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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. 💫

How are you paying for your year at WDW?

We sold our home which gave us the funds to start booking many of the rooms we’re staying in and the points we’re renting for our DVC stays. We’re also still running our business during our stay, so on certain days of the week, we work on our marketing agency.

The entire year is not paid for even with those things, so we’re working on other ways to bring in revenue, but ultimately, we took the leap of faith because we really believe we can help a lot of people.

What shoes do you wear for all that walking?

95% of our shoes are Crocs. Now before you go thinking we only own boat shoes, Crocs makes a wide variety of stylish shoes that are just as comfortable as the boat ones. We have sandals, ankle boots, wedges, and canvas loafers that are all Crocs brand and look nice while also being comfortable. So we wear those most of the time, and we have running shoes from Fleet Feet for working out, training, and marathons.

How do you stay healthy/fit eating all that Disney food?

We walk a lot which is a huge part of burning off the calories we eat. We also don’t eat full meals. We take pictures of a meal, and generally eat about half of it. Then we save it and eat the leftovers the next day. When we want a snack or any food item, we have to walk to go get it and walk back, so we basically burn off whatever we’re about to eat anyway. We also do try to order greens when possible at sit-down meals and know where some of the healthier snack options are in the parks.

We also take Vitamin C, Young Living Ningxia Red, and use lots of Young Living hand sanitizer and oils. With being around so many people all the time, we work to stay as healthy as possible, but we know there will probably a couple times we may get sick when flu season and other things come around, but so far we’ve made it half the year without any major issues.

How do you keep all the bookings organized?

It’s not easy, that’s for sure. Between changing rooms every 2-3 nights, dining reservations, tours, Fastpasses, festivals, and extra activities, it can be a bit overwhelming. But we use a date-based spreadsheet called AirTable to keep everything laid out nicely and filed in different categories. Then as we stay in different room types or eat at different restaurants, we can mark it off and know how many places we still need to stay in, eat at, schedule, etc.

How long did it take to book everything?

We’re not sure yet. We’ve already spent dozens of hours booking, and we’re still not finished. It’s a lot of work juggling when to stay at what resort based on availability, specials, better deals, and what we still need. So we’ll see when we finally get it all taken care of. As of now, we have 10 of the 12 months booked which is really encouraging.

What are you doing when the year is over?

We don’t know yet. We’re both really big planners, but we decided to see how this year goes. We do plan to visit Aulani next year and enjoy Disney’s Hawaiian cruise. We also have a trip to Disneyland booked, so no matter what we do, of course it will still involve Disney.

Do you work for Disney?

No we do not. We came up with the idea ourselves and are paying for everything from our own pockets. If that ever changes, we will let our readers and followers know in the interest of full disclosure. But as of now, we are not in any way sponsored by or affiliated with Disney.

What is your favorite resort?

Every Walt Disney World resort is unique in its own way, but Robert and I both have our favorites. Robert's favorite resort is Wilderness Lodge because it is close to Magic Kingdom, has a relaxing feel, great decor, amazing cast members, and incredible food options everywhere. He also loves Copper Creek which is located in Wilderness Lodge.

Alyssa's favorite resorts are Coronado Springs and Old Key West. Coronado Springs is a moderate resort that is similar to a deluxe. It has a workout room, spa, amazing food court, great landscape, a wonderful layout (the adult areas are near the main lobby while the pool and kids areas are on the other side of the lake), and amazing service. It's more of an adult resort as it is known for its conferences, so there are more adults here normally. Old Key West has the biggest rooms of any DVC resort and has recently been remodeled. The restaurants have great food, there are lots of fun activities there, and the vibe is much more relaxing than a lot of the resorts.

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