Minnewaska, you have a decidedly political take on this issue - something more evident this time around from what I've seen of your comments on this issue in this thread. Cuba, for me, is not a political issue, which is not to say that I don't have an opinion regarding that aspect of cruising Cuba.
My understanding of your laws is that it is legal for an American to go to Cuba provided they do not spend money. Going as the guest of a Canadian or other non-American satisfies that requirement.
The difficulty would lie in proving to your authorities you didn't spend money. I've not experienced that with anyone I know, nor do I expect to, but I would be most interested in hearing from someone who has, and learning what came of it. Thus far, no one has come forward with that story.
As for my experience in getting someone a general license - that's not something I can, or need to, do. That's between the American concerned and your government. I couldn't possibly have any influence on the outcome - so your comment is entirely pointless and is, in fact, provocative.
If you want to pick a fight, find someone else please.
As for illegal activity, I see American boats from 27 footers to megayachts in Hemingway and Veradero every time I go. I have photos, which I won't reproduce so as not to cause difficulties, but as was noted in this thread, someone from the American Interests section out of the Swiss embassy walks the docks at Hemingway regularly and knows full well what's going on. The fact is, with very few exceptions, they simply don't care. If they did, you'd hear about a lot more seizures and prosecutions. Tell me, are you able to name even one boat seized by the US for traveling to Cuba? I thought not, because I just searched and couldn't find one.
Americans are going, illegally, to Cuba all the time. The last figure I heard quoted that I trust was 40,000 annually, going through a third country. Some estimates are over 100,000 per year.
Here, from the State Department, is a short summary of the situation as it concerns mariners:
Cuban territorial waters are extremely dangerous and difficult to navigate, even for experienced mariners. The potential for running aground is very high and the bottom type is unforgiving. Search and rescue capability in Cuba is limited and running aground will often lead to the complete destruction and loss of the vessel. U.S. boaters who enter Cuban waters (legitimately or illegitimately) have encountered problems that required repairs and/or salvage; costs for both are significantly higher than comparable services in the United States or elsewhere in the Caribbean. In addition, the Government of Cuba does not allow the use of the U.S. dollar for transactions and U.S. credit cards are not accepted in Cuba. Cuban authorities typically hold boats as collateral payment. U.S.-registered/flagged vessels belonging to U.S. citizens have been permanently seized by Cuban authorities. Due to the lack of resources, the quality of repairs in Cuba is inconsistent. Repairs take significantly longer in Cuba than they would in the United States due to lack of the most basic materials and to bureaucratic impediments. Boaters are often confined to their boats while repairs are made. Boaters can be detained while Cuban authorities investigate the circumstances of their entry to Cuba, especially if their travel documents are not in order or they are suspected of illegal activities. Mariners and their passengers should not navigate close to Cuban territorial waters without possessing a valid passport, unless seeking a safe port due to emergencies. The ability of the U.S. Interests Section to assist mariners in distress is extremely limited due to current limitations on travel by U.S. personnel outside of Havana. Notifying the U.S. Interests Section, regardless of legitimately or illegitimately entering Cuban territorial seas is the most reliable way to obtain assistance.
The transfer of funds from the United States to Cuba to pay for boat repair and salvage is subject to restrictions codified in U.S. law relating to commercial transactions with the Government of Cuba. A Department of the Treasury license is required for such payments and applicants should be prepared to provide documentary evidence demonstrating the emergency nature of the repairs. U.S. credit or debit cards, personal checks, and travelers’ checks cannot be used in Cuba so boaters should be prepared to pay for all transactions in cash. It is difficult to transfer money to Cuba and travelers have frequently been required to spend several hundred dollars for transportation to Havana to receive transferred funds.
The above information came from http://travel.state.gov/travel/cis_p.../cis_1097.html
. That page also includes the various general license categories with which one can travel legally to Cuba.
Most of what is there is accurate - a bit of it isn't quite how it really works, but that's to be expected. For example, navigating Cuban waters isn't nearly as tough as they make it sound.
If you really want to go, legally, get together with your church and set something up that benefits the Cuban people with your church as the sponsor. Arrange it around your boat if you want to sail there. Or take one of the people to people tours Obama authorized a few months ago.