The plan is to hang in the keys, if weather is good to the SW then head to the dry tortugas, around cuba then to Isla Mujures, possibly cancun/cozumel then down to belize.
if weather is better to the east head to the bahamas, then possibly to the turks/ DR/sanjuan and so forth.
Pretty lofty float plan....
Safety of my family is/always will be first, we have much more survival/first aid training than the normal family as most of our family vacations are far off the beaten path where only a highly modified 4wd and a long hike will get you there and back. We will have an emergency life raft/back up hand held gps/epirb/flares/etc
Can you not see how the two quoted sections don't go together? You share that you plan a potentially Quixotic adventure while at the same time claiming safety for your family? I don't get it.
I have shared several things that will strengthen the boat, albeit at expense of comfort, and ironically at the expense of safety if you add too much in the wrong spot. I am not a naval architect, and I know you aren't either. Cause and effect is a crap-shoot when you go re-engineering a boat that is already really good for what it does but limited in other areas. Unfortunately, offshore passage making is not in Mr. Butler's design.
You don't need to be Mr. Howell and you don't need a 40'-plus boat to do your proposed trip/adventure. There are several affordable blue water boats out there that can be had for the cost of just barely more than a really nice C22, some even at 20-feet.
If you aimed your rant at me, it is unfounded. I've only sailed in the Caribbean twice, once in St. Thomas on a 12' resort rental monohull, the other in Jamaica on a Hobie. I was traveling on business, (sometimes my job sucks...

) both times. My sailing experience is largely on Oklahoma waters. They are sometimes very boisterous. My knowledge on maintaining a boat just like yours, (post 86 Catalina 22) is extensive, as unlike your fictional character I do my own work. AND I have done a LOT of work on basically the very boat you intend to go tilting against windmills on. I've been scared Sh£Tless on both my old Catalina 22's and only on fresh water. Unlike a previous poster, I have zero desire to join you even with infinite familiarity with the very boat you intend to use; it is because of this familiarity I find your plan lacking in prudent judgement.
I have shared my cautions because I care. I applaud your desire to cast off and go do exactly what you say you want to. Go for it!!!!!! I just ask you reconsider and figure out how to do it in a different boat. Fix the Catalina up. An 88 is a NICE boat! Use it, at home, and make it shine like a diamond! Sell it to a worthy new owner and apply those funds towards an inexpensive small blue-water boat.
I am comfortable sharing this post as I feel it at least falls on the majority side of sentiments following this thread.
I have told you things to do to improve on the ruggedness of the boat. I have not done so to lull you into a false sense of security in thinking that doing these things will magically give your boat capabilities it wasn't designed for. Even with all the beefing up, the Catalina 22 is still a fresh water and coastal day sailor. Do a bunch of mods? What you will get is a beefed up fresh water and coastal day sailor.
Sorry, sincerely. I know you don't want to hear it, but I am the guy who will tell the Emperor he is wearing no clothes....