Here’s a bad idea: apply to the Office of Foreign Assets Control for a license to sail from Martha’s Vineyard to Cuba, have it denied, apply again, never hear back, then decide to go anyway and have the Martha’s Vineyard Times publish a story on your trip. Well, that’s what a guy named Nat Benjamin did and you can read all about it here in the Martha’s Vineyard Times.

Although he timing of the trip is not entirely clear, it appears that Benjamin, who set sail for Cuba in November 2014, arrived in Cienfuegos, Cuba, perhaps luckily for him and his crew, after the new Cuban sanctions rules went into effect on January 15, 2015. According to the Martha’s Vineyard Times article. Mr. Benjamin decided to head for Cuba without the license required at the time of his departure “in hopes that the humanitarian nature of his trip would trump any troubles.”

The question then is whether Mr. Benjamin’s trip fits within the new general license for humanitarian visits set forth in section 515.575 of the Cuban sanctions regulations.

While in Cuba, Mr. Benjamin traveled throughout the country and shared his boatbuilding experience. He was able to contact wooden boatbuilders in the Cuban city of Trinidad.

Mr. Benjamin said Cuba’s wooden boatbuilding industry is not well known outside the country. He partnered with some boatbuilders, hoping to learn about their work, and donated much-needed tools.

Section 515.575 sets forth fairly specifically the sorts of projects that qualify as humanitarian projects, and learning about the work of Cuban boatbuilders, seems to be on the outside edges at best. Here’s what is permitted:

The following projects are authorized by paragraph (a) of this section: medical and health-related projects; construction projects intended to benefit legitimately independent civil society groups; environmental projects; projects involving formal or non-formal educational training, within Cuba or off-island, on the following topics: entrepreneurship and business, civil education, journalism, advocacy and organizing, adult literacy, or vocational skills; community-based grassroots projects; projects suitable to the development of small-scale private enterprise; projects that are related to agricultural and rural development that promote independent activity; microfinancing projects, except for loans, extensions of credit, or other financing prohibited by §515.208; and projects to meet basic human needs.

Maybe this was non-formal educational training on vocational skills, but, even if it does, Mr. Benjamin also needs to be able to prove that he and everyone else devoted a full-time schedule in Cuba to these activities. Having set sail for Cuba before the new sanctions were in effect and with only a vague humanitarian purpose, Mr. Benjamin may not be able to provide this documentation. Perhaps Mr. Benjamin, his wife and his crew are in the clear on this, but this illustrates the potential difficulty in relying on the new general licenses for travel to Cuba without careful preparation and documentation.

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