Perhaps it's just me, but I hardly see the point of going to Havana if you're not gonna leave the confines of Marina Hemingway... You're not suggesting you'd actually entrust your family's safety to Castro's police whilst wandering around the streets of Havana, are you?
Yes, yes I would trust them, and would spend most of my time out of the marina. They zealously guard tourists, and will provide escort if requested to common destinations for extremely reasonable rates ($10 RT to anywhere in Havana for example). You will find incidents to be extremely rare, as the punishments to criminals are extremely harsh when foreigners are involved.
Unless things have changed drastically since I cruised Cuba, I think you're in for quite a surprise if you think their policy is "made simple" by virtue of the fact that there are relatively few Ports of Entry in Cuba...
You don't appear to understand that you will be required to check in and out with the Guarda EACH AND EVERY TIME you move your boat in Cuban waters... I have to assume your weapons would be taken from you for "safekeeping" every time you checked in with the Guarda...
Exactly correct, I do understand, and why would I expect it to be different? I'm bringing a weapon into their national territory. I'm grateful that their policies allow me to do so, and will abide by them strictly.
You are under their watchful eye continuously, they will likely dictate where you can and cannot anchor, for example, and any sort of dinghy exploration is generally prohibited... There are exceptions, of course, when you get into remote regions such as the Jardines de la Reina along the south coast, but for the most part each and every time you move your boat, it will be dictated by and subject to the jurisdiction of the Guarda...
More or less correct. By dingy exploration I'm assuming that you mean landing by dingy. Of course it's prohibited, as you aren't at an official point of entry. Trying to do so just because you are somewhere remote and might not get seen is just plain stupid.
Until you've experienced it, there's no describing the virtual paranoia of these officials... Your boat will be subject to routine "inspections" that will easily take an hour or more, each and every time you clear in and out of your next destination... They are obsessive about things like accounting for portable GPS units and outboard motors, I can't even begin to imagine how they would react to dealing with someone who had entered the country with weapons aboard... I can only guess such might complicate your experience to such a degree, you would wind up deeply regretting having decided to visit in the first place...
It seems you are the one with paranoia, not them. They are doing their jobs. They make sure you aren't bringing anything illegal in, and they make sure that the equipment you arrive with is accounted for in case there are any issues later on.
Plenty of people arrive each year with weapons on board. Do some searching on other forums, or just Google. As far as regretting the visit; Your mind seems to be made up, so why would I try to convince you that it would be worth my time, when it obviously isn't worth yours?
Forgive my ignorance of international weapons regulations, but how many countries out there would permit an American visitor to wander around within their borders while "packing heat" for personal protection?
Couldn't say, but I know Grand Bahama and Bimini require a check in of your gun and strict accounting of your ammunition quantities, but then allow you to retain your weapons and ammo. The only reason I know this is because my sail to there is much sooner, so I have already finished doing my homework. I would imagine if I'm 2 for 2 on my first trip then they aren't the only ones in the Caribbean who allow it.
You obviously don't trust American law enforcement for your personal protection while in the States... Just curious, but are there actually ANY countries out there that you would depend upon their law enforcement for your personal protection while in their country?
I do trust American law enforcement officers, I think most of them are hardworking people trying to do the right thing. All of their good intentions, however, do me no good if I wake up to find someone in my house. The police don't do me any good a phone call and 10 minutes away.
Whilst wandering the streets and markets openly, I would trust many countries to keep me safe, but not all, i.e. Columbia, Haiti, Jamaica, some areas of Mexico, etc.
Being prepared and never having to utilize that which you have prepared for is not a failure, it is a success. Not preparing is unwise, and some would say foolish. However, it is your life to risk. I don't have to agree with your choice to sail unarmed and I might try to convince you otherwise, but in the end when you sail off - it is your life and the lives of your crew
in your hands.