Our Story - Who We Are & Why We're Doing This

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Hi! 👋🏼 We’re Robert and Alyssa Simmons. 🙋🏻‍♂️🙋🏼‍♀️ We both love all things Disney and have become those “crazy Disney friends” everyone talks about. 😂 We met in college, and after two years of dating, tied the knot in lovely Indiana. 💍 We then went on a week-long Disney cruise and spent a week at Walt Disney World for our honeymoon. 🛳🏰❤️

We’re both entrepreneurs at heart and have started multiple businesses through the years in various industries. 👢📸🖥 We finally found our niche a couple of years ago, and things have been moving fairly smoothly ever since. We were able to work from anywhere that had Wi-Fi, so we started traveling to see friends and family around the country, go to Disney World often, and enjoy the sites on our road trips, all while keeping our business going. 💻

One day we realized while we were waiting to leave Disney World after another amazing adventure here that we really didn’t have to leave. 😎 We could stay and keep working while being at The Most Magical Place on Earth, but we just laughed and got on the plane to go home. ✈️ As time went on though, we started gradually talking about what it would be like to actually live at Walt Disney World. Crazy, huh? We thought so too. 😉

As we traveled more and more, inevitably our many Disney World trips would become a topic of conversation, and we started learning of stories of family and friends who didn’t have a magical time while they were here at Disney World. 😢 

Of course this made us sad because we love Disney World and the many memories we’ve made together and with our families through the years. ❤️ As more stories unfolded, we started piecing together why we believed some of these vacations weren’t all the families had hoped they would be. 📊

It ultimately boiled down to planning. 📋 A family who planned a year in advance as to when they’d go to Disney World, booked their room nine months out, booked their dining reservations 180 days from check-in, and got the best Fastpass+ experiences at 60 days before check-in had a much better experience than a family that decided two months in advance to go to Disney World and didn’t get to ride the rides they wanted or eat at the restaurants they had hoped for. Both experiences create very different memories, and the latter often has an unwanted ending. 👎 

We wanted to help our family and friends know that they should be planning sooner and how to choose where to stay, what restaurants to eat at, and what rides to ride based on their specific families and interests, but we just didn’t have enough hours in a day to tailor trips for everyone we knew. ⏳

Then Robert, being the numbers guy that he is🤓, started doing calculations on what an estimated cost would be to live at Disney World for a year. 🤔 If we could actually live out of all 32 different resorts, eat at all of the almost 200 restaurants, ride every ride, and participate in all of the extra events, we could document our experiences and put our advice into a website that would allow every family to know when to plan and what they should choose. 🤯 We slowly started making plans and discussing details and logistics of what all would go into something this big and this crazy. 👨🏻‍💻👩🏼‍💻

  • Selling our house ✅ (Our first home 🥺)
  • Selling all of our stuff ✅ (Not as hard to do)
  • A website ✅ (Robert’s pretty good at that😉)
  • Disney apparel ✅ (Of course)
  • No cooking for a year ✅ (I’m in! 💪)
  • No cleaning for a year ✅ (What are we waiting for?!)
  • Living out of limited suitcase space ✅ (Wait…what?! 😦)

That last one was a major struggle for me. I went through my clothes over and over again, narrowing it down more and more. 🧳 No matter how many times I did it, it seemed like I always still had way too much! 👗👚👗 (And I didn’t have Marie Kondo there to help me either!)

We started talking about what we could call our adventure and what all we would need to review and talk about. We made spreadsheets of every restaurant, every resort and room type, every tour, and extra activities. 🗂 We started having garage sales and fixing up our house. 🛠 We backed off traveling so we could focus on this new venture and get everything lined up for this crazy year we had planned for 2️⃣0️⃣1️⃣9️⃣.

And now we’re here! 🎉 We hope you’ll follow along on our adventures this year and share in this amazing journey we’re on! We want to help as many families as we can have an amazing vacation to Walt Disney World, because that’s ultimately what Disney is all about: bringing families together to share in magical memories that will last a lifetime. 💫