December 2020 – Planning

The year 2020 was challenging and as fall approached we hoped to find a way to travel over the holidays. Originally we had looked at going to Dubai for a couple weeks, but with the COVID restrictions that was not even a remote option by the fall. We would restrict ourselves to a domestic destination, preferably a nonstop flight and something we could easily cancel.

We definitely wanted to go someplace warm which got us remembering our last-minute trip to Fort Myers in the spring. We had so much fun at the Hyatt Regency Coconut Point Resort and Spa that we knew the kids would love to go back. That would be good for a few days but we wouldn’t want to stay there the whole vacation so we started brainstorming some additional locations.

Since my wife would have to work most of the days, I’d be the one doing things with the kids. She brought up the idea of going to Disney World which, surprisingly, made a lot of sense. Orlando is only a few hours drive from Fort Myers and since she is not a Disney fan, she wouldn’t be missing out when she was working.

I had taken each of the boys separately to Disney World the year they turned 8. Both trips were fantastic and it was a nice dynamic having only one of the boys at a time. I’d have both of them this time and I hoped that since they had been before and were a little older I could more easily manage both of them. If I could figure out how to make this trip work I’d have to hope we could make them both want to do the same rides at the same time.

General Outline

The general plan would be to spend roughly four days in Fort Myers and nine days in Orlando, assuming flight prices and availability. We’d rent a car and use points for as many of the stays as possible. I would need to take special care to only book things that were refundable.

With a basic outline, it was time to look at flights and get something booked!