How to Have a Magical Proposal at Disney

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It might be the ultimate Disney experience–being proposed to at Disney. I can testify to this, because because I was just proposed to at Disney (hint: I said yes). While no proposal goes perfectly according to plan, ours was completely magical. If you are planning on proposing soon at Disney, here are a few tips from my own engagement that might help you make the most of the magic (and if you want to give your significant other a hint, maybe send this article to them).



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Getting engaged in front of the castle… in the rain. Still a dream come true!!

1. Plan for Weather Mishaps

Florida is infamous for bad weather–no matter when you plan to propose, expect rain. We got engaged during Tropical Storm Debbie, and let me tell you… it was pouring rain all day long. Our portable chargers were soaked and destroyed, and my backpack had a literal puddle of water at the bottom of it. When it was time for my fiancé to propose, the rain lightened just a little bit… then went back to a monsoon as soon as I said yes. We were soaked, as you can easily tell in all the photos. But that’s okay! It’s part of the experience… so go with it! Maybe you take advantage and buy dry shirts that will be memorable for you (there are tons of couple’s shirts in the Disney stores), or you buy a towel to dry off like we did. Whenever you go, bring ponchos… and just make sure the ring stays dry. Rain is always possible in Florida!




2. Plan a Special Meal Afterwards

When I planned for us to eat at Cinderella’s Royal Table, I had no idea I was planning our first post-engagement meal. But let me tell you… it was magical. My fiancé had never eaten in the castle, and his excitement just added to the day’s thrills. When we entered the restaurant, we waited to see Cinderella and show her my ring. Her reaction was priceless, and she responded with such excitement and enthusiasm. Even the cast members accompanying Cinderella were clamoring to celebrate with us!

(Extra tip: Make sure you have PhotoPass so that you can save these special photos!)

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Cinderella was absolutely incredible.. she loved my ring!




3. Don’t Propose in Front of Cinderella’s Castle

Maybe you reread that tip. Yes, I said don’t propose in front of the castle… unless you want a huge, huge crowd of people watching. Maybe that’s your thing (if so, kudos to you!). We wanted a castle view, but a quieter environment. My fiancé and my best friend scoured every angle of the castle to find the perfect spot. Smaller crowds, a stunning view of the castle… what more could you ask for? If you want to use the same spot for your Disney proposal, look for the well on the left side of the castle in front of Sleepy Hollow. There’s a beautiful view, and the only people around will be anyone in line for Sleepy Hollow! Plus, if you time it right like my fiancé (unintentionally) did… you might get some fireworks from the show in front of the castle!

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Did we time the fireworks intentionally? Nope… just an extra sprinkle of pixie dust!!




4. Get Celebration Buttons for Your Engagement

Disney has all sorts of FREE keepsakes for your trip… including your engagement. There are special “Happily Ever After” buttons for engagements, weddings, and anniversaries. They are absolutely adorable buttons, and you can get them personalized with your name, date, or any other information of your choosing. Buttons are a great way to let Cast Members know you are celebrating, and oftentimes Cast Members will say/do something special when they see your celebration button. While you aren’t ever guaranteed anything free (and shouldn’t expect pixie dust)… even the constant and cheery “congrats!” from Cast Members made the buttons worth it for us. Most Cast Members took the time to look at my ring or ask how he proposed, and it made the entire trip special for us.

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The CUTEST Happily Ever After buttons!




5. Plan an “Engagement-Moon” at Disney

You’re already at Disney to propose… you might as well make a trip out of it! My fiancé proposed on Day 1 of a three day trip, and it was so magical to spend the next few days with just a few close friends (who were all in on the surprise engagement). I think the trip was the perfect way to relax after such an exciting, life-altering event, and we got to really cherish all the celebrations. I highly recommend you stay at one of the Deluxe Hotels for the ultimate engagement trip–we were at different hotels for our trip, but we spent a lot of time at the Grand Floridian, where I was staying with my friends… and the romantic vibes of that hotel made everything more magical for our engagement. Plus, staying for a few days allows you to have some undistracted time to chat about wedding planning… we spent a morning with Starbucks on the hub grass in Magic Kingdom and planned some wedding decorations! It was a perfect moment for us.


I hope these tips help prepare you for a magical proposal! Any proposal in Disney will be a moment to remember, so if you are planning on proposing any time soon… consider Disney World! And if you’re waiting for your special someone to propose… forward this blog post to them and give them a little hint.

Here’s to your future magical moments!






author avatar
Erica Herrera
My name is Erica, and I am a Disney-loving adult who just got engaged at Magic Kingdom. I have grown up going to Disney World, and I am currently an Annual Passholder! I love riding Seven Dwarfs Mine Train and eating corn dog nuggets on Main Street.















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