I carefully read your latest post, regarding this being in the planning stage and the desire for "bragging rights."
Obviously it would be an adventure. And, I am someone who respects adventure and adventurers.
In fact, when I was in college, I tried, unsuccessfully, to get a friend to canoe with me down the entire Mississippi
River. Unfortunately, my friends thought I was crazy and I did not make the dream come true. So, I understand some of the desire to do something like you propose.
Just be prepared for many people to be critical of the plans, the attempt, and only quiet their criticism when the attempt becomes a "success."
So, here is a little more blunt and honest "criticism" that I hope will ring a reality bell or two. I offer this all in a truly friendly tone of voice with the sincere intent to help.
1. The plan sounds foolish to me,
because it seems to equate "river kayaking" (going downstream) with "crossing an ocean passage
between islands, one that has known strong currents going between the islands and out to a very large sea."
The current is not going from one island to another. It is going between them (perpendicular course).
Can you paddle the 100+ miles between the two islands I listed above without being blown or pushed by the current to the West so far that you miss the target island? I doubt it! Not unless you have planned a route
with a lot of "Easting" to head
to the east so your deflected course will arc
to the target. Otherwise, I suspect you will find your kayak (single or double) is being pushed towards Central America
2. Using a "support boat?"
To me that sounds very "wimpy."
In fact, I have always been amused by the people seeking to set a "record" who go for some kind of distance, all the time knowing that help is just a few feet from them in the support boat.
For example, I acknowledge that the people who swim the English channel
do so by swimming under their own power. That is a long distance (20 miles or more). BUT, the real distance to "safety" is only a few more feet from them, as their support boat is just a few feet away at all times. Some are literally swimming a few feet (5 feet) behind a small boat.
So, the "risk" of that distance is minimized and so the accomplishment seems "bogus" to me.
This is not to say they are not good swimmers and it is obvious they can swim a long distance. And they may have been the first to do some route. That is possible. Recently Dianna Nyad swam from Cuba
to the USA. That was a first. She is mature adult, and so that is admirable too (she is not some young Olympian). She also gets points for trying several times.
But, because the "safety" of the boat a few feet away from them diminishes the real risk, it seems somewhat "false" and "artificial" to me. Almost as if they are swimming in a pool where the side of the pool is just a few feet from them at all times.
Perhaps that is the curmudgeon in me speaking here.
The use of a support boat just sounds like "I am too concerned about my safety" and "I know this is ridiculous but I still want to claim I did it on my own.
" And, "If I wimp out, or need to give up, I need only call my friends on the support boat that is a few feet from me to pick me up."
Another example comes to mind, that of a tight-rope walker. If the person walks without a net between two tall buildings (or over Niagra Falls) that is a real risk and real feat. On the other hand if that same distance is covered with the tight rope
just 3 feet from the ground, it is bogus. The same distance may have been covered, but the risk was minimized.
My Advice on Record
If you really want bragging rights, then do something first, do something dangerous, and do it in such a way that there is a real risk to you (alone) and no risk to others. If you fail, that is part of the risk, but at least you tried. If you risk dying or come close to it, that is part of the "reward" of a success and THAT is your real bragging rights.
If you go wimpy and have a safety
net under you the whole way (e.g. a close support boat) then you might as well use a paddle boat or swim while sitting in an inner tube or use the faddish standup paddle board or do it blindfolded or something silly like that.