restaurant, wind up paying more money for accommodations, and so on.

One way to make sure you have the most up to date information on discounts for your next Disney vacation is to contact a Travel Agent specializing in Disney knowledge.  We asked Erin, our Destinations in Florida Travel Agent, what were the most common questions she gets asked when she speaks with clients as they plan a trip to Disney. Their questions, together with her answers, can help you with your planning

103 Fabulous Vacation Planning Articles for Walt Disney World Fun!

Disney Magic

1. Why should I use a travel agent when everything is so easy online?

This is the number one question I get asked the most. Speaking for fellow Destination in Florida agents, I bet it’s their most frequently asked question as well.  Everything is easy online.  But, Disney destinations are not your normal quick weekend getaway anymore.  There is so much to do and see. You can absolutely book your own trip online and never have any issues.  I did that before I ever became a travel agent.

And I exhausted myself trying to read all the information out there, deciding on what tips were actually the best.  How could I maximize my family’s time in the parks and get the most for our money?  When you have a destination like Disney World (which can include a trip to other theme park attractions in Orlando) or Disneyland or a Disney Cruise, there are SO many moving pieces involved, why wouldn’t you want an “expert” to help you?

You are charged nothing extra to use my services and my expertise.  You might find all of the answers you need online, but it could take a while, and then you still are never 100% certain you are getting the most up to date information from certain sources.

That’s what I give you for free, up to date information from a certified travel professional. I am in your corner from the moment you first ask for a quote, until you come back from your trip.  Your trip is as vital and important to me as my own family’s vacation.  That kind of personal service is not something you can get from just online looking. And my services are free of charge to you.

If You Want to Save Time and Money on Disney World Food, Eat Now and Not Then!

what questions should you ask a Disney travel agent, how to plan a Disney vacation

2. Is the Disney Dining Plan worth it?

Absolutely, 100% yes, it is worth it.  I have visited Disney with and without the Dining Plan. I always tell my guests I will never go without it again.  There is no more economical way to eat while on Disney World property.  The dining plan is a huge savings, and once you break down the costs per person and get your first receipt at a table service meal, you will see just how much it is paying for itself.

Another wonderful piece of the dining plan is that you pay for it up front.  So while you are on vacation and enjoying all of the magic, you are not having to spend any thoughts about how much you are spending on this lunch or breakfast tomorrow.  You are truly free to sit back, relax soak in the magic, and enjoy your vacation.


3. How much will it cost a family of __________(fill in the blank) to go to Disney World?

As much as I would like it to be, this is not a cut and dry question to answer.  There are SO many elements to that question I can never just answer it flat-out.  First, I need to find out a few things from my guests.  How many days do you want to stay?  How much time do you want to spend in the theme parks?  How important are your dining options?  There are so many different ways to make your vacation uniquely your own, to make it magical for you and your family.  I cannot just quote a standard number, because every experience is different, in as much as every family is different.

One of the greatest things about being your travel agent is helping fulfill your family’s individual and unique dreams on your vacation.

MagicBand Accessories: Photos and Prices of the Hottest Disney Park Items This Year!

Should you buy the Disney Dining Plan?, tips for a Disney vacation

4. I want to go to Disney World for the price I saw on the Disney TV commercial.  Can you make that happen?

In a word, yes!  I can build a vacation based on whatever budget range you have.  The price depends on when you are traveling, how long you want to stay, and any extras you want beyond the standard TV ad package, because that can alter the price you saw on TV.

I can guarantee that with our agency, Destinations in Florida,  you will always be receiving the lowest possible package price for your vacation.

5. Do you book airfare?

I absolutely will book airfare for my clients.  However, with air travel, air fares and fees being the way they are today, I have found (and my fellow agents have found) that in most cases clients prefer to book their own air travel because of rewards points, air miles, vouchers, etc.  I always want my clients to pay the least amount possible, so I always make sure I tell them to check airfare on their own too.  There is so much fluctuation with the cost of air travel, I would never venture to guarantee lowest prices on air fare. As one more free service I offer, I will gladly help arrange air travel to and from Disney Destinations.

What Are the Best Times to Visit Walt Disney World?

Disney princess castle

6. We only want to go to Disney World once. What is a good age to take my kids? 

In my opinion, every age is a great age to go to Disney.  If you are worried about your children remembering the vacation, then by all means, you can wait until after they are age five, but 99% of the time, every guest I have who says they are only going once changes their mind. They start going every year or every other year.  I truly enjoyed taking my children when they were ages three and one, because I got to experience it through their eyes.  Of course, they don’t remember the trip, but I do and I always will.  I also enjoy it just as much as they get older, and giving them experiences at Disney World that THEY will remember.  I truly believe everyone feels like a child at Disney.  It is that magical. Any age you take your child will be a magical moment for all of you.

7. Does anyone ever have a bad time at Disney?

This is sometimes a strange question that catches me off guard, because my first thought is, “No, of course not.  How could anyone have a bad time?”  But, I see what people mean.  They listen to me explain all of the magic, and they start thinking I have pixie dust flowing all around me all of the time.  And I do! I love everything about Disney World and Disney destinations, so it is hard to imagine people having a bad time on vacation.

However, it IS possible. You can have a bad time at Disney World, but you have to work pretty hard at it.  If you go during peak crowded times and don’t plan your days around the crowds and seasons, yes, you might not have a great time.

But this is another reason that working with a travel agent is so vital.  I provide my guests with an itinerary where I have studied crowd predictions, park hours, and my agency’s tips and tricks.  Everything we provide our guests is to help ensure that their Disney vacation is a once-in-a-lifetime experience filled with so many magical moments, that even if you were trying to have a bad time, it just wouldn’t be possible.

I want to help you leave the parks planning your next vacation rather than regretting the one you just left.

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

 Cinderella Mural

8. What is the best time of year to travel?

When I get asked this question, I always follow it up with, “Do you mean for crowds or weather?”  The number one best time of year to go to Disney World is probably the end of October/first of November.  This is before “Jersey Week,” which is the week after November elections. If you plan it right and can vacation for 10 days, you could actually experience Halloween and Christmas at Disney World.  The weather is usually great and the crowds are minimal.  People always counter that with, “But we would have to take kids out of school.”  I could do a whole article on why I believe taking children out of school to go to Disney World is not only a good idea, but it is something everyone should do. But I digress…

During the end of October/first of November, you would get to participate in Epcot’s Food & Wine Festival, experience the fall holiday decorations and have great crowd levels.

Another great time to plan a vacation with low crowds is after school starts in September or the end of February/first of March.  A good rule of thumb is to stay away from holidays and when major vacations happen for schools.  I think when you spend that much money and make a huge financial investment into a vacation, you want to get the very most out of the experience.  To do that during summer and/or high crowds and hot miserable weather, sometimes is just not the best way to go.

9. How much do you charge for your services?

I charge nothing for my services, zero, zip, nada.  I am a zero out-of-pocket expense to my clients, and that is truly the GREATEST thing I love about my job.  I get to help my clients and give them my expertise and guidance for free.  This is so important to me, because I don’t have to “sell” myself to anyone.  All of my clients get the best of me as their travel agent, no matter what if they spend $50,000 on a family vacation or $1,000.  I provide a certain level of service and treat everyone as VIPs, because they are trusting ME with their family memories.  Some people are very willing and want to pay for my services, because of their work schedules they can only email me or call me late in the evening.  I am free to you as your travel agent, and in this world where it feels like you have to pay for everything, it is so wonderful to be able to work with families and let them know they never have to pay anything extra to use me.

What You Can NOT Wear to Walt Disney World Theme Parks

Can you have a bad Disney vacation?, how not to have a bad time at Disney World

10. Do I need to make Disney reservations so far ahead?

Yes, yes, yes, and yes.  You don’t need to, but I don’t advise doing it any other way.  When people ask me when the best time to book a Disney vacation is, I always say, as soon as you know you want to go.  Even if you are a year out, you only have to pay $200 to book the reservation. Once you book with me, I send you all of my dining suggestions and the list of character dining experiences.  The more time you and I have to talk about which restaurants you want to go to, the better.  Disney lets you book your dining reservations 180 days (6 months) prior to your trip.  When you book with me, I make sure I call Disney at six a.m. on your 180 day mark and do my best to reserve all of your first choices.  Very popular restaurants, like Be Our Guest, will fill up even four or five months before your trip, so there is a very huge likelihood there will be no more availability.  Along those same lines, if you want to vacation during a busy time or a “crowd favorite” time, locking in your room and room rates are another reason to remember booking early is a big plus.

Now, with all of that being said, I have built wonderful vacations for people who have booked their trip a month before they want to go.  They weren’t interested in highly popular dining and activities, and they were happy with whatever dining reservations were available.  So, while I always say, yes, making reservations far in advance is the best thing to do. My caveat to that is, if you are flexible with what you want to do, I can definitely help plan a very magical vacation!

Why Should YOU Not Plan Your Next Orlando Vacation? To Get All the FREE Stuff!

what is teh best age to take kids to Disney World

One other thing to consider are promotions.  Disney insiders, bloggers, posters, etc., talk about the prime times that Disney usually offers promotions.  Everyone always hopes for Free Dining, for example, in the fall.  Or the Stay, Play and Dine for the spring is another popular promotion.  When a promotion comes out, if you decide to book then, you might not have the six months prior to plan everything out.  So, booking early gives us the opportunity to plan out an itinerary.  If we can get all of that set up and have everything in line, then as soon as a promotion comes out and I can apply it to your vacation, you have won twice.  You have had the time to plan everything and get exactly what you want AND a discounted trip.

Booking early is always my recommendation, for all of these advantages.  But, that being said, with me as your travel agent, you don’t have to.  I can help build a great vacation on shorter notice.  No matter what, because of all of the moving pieces to a Disney World vacation, I just want my clients to have the best experience they can have.  Booking far ahead just gives us more flexibility to make all of your magical dreams come true!

What You Can NOT Wear to Walt Disney World Theme Parks


A big thanks to our Destinations in Florida Agent, Erin, for her questions and answers. I’m calling Erin pronto the next time I start planning my next vacation,

Erin Johnson, our Cheapskate Princess Travel Agent

Erin Johnson, our Cheapskate Princess Travel Agent

Erin is a Disney College of Knowledge Graduate and a Universal Studios & Islands of Adventure Specialist.  She has also recently become a Florida Destination Wedding and Honeymoon Specialist.  She can book and plan your vacation to anywhere.

As an avid scrapbooker and parent, Erin makes sure all her clients know memories are her priority.  Erin’s passion is helping everyone have a once-in-a-lifetime magical vacation, which include excellent customer service, attention to detail, celebrating milestones and bringing families together.

Whether it is a honeymoon, a family’s first visit to Walt Disney World, or an extended family coming together from all across the country, Erin specializes in making sure everyone gets the most magic out of their vacation!

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

Earn $20 Rewards for Vacation Referrals!

Use this link for a free no obligation vacation quote from  Erin, our Disney Vacation Planner with Destinations in Florida travel.  She offers promotions like Disney Trading Pin sets, autograph books, and free Mickey Mouse ear hats for kids under age 17.  We know our readers love free…

Give Erin a call at 214-697-7732, or send an e-mail to erin @ destinationsinflorida.com. 

Great Perks for your Walt Disney World Vacation at Destinations in Florida


Thanks for stopping by, and we’ll see you planning your next vacation…



  1. Lisa N. says:

    These are some great tips, but I have to disagree on one point. I’m sure the dining plan works well for many people, but it’s never made sense for me. I know it’s strange, but I honestly don’t drink anything at WDW other than water so the mug and beverages included with each meal would be a waste. In looking at menus, particularly for quick service, a lot of times I might like the entree at one place but the dessert at another. I’d rather have the freedom to eat wherever I want whenever I want.

    Maybe one day I’ll take a trip oriented around food and do the deluxe dining plan with a signature meal every day. But for the average trip I don’t even consider the dining plan.

  2. Jennifer H says:

    Thank you for the tips! Theses are the questions that I have been thinking.

  3. Angie Fitzpatrick says:

    I have planned multiple trips for our family through the Disney website, this is the first year we have used an agent, we will never plan it ourselves agains.

  4. Vanessa W says:

    I love traveling and hate spending it in lines or sweating my tooshie off! Thank you for the tip on when to travel there!

  5. Angella says:


    1. Make sure they have the Authorized Disney Vacation Planner Logo. Look for the Mickey Ear Hat on the logo and the words must say “Authorized Disney Vacation Planner”

    2. Make sure they are a real company – find the owners name, physical mailing address, and owner’s telephone number.

    3.. Never pay a “training or marketing fee” to “join” them.

    4. Call the owner and speak with them so you get a feel for the company and what they do and offer.

    5. Call or email two travel agent that works there. Are they getting paid their commissions?

    6. Call or go to the FL seller of travel website and make sure the company can legally offer travel.

    Destinations In Florida meets all these!

  6. Deb L. says:

    The Dining Plan does not save most people money. Unless you have children under the age of 9 and book multiple character meals the dining plan is not a “huge savings.” And from a business and financial perspective, there is no way Disney would offer the Dining Plan if it didn’t make them money. We have done the price crunching every year for our trip by looking up the menu for each restaurant for every day of our trip and then calculating the total including tax and tip for what we would order. There has not been one year (over the past 5 years) that the Dining Plan would have saved us any money at all. The least amount of difference between the two numbers was $100 and it was the Dining Plan that was $100 more. Please do not continue to unequivocally state that the Dining Plan is a “huge savings” for every family that visits Walt Disney World. That claim is just not true for the majority of guests. Unless you do the work and run the numbers for your family, for your trip, you cannot know if the Dining Plan will save you any money at all.

  7. Excellent post. I was checking constantly this blog and I’m impressed!
    Extremely helpful info particularly the ultimate section 🙂 I maintain such information a lot.
    I used to be seeking this certain information for a very long time.
    Thanks andd good luck.

Speak Your Mind