It is not difficult at all. Our trip this past May was our first time offsite too. What we did before our trip was write down every address of where we needed to go (airport, Windsor Hills, Publix, each Disney park, Disney resort addresses, etc.) and load them into the GPS in each of our phones. What we found out once we got to the area is that everything regarding Disney World is well marked and signs visible so we didn't need to really use our GPS much. The main way to get to Disney property from Windsor Hills is the World Drive entrance. Coming out of the Windsor Hills entrance gate you make a left onto North Old Lake Wilson Road and drive until you reach a light/intersection, at the light/intersection make a right onto route 192. You are going to keep straight and you will see signs for Disney World and World Drive. You turn right onto the ramp for World Drive which is the road that will lead you to various points on Disney property such as the parks, resorts, etc. Once you are on World Drive you will see signs for the parks and you will want to get in the lane and follow signs for the Magic Kingdom and Magic Kingdom area resorts and be in the correct lane for the resorts. Again everything is well marked from what I remember so driving from Windsor Hills to Disney property isn't going to be as daunting as it may seem now. Hope this helps somewhat.