Recently, my sister’s boyfriend called me to tell me about his plan to propose to her at Walt Disney World. I was incredibly excited to be included in the plan, and to get the opportunity to help iron out important details in the proposal. Below is a list of tips that proved to be beneficial in their engagement, and may aid other Princes in their quest to propose to their Princesses.

The happy couple.

The happy couple.

1. Plan the proposal thoroughly before your trip begins

This may seem pretty self-explanatory and basic. Nonetheless, its importance should not be underestimated.

2. Consider enlisting the help of someone else to successfully execute your plan

For Junior, my sister’s boyfriend, this was my parents and myself. We helped to get Katie, my sister, in the right place at the right time.

The Magical Moment

The Magical Moment

3. Decide where you want to propose

This may require some thought. Do you have a favorite place in the parks? Do you want your engagement to take place in front of Cinderella’s castle? In Junior and Katie’s case, Junior wanted to propose in front of the castle, but he did not want to worry about someone walking in front of them on crowded Main Street USA. He opted to do it in Cinderella’s Rose Garden to the right of the castle.

4. Work out your timing

This can be difficult. Make sure to plan around times when shows or parades are happening that might disrupt your proposal. It also helps to be flexible. Weather can be unpredictable in Orlando and sometimes you have to work around it. In Junior and Katie’s case, we were much later getting Katie to the Magic Kingdom than we originally thought. However, everything worked out because I was in contact with Junior, telling him when we would arrive.

She said "Yes"!

She said “Yes”!

5. Get her to wear nice clothes

We all wear shorts and t-shirts in the parks, but we may not want to get engaged in them. In Katie’s case, I told her that we had reservations at Citricos, and that they had recently tightened up on their dress code.

6. Purchase a Memory Maker

A Memory Maker is a package you buy that is linked to your Magic band or card, which allows you unlimited downloads of the photos taken on your visit. This proved extremely beneficial during their proposal, and as an added bonus we got the chance to take pictures with Disney photographers at any location for the rest of our visit.

Afterwards, the whole family joined in the celebration.

Afterwards, the whole family joined in the celebration.

7. Buy Special Merchandise

While this is not a must-do, it can be nice. Junior bought a glass slipper engraved with their names and the date at Crystal Arts, a glass shop, and also a ring box from The Art of Disney, both located on Main Street USA.

The perfect ending to a perfect day

The perfect ending to a perfect day

8. Talk to Cast Members about what you are planning

Not only will they help, but sometimes they will treat you to something special. Junior talked to a cast member named Gail all day while waiting on Katie to arrive and because their proposal was a “magical moment” she gave them free mouse ears of their choice and a voucher for free prints of the pictures taken during the proposal. While this is not guaranteed, it’s definitely worth a shot.


paul

Paul Little is the founder and president of the DVC Rental Store

close

Receive Specials Straight To Your Inbox!

Sign up below to receive discounted points and confirmed reservation specials straight to your inbox.