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by Disney Magic Diva

Years ago there was a popular parody book called The Best Case Scenario Handbook. Maybe you remember it. It had humorous step-by-step instructions outlining what to do when certain events happened in your life. While it covered things like winning the lottery, what to do when your daughter married Bill Gates’ only heir, or discovering that your distant cousin was royalty, it didn’t address what to do when you win a Disney sweepstakes. I know – because we checked it out when our family won a trip in the Disney Family Time Resolutions Sweepstakes! So here are some tips to help out any other families whose lives are pixie-dusted with a little Disney Magic!

Step 1: Watch your e-mails carefully.
Remember the old adage – you must enter to win! I had been entering my entire family every day during the sweepstakes. One of my sons texted me in the middle of the afternoon one day asking if the contest was still on-going. He said he had received an e-mail from “some company” which advised him he was a “potential winner” in the Family Time Resolutions Sweepstakes, and asked him to confirm his name, address, date of birth and 10-digit phone number. He wondered if it was legitimate or some kind of scam.

Tip: Use caution when entering sweepstakes or providing personal information! Unfortunately, some online contests are scams. Verify the contest is sponsored by the official Disney website or some other organization you trust. Read the rules!

We confirmed the company sending the email was the same company designated as the “judging organization” in the official rules of the contest. I still remember the excitement I felt in that moment! I told him to respond as fast as his fingers could type!

Step 2: Wait to hear back from the judging organization.
This may seem like an eternity. But in reality by the next day my son received an email with an affidavit attached. To be confirmed a winner, he needed to complete paperwork legally swearing to information such as his birthdate, residency, employer, family members’ names and employers, etc. Send back the affidavit and wait again.

Try to remember to breathe. In the meantime, re-read the official rules for the sweepstakes. It will detail the grand prize and all the pertinent information for you. Look for things like if you get to choose which imageresort to go to (ours was between Disneyland Resort and Walt Disney World), how many people get to come (our son got to invite 3 guests to accompany him) length of stay (5 days/4 nights), any restrictions on travel dates, and whether any other goodies are included! (park tickets, gift cards, airport transfers, etc). Remind yourself to breathe again. Try not to hyper-ventilate.

Step 3: Start planning!
Once the judging organization has confirmed you meet all the qualifications of a sweepstakes winner, you can expect contact from the Disney Parks and/or Disney Destinations. My son received a call to confirm he was a winner, and was told he would receive a questionnaire to help start planning the trip. We finally started to breathe again and believe it was real! I think the screaming lasted for several minutes!

The questionnaire arrived in the mail several days later. It asked for information like which resort he wished to visit, his top three choices for dates to travel, preferred hotel to stay at on property, who would be going on the trip, and which airport he’d like to use for departure. This was about the time my son started posting on social media that he’d won a trip and could take 3 guests. It was amazing how many friends he suddenly had! Thankfully, this wise boy of mine remembered who had entered his name in the contest, and chose to bring my husband, his twin brother, and me with him to the Disneyland Resort. Experiencing Disneyland for free was a magical first trip west for our family.

imageStep 4: Be flexible.
Our first three choices for travel dates were all unavailable. Disney only holds so many rooms at each on-property hotel, and if they are unavailable, or in a black-out period, there is nothing you can do but look for new dates. The sweepstakes rules also required that our visit include a Saturday night. So it took some negotiation with a very pleasant cast member before we found dates which Disney had available AND would work with our schedule. While we had hoped to stay at the Grand Californian, it wasn’t available, so we chose to stay in the Disneyland Hotel. We ended up in the original tower, and had a beautiful view of the iconic pool!

Tip: Don’t be afraid to politely ask questions! Since this was our family’s first trip to the area, we wanted to extend our stay and explore other parts of Southern California, especially the Walt Disney Studios in Burbank. Disney was wonderful in accommodating our request!  

Step 5: Relax.
Once you have dates confirmed with Disney, let those cast members work their magic. They’ll send your group all the flight, transfers, and hotel information, and even update you with any changes to your itinerary. Our first flight actually was cancelled by the airline a few weeks before we departed, but Disney took care of everything in rearranging our travel plans.

Step 6: Packing.
You all know the drill here. Each family has different needs when it comes to packing, and you can find great tips from Character Diva here. Make sure your luggage has the right tags on it, you have your vouchers for the Disneyland Express, etc. By now your countdown is probably in single digits!

Step 7: Enjoy.
Take in every moment! We were about to set foot in the park that Walt built, and it was a moment to treasure. Then, of course, there were the free park tickets to enjoy, and deciding how we’d spend the $500 gift card that was part of the sweepstakes prize. I was in favor of buying every Mickey Bar the vendors had, but my son chose to put it towards his next trip to Walt Disney World. So we grabbed a Photo Pass, a new pair of ears and took off to walk in Walt’s footsteps!

Step 8: Post Disney Depression.
Once you’re home, and tax season rolls around, Disney will send you an IRS Form 1099 which will need to be filed with your taxes. To help out my son, and as a way for thanking him for taking us with him, we calculated his tax bill as if he hadn’t won the trip, and then divided the difference between that and his actual tax obligation among the four of us. Not an especially magical moment, but a small price to pay for a visit to The Happiest Place on Earth!

So there you have it. My guide to the “Best Case Scenario: What to Do When You Win a Disney Sweepstakes”. I’m sure you’ll sleep better tonight now that you’re prepared. Just keep entering those official sweepstakes, and hope some Disney Magic comes your way!

***Disclaimer – We at Tips from the Disney Divas and Devos hope you enjoy reading our articles, and encourage you to share any you feel may be of interest to someone else. We do ask, however, if you choose to share the photographs attached to our articles, you give credit to the photographer. Thank you for your cooperation and sharing our love of Disney!

Forever planning our next Disney trip, I've enjoyed magical moments at the Disney Parks with my husband, kids and now grandkids. I hope you will create magical memories with your family too!