OK, I'll offer some comments, based on my own experience cruising Cuba back in 2003, one year before President Bush issued his very tough proclamation restricting sailing to Cuba…
In an effort to be able to claim we spent no money there, we obtained travel visas in advance through the Cuban Interests Section of the Swiss Embassy in Washington… they cost roughly twice what one would pay upon arrival in Cuba, of course… Only problem is, Cuba has a departure fee, so despite whatever measures you take - getting the BS letter from the Club Nautico at Marina Hemingway saying you were "hosted", and whatnot, that departure fee is the one thing you might have difficulty convincing our State Dept. you managed to circumvent…
I did manage to avoid it, I just pulled a runner when I sailed out of Baracoa… One look at the local Patrol Boat, I knew they weren't gonna be chasing me, I doubt they had any fuel for the POS, anyway…
We sailed to Havana direct from Key West, without the supposedly required Security Zone clearance… No problem, it was blowing big out of the NE, we were the only fools out there that day…
Check in in Havana was very straightforward, but extremely tedious, as is dealing with officialdom in Cuba invariably is… One of the best examples of how little they have, most times when officials came aboard to do the reams of paperwork, they had to BORROW a pen or pencil of mine to perform their duties… they were always extremely grateful for the gift of a writing instrument at the end of business… Surprisingly, the only time in all my dealings with officials throughout Cuba anyone so much hinted at a gift "in consideration for their services", was from the doctor who did the medical inspection of the boat in Havana…
Perhaps the biggest misconception about sailing to Cuba, is that a considerable number of Americans were doing it, at least at that time…. My understanding is, there was a bit of a chill in the wake of Bush's proclamation for a year or so, but things quickly returned to normal…
That's not to say many mom & pop cruisers were doing so, however… Most American visitors were of considerable means, lots of 2 million dollar sportfishermen, and so on… Tommy Hilfiger's 170' Benetti TOMMY stayed in Marina Hemingway for weeks, apparently confident Bush was not gonna confiscate someone's $25 million yacht… I've heard that refrain repeatedly from the sportfishing crowd, many of whom simply store their boats in Havana to avoid the obscene marina fees of Key West, and top off with that cheap Chavez diesel…
I had no trouble traveling within Cuba, I rented a car for several days from a resort in Guardalavaca, when I stopped in Puerta Vita… Explored the local countryside, and drove down to Santiago, fascinating travel… Who knows what would have happened if I'd had an accident, but I doubt it would have been as catastrophic had something gone equally wrong halfway across the Gulf Stream on my way there... (grin) Nothing money, or maybe some trinket like my snazzy Seiko chronograph wouldn't have been able to fix, would be my guess...
Another misconception, is that we have no diplomatic relations with Cuba… Well, that may be the official line, but one of the few modern buildings in downtown Havana is a 12 story edifice that is very heavily guarded by police. Don't even THINK about pulling out a camera when you're within sight of that building, no need to ask me how I know this… (grin) But, one thing all the Americans visiting Cuba soon learn - if you lose your passport while in Cuba, that's the place you're gonna head for…
Finally, don't even THINK for a moment that your visit to Cuba might go undetected… A couple of days at Marina Hemingway, you'll soon recognize the local "mole" who strolls the grounds noting the new arrivals, his movements were as predictable as clockwork… And, the Straits of Florida are among the most heavily surveiled waters anywhere on earth… Not only will someone in the US intelligence community know you sailed either to or from Cuba, they probably know what book you were reading in the cockpit enroute… (grin)
Whether they actually CARE, of course, is another matter… I have two clients who took their own boats to Cuba, and received the letter from the State Department eventually… They simply chose to ignore them, and never heard anything further… YMMV, of course, but in this area I suspect our government is largely mostly bark, and little bite - just my own hunch, of course…
Just my own opinion, no one should construe this as any sort of
advice, but I think there is currently little risk for an American to visit Cuba,
as part of an extended, continuing cruise to other parts of the Caribbean basin, or when a return to America is not in the immediate offing Visiting Cuba, then returning directly to the States, could quite possibly be a whole different ballgame, and a chance that - personally - I would not take at this time…
One closing comment of a political nature, if I may… One would really have to be blind to spend much time in Cuba, and fail to appreciate the consequences of our policy/embargo of the beautiful people of that beautiful country… Each country shares the blame, of course, but I really hope we someday soon wind up with an American President with the sort of vision Nixon demonstrated with his overture to China… It would be a wonderful, magnanimous, long-overdue gesture of a great
Statesman, to put aside the petty political considerations of a small bloc of voters at home, and simply declare "You know, I think it's time that the Castros and I sat down and had a little TALK…" Truly pathetic, that a country as great as America, can't seem to bring itself to extend such a modest olive branch to one of our closest neighbors in this hemisphere…
The brief encounter I had with the 3 gentlemen pictured below remains one of my most memorable of my time in Cuba. That is in the lookout tower at Morro Castle, overlooking the entrance to Havana harbor… Those men represent three generations of the same family, the grandfather had been manning that post for over half a century, the radar they were using appeared to be just about as old…
On the right in the background, you can see a series of shelves that house the flags of most of the nations of the world. It is customary at this station, whenever foreign ship enters Havana, they hoist the flag of the visitor's country in salute…
The old man spoke no English, and my high school Spanish is mostly forgotten, but fortunately his son and grandson spoke quite good English… They made it clear, that if the patriarch could have one wish granted in the time that was left to him, it would be to have the honor of hoisting the Stars and Stripes for the first American ship to sail into Havana since the revolution…
I think if I could have a couple of minutes alone with an American President, that might very well be the story I'd share…