For good or ill, the US Government
still has a near-total embargo against Cuba and restricts almost all imports, exports, travel and financial transactions by US Citizens with Cuba.
There are several US agencies that enforce various parts
of the US embargo on Cuba - the Coast Guard (monitors vessels that transit to/from Cuba and watches for illegal immigration and contraband smuggling), Office of Foreign Assets Control (regulates financial transactions with/in Cuba), Bureau of Industry and Security
at the Commerce Department (licenses exports of US consumer goods, including "temporary" exports/sojurns of recreational vessels to Cuba), the Border Patrol (looking for illegal entries of Cuban nationals), Customs
and Border Protection (monitors smuggling to/from Cuba and enforces the OFAC regulations) and Immigration and Customs
Enforcement (investigates human/contraband smuggling and also enforces the BIS and OFAC regulations).
Each of these agencies has the authority to issue monetary penalties for violations. You can go to the OFAC website for example and see monthly summaries of the penalties they assess, and a lot of them are for illegal imports of Cuban products (particularly cigars). BIS issued a number of warning letters a few years back to recreational sailboat and fishing
boat skippers in South Florida
that were involved in regattas and fishing
tournaments in Marina Hemingway, and even arrested and tried to prosecute the organizers (the charges were dismissed, but BIS followed up with monetary fines against the organizers, the details are on the BIS website). The Coast Guard, Border Patrol and CBP can seize vessels involved in smuggling or OFAC violations involving Cuba travel; and they along with ICE have arrest authority for criminal violations of the regulations
BIS takes the position that a US export license
is required for temporary sojurns of vessels to Cuba and as a matter of policy does not grant export licenses for tempoary sojurn of recreational vessels to Cuba.
And the Sarasota
Yacht Club has been trying for several years to obtain an OFAC licnese for a regatta
to Cuba, and recently put on their website that once again they have had to postpone the regatta
since OFAC will not grant them an export license
US policy is slowly changing, but the most recent changes allowing travel and exports are mostly restricted to Cuban nationals in the US with families still in Cuba. There are some exceptions to the regs but they are limited to recognized charitable and journalistic organizations.
All that said, of course US vessels visit Cuba. I personally think there are better things for the US Government
to do, like chasing terrorists and drug criminals, than to arrest and penalize sailboat skippers who want to visit Cuban cruising grounds. But for the moment all indications are that the US Government continues to take a dim view of US citizens and vessels going to Cuba.
We're waiting for US policy to change - my suspicion is that the embargo will remain in place until Fidel Castro is gone, and then it will be lifted. We plan on going the year after that, figuring that for the first year the anchorages
will be filled with US boats that sail down.