It might be a good idea to quit the bull at a gate thing, take a calm pill and relax a little. You have gone to some trouble to present information about US - Cuba yacht movements but that information only applies to US citizens, residents and corporations. From what we know so far OP can be classified as "none of the above". I am assuming that he is not a US resident.
There was a link to regulation 746.2 from the Export Administration Regulations
which regulation makes numerous references
to "you". The word "you" is defined this way in section 16 of the Export Administration Act 1979:
" Sec. 16. As used in this Act—
(1) the term ‘‘person’’ includes the singular and the plural
and any individual, partnership
, corporation, or other form of
association, including any government
or agency thereof;
(2) the term ‘‘United States person’’ means any United
States resident or national (other than an individual resident
outside the United States and employed by other than a
United States person), any domestic concern (including any
permanent domestic establishment of any foreign concern) and
any foreign subsidiary or affiliate (including any permanent
foreign establishment) of any domestic concern which is controlled
in fact by such domestic concern . . . "
In addition those regulations
place considerable reliance on the export of US manufactured goods to Cuba but this cat is most unlikely to be such an item.
There might be some issue with re-entry because the entry of any foreign national to the US is a discretionary thing. That is why I suggested that a little subtlety with countries visited could be necessary. Even so the regulations are somewhat in OP's favor. In several parts
of regulation 746 as well as the bulletin linked to above the phrase " consistent with the foreign policy interests of the United States, will be considered on a case-by-case basis " occurs. An immigration official might have some difficulty in showing that a yacht full of Canadians taking a vacation
in Cuba was contrary to those interests, especially in light of what the President has been doing recently.
Finally, snide remarks such as " ask nicely " achieve nothing. In this instance I will not be asking at all.