We need a new adventure.. Should we do the Great Loop?

This winter I found myself pretty burned out with my job.  Maybe its a side effect of not getting out enough due to COVID?  Anyway I started day dreaming about how we might realistically do the World ARC as a family.  If you're not familiar with it the World ARC is an around the world sail boat rally done over about 18 months leaving from St Lucia.  A few years ago long before COVID we were at the Annapolis Boat Show and were invited to attend a seminar on the World ARC where we had the chance to meet a few couples that had completed the adventure. It sounds like an amazing adventure and Amy really liked that the company provided structure, guidance, and a degree of safety due to the large number of boats traveling together. When we left we both felt it was defiantly something we were interested in sometime down the road...

Well after watching a LOT of YouTube couples and families make sailing around the world look easy and fun I started really thinking about how to get my family out there before Annabelle got too old and want to leave for college in two years. After talking about it a lot as a family it became clear Max was with me and all for the adventure but Annabelle wanted nothing to do with it. Amy was somewhere in the middle with this nasty habit of looking at reality.  She kept pointing out little things like how the heck are we going to home school two teenagers that are not used to that kind of environment while traveling the world without a consistent internet connection and balancing that with good weather windows and a major lack of experience.  After more discussion we started talking about doing other things.. An RV trip across the county came up and was pretty quickly ruled out.  The possibility of taking the boat on the Great Loop came up.  Instead of two years traveling the world this trip would keep us stateside with a possible side trip to the Bahamas (if they open the boarders) and might only take a year.  Giving us some quality time together as a family and some much needed time away from work for me.

We had talked about doing the Great Loop more than 20 years ago before kids.  One weekend when I was stuck in Portland Maine for work I found a book written by a couple that had done this seemly great sounding stateside adventure.  Reading that book made it sound like it was  low risk and could be done pretty easily.  The hardest part was having both the money to afford the trip and the time required at the same time.  Needless to say I had gotten really excited about the possibilities that weekend after a few months even had Amy on board for the adventure.  Shortly after that trip we started looking at boats and eventually saw our first Allmond on Lake Norman when we lived in Charlotte.  Fun fact we almost bought that boat but could not find a dock to keep it at back then.  It only took about 10 more years before we found another one just like it that we ended up purchasing.

So now we are seriously considering taking a year as a family to travel some of our countries best waterways and possibly the Bahamas.  We spent much of February & March talking about how we might make this trip happen.  Do I try to work along the way keeping my IT job?  How do we educate the kids?  Is our current boat the right one for the purpose?  What do we do with our house, cars, and land life commitments.  I don't know the answers to any of these questions but would like to document our decision process and eventually our adventure as we go.