Milwaukee To Disney: Planning Our Disney World Trip

We recently took a drive from Milwaukee To Disney. My kids are getting older and I am not sure how many opportunities there will be for family time. So I figured why not do a road trip! Quite a few people looked at me like I was crazy when I told them my plans but it sounded like fun to me.

I have wanted to take my family to Disney World since I went there on a blog trip in 2009. Since we have not been on a family vacation in a few years I threw the idea out there to my husband back in January. I was really surprised he was all for it.

Milwaukee To Disney

Where To Go To Plan A Disney World Trip

The first thing I did was go to the Disney website. I registered and selected everything I wanted to do for a trip. I didn’t hit buy right away though and I am glad I didn’t. After talking with a few friends, I learned that there are travel agents whose primary focus is planning Disney trips. There is not extra cost to use these travel agents and they can help you get the best deal. I did a little research, read some reviews and decided to go with Small World Vacations.

It is very easy to get a free Disney World quote from Small World Vacations. I went the route of a guaranteed quote because no matter what I was booking this trip. The questionnaire that you need to fill out is not very long and the information you need to supply includes:

  • Names and ages of guests in your party
  • Dates you plan to stay
  • If it is a special occasion
  • Type of theme park tickets you want
  • Resort you want to stay at
  • If you want a dining plan

I had no idea what the best resort would be for us. Luckily when choosing where I was wanted to stay there was information about which hotels were best depending on the size of your party. The resorts are also sorted according to cost:

  • Value
  • Moderate
  • Deluxe

I ultimately decided to go with Port Orleans: Riverside. I always wanted to go New Orleans so what better way to get a little taste then while at Disney World?

I went with the  Magic Your Way Plus Dining Vacation plan. I did not want to worry about staying on budget while eating out during our vacation so the Disney Dining Plan seemed ideal for us. I will be discussing this further in a later post. My husband had friends who used it and were pretty happy with it.

I added the Disney Memory Maker to our package as well. I did not want to lug my big camera everywhere plus I wanted to be in the pictures instead of behind the camera. I had access to our pictures on my phone within the hour. This made it very easy to share pictures on social media and with my family, #MilwaukeeToDisney . After the trip I was able to download high quality copies to my computer to print later.


Once I reviewed the quote that the Disney agent sent me, I made a $200 down payment on our vacation. This helps them to put your room on hold. Our remaining balance was due 30 days before our trip.  I really liked that my agent kept on top of searching all new discounts and sales that became available to see if they applied to our reservation. She did all the work so I didn’t have to. Amelia did a great job of answering questions and reminding us to set up dining reservations, customize our Magic Bands and reserving our Fast Passes.

Another advantage to booking with Small World Vacations was a one year subscription to Touring Plans. This site is very useful for setting up a game plan on visiting parks. I used it to decide what parks I wanted to visit during our vacations and what rides and shows we wanted to see. I was able to set up an usable itinerary. It helps my stress level to have some sort of plan and an idea of what to expect. It even allows you to add breaks and meals. Touring Plans is a great resource and time saver. I plan on using it on our next trip to Disney.

Stay tuned for my next post where I talk about what I bought before our Disney trip.

If possible sign up for the MouseSavers Newsletter when you are thinking about taking a Disney trip. They send out emails with promotional codes you may be able to use when planning your trip with Small World Vacations. 

So tell me, have you been to Disney World before?

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  • Reply Amelia H.

    So glad you had a wonderful family vacation! It was such a pleasure working with you and I look forward to helping your family plan many trips in the future!

    June 26, 2017 at 6:15 pm
  • Reply LAMusing

    Mom and I went on a road trip many years ago – a great mother daughter adventure., It included Disney World and Epcot – wonderful!

    June 26, 2017 at 10:00 pm
  • Reply gracefulcoffee

    Planning is always a great idea! This post was super helpful.

    June 27, 2017 at 11:59 am
  • Reply Denise Hoyle

    It’s amazing how a little advance preparation can make your Disney trip so much easier! I only just recently learned about the wristbands and that you can get them in advance. Glad you and your family enjoyed the trip!

    June 27, 2017 at 1:22 pm
  • Reply LaVonne Long

    Great planning tips. I hope you have a fabulous time! We love Disney World!

    June 27, 2017 at 4:28 pm
  • Reply Bridget A

    Planning ahead is always helpful! I hope you have a wonderful time! I’ve never been to Disney World, but I have been to Disneyland… would LOVE to go to Disney World, but we live in Idaho!

    June 27, 2017 at 5:01 pm
  • Reply Leah

    I went to Disney back in 1999…still haven’t taken my kids there. Now I want to plan a trip!

    June 27, 2017 at 8:07 pm
  • Reply Michelle S

    You were very organized for the trip to Disney. We have done 3 trips there and being organized helped a ton!

    June 28, 2017 at 7:55 am
  • Reply Jennifer H

    Disney is the best theme park, but I may be biased living near it all my life 🙂 Glad you all had a great time.

    June 28, 2017 at 8:02 am
  • Reply Cheryl Everitt

    I have actually stressed myself out with planning a trip to Disney. Thank you for sharing your plans and awesome trip. I think I can breath easier now.

    July 2, 2017 at 3:43 pm
  • Reply Michelle S

    My husband and I just went last fall to Disney for the Food & Wine Fest. We celebrated our 20 year anniversary there (but no kids). We would like to take the kids when all the updates are done so we can see them all.

    July 3, 2017 at 9:15 am
  • Reply Janet W.

    We’re going to Disney World in a couple of months and I still need to make an itinerary. That will definitely help us once we’re at the parks and we don’t end up backtracking.

    July 5, 2017 at 4:10 am
  • Reply punkin0001

    Disney is all that it has always said it was. My kids would love to go. I know it looks fabulous!

    December 10, 2017 at 1:57 am

    Disney is the best place for a family vacation!

    January 1, 2018 at 7:04 pm
  • Reply Sue Morris

    I love your family photo from the park! I will be spending a week at Disney with my son’s family. The information you have posted will help out. Thanks!

    January 2, 2018 at 3:49 am
  • Reply texasinak

    We live very close to disney, so we don’t have to travel to go, but with all the options they have it really can be overwhelming for visitors. These all look like great tips to give people going to the parks for vacation.

    January 2, 2018 at 10:24 pm
  • Reply John Smith

    What a fun trip! Those magic bands look crazy!

    January 7, 2018 at 8:11 pm
  • Reply momexptheworld

    Pretty cool, it sounds so much easier when you have agent to help book everything! Looks like a fab time! I like the Disney Memory Maker service, it makes it more enjoyable when you’re not trying to be the one taking photos all day. 😀

    January 11, 2018 at 7:41 pm
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