Getting Permission to Sail to Cuba, Chapter 2 of SLOW BOAT TO CUBA

photo-may-08-8-56-35-amThis is chapter 2 of the Slow Boat to Cuba (c) 2016, by Linus Wilson, Oxriver Publishing. It will be available on in late November 2016.


2.Getting Permission to Sail to Cuba


According to my research, only one U.S.-flagged boat received a permit required to sail legally to Cuba in 2014! Regulatory changes in 2015, allowed 90 boats to obtain the necessary permission from the U.S. Coast Guard to sail to Cuba in the first 10 months of that year.[1] My route planning to sail to the Panama Canal via Cuba was made possible based on the changing regulations in 2015, allowing some U.S. sailors to visit Cuba.

There are many tales of U.S. sailors who have violated the embargo and faced no sanction. Nevertheless, if a U.S. sailor violates the Cuba embargo, the penalties can be very stiff:

“Any person …may be subject to:

(1) Imprisonment for not more than 10 years;

(2) A monetary penalty of not more than $10,000;

(3) Seizure and forfeiture of the vessel; and

(4) A civil penalty of not more than $25,000 for each day of violation.”[2]

Starting in December 17, 2014, the President of the United States, Barak Obama, began announcing executive orders which made travel to Cuba easier.[3] The U.S. Treasury’s Office of Foreign Asset Control’s (OFAC) general permit process began on January 16, 2016.[4] The general permit process allowed individual Americans to determine on their own if they fall under one twelve categories. This allowed Americans to travel to Cuba without applying to the U.S. government. Qualifying travelers could visit Cuba with no spending limits while in Cuba and with no prior U.S. government approval under the new regulations.[5] For decades prior, OFAC licenses were almost impossible to get. Even well-qualified journalists complained about how difficult it was to obtain one. Suddenly in early 2015 no application was necessary.

I did apply for an OFAC license in July 2015. The U.S. Treasury wrote back to say no application was necessary as long as I wrote down for my own records why I qualified. I travelled under journalistic license based on my writing in books, magazines, and blogs. The twelve permissible categories of travelers were as follows:

  1. family visits;
  2. official business of the U.S. government, foreign governments, and certain intergovernmental organizations;
  3. journalistic activity;
  4. professional research and professional meetings;
  5. educational activities;
  6. religious activities;
  7. public performances, clinics, workshops, athletic and other competitions, and exhibitions;
  8. support for the Cuban people;
  9. humanitarian projects;
  10. activities of private foundations or research or educational institutes;
  11. exportation, importation, or transmission of information or information materials;
  12. and certain authorized export transactions

Unfortunately, this was not enough. The boat needed an export license. I found from other sailors on Facebook that an export license for the boat could be obtained from the Commerce Department’s Bureau of Industry and Security (BIS) and applied in August 2015. I made some errors in what was a complicated two-page application. It only took about an hour to fill out. BIS also had telephone support that was helpful. The person who checked my application showed me my errors by e-mail and told me to reapply with corrections. In early September 2015, I was granted a 1-year license to take my 31-foot Island Packet sailboat, the Slow Boat, to Cuba.

A few days after I got the 1-year license, on September 18, 2015, export license applications were not necessary for many U.S. boaters. As long as the visit was 14 days or less to Cuba, the boater did not have to apply to BIS. Boaters could obtain general licenses for themselves and their crew (OFAC approval) and for their boat (BIS approval) merely if they wrote down why they were in one of the 12 categories of travelers permitted by the embargo.[6]

I thought I was ready to legally sail for a few weeks. Unfortunately, I soon found out that one more government approval was needed to legally sail to Cuba. Three approvals were needed. The U.S. Treasury’s Office of Foreign Assets Control (OFAC) and U.S. Commerce’s Bureau of Industry and Security (BIS) offer no application licenses. Still one application is mandatory for all boaters. U.S. boaters have to apply for the Coast Guard permit CG-3300 form to legally sail to Cuba.

I sent in my CG-3300 application, which is a simple two-page form, on October 23, 2016. Rosa Garrison, who processes the Cuba permit applications for the USCG, called me a few days after I applied on October 27, 2016. Unlike the folks at OFAC and BIS, Ms. Garrison did not seem to have a good grasp on the regulations and was unable to answer the most basic of questions.

She asserted over the phone that I was going to visit under a temporary (14-day) sojourn from BIS. In fact, I applied and was granted a one-year permit, for which I supplied a license number, on CG-3300. She also asserted that you must return to the U.S.A. under OFAC general licenses. This is only true under temporary sojourns without a BIS application. One-way trips are permitted with BIS applications. Further, OFAC since September 2015 has circulated a FAQ that says that there was no requirement that travelers to Cuba had to return directly to the United States.[7]

After my application languished for a few days, I submitted a Freedom of Information Act Request (FOIA) on November 11, 2016. I requested the submission dates, decision dates, and the decisions (accept or reject) for all CG-3300 applications submitted between January 1, 2014, and November 1, 2015. I did not get a response for the FOIA until late January 2016.

On November 20, I got word that my application was rejected. I immediately disputed the grounds for rejection over e-mail. I was not travelling under the 14-day rule as they asserted. I spoke to the captain who reviewed and rejected my permit, Mark J. Fedor. He granted that they had made an error not reading my BIS export license. Nevertheless, he insisted that I had to specify the names of my crew members on my reapplication. I had left the crew blank. He encouraged me to reapply.

This meant I had to choose a crew member quickly. I had been interviewing dozens of crew members since July. All the trouble with the USCG permit made me risk-averse about selecting an American crew member. I would have to justify why that crew member qualified. I selected my first choice among the crew applicants who were not U.S. citizens. Stevie was a Canadian citizen and backpacker who had lots of offshore in boats in the low 30-foot range. I really liked that he filmed himself living in a cave in the Bahamas for several weeks. Contango had to be a step up from the hot, buggy cave. If he could tough out being a cave man, he was tough enough for life on a small boat. He was my first choice among that pool of applicants. Stevie quickly accepted.

I resubmitted my application with Stevie as crew on November 24, 2015. Captain Fedor reconsidered and approved my Cuba application on November 30, 2015. It took me four months and three applications from three different federal agencies, OFAC, BIS, and USCG, to legally travel to Cuba. My BIS license took about a month as did the USCG permit. I applied to OFAC even though I did not need to which also delayed the process a month. Between the BIS approval and USCG application, I waited over month before filling out the CG-3300.

Based on my research, Half-of-the-time a CG-3300 application has a decision within 13 days. In 10 percent of the cases, a decision is reached only after a month has passed. Some applications are approved the same day. One application took 143 days to process. Since March 2015, the acceptance rate was 95 percent. Prior to that, only 14 percent of applications were accepted. Based on the time until acceptance and the initial rejection, my experience was worse than the typical applicant in the sample. Nevertheless, I suspect that the USCG got very few applications for trips that did not start and end in the U.S.A.

There were 50 times more applications (100 applications) in the first 10 months of 2015 than in all of 2014 (two applications). The changing regulations had a huge impact on the numbers of U.S. boaters seeking permission to sail to Cuba.

[1] I filed a Freedom of Information Request (FOIA) on November 11, 2015, requesting the application dates, decision dates, and decisions for all CG-3300 applications with the U.S. Coast Guard for all applications made between January 1, 2014, and November 1, 2015. That request was replied to on January 26, 2016.

[2] Taken from 33 CFR Part 107.230.

[3] FACT SHEET: Treasury and Commerce Announce Regulatory Amendments to the Cuba Sanctions, U.S. Treasury, accessed online on October 11, 2016, at

[4] See 15 CFR parts 730-774. Accessed online on October 11, 2016 at

[5] Under the new Obama-administration rules, there was no limit on the amount of money authorized travelers can spend in Cuba although exporting goods for sale was generally prohibited.

[6] See

[7] See the U.S. DEPARTMENT OF THE TREASURY, FREQUENTLY ASKED QUESTIONS RELATED TO CUBA which was updated on July 26, 2016, which said, “33. As an authorized traveler, may I travel from a third country to Cuba and from Cuba to a third country? Yes, a person subject to U.S. jurisdiction engaging in authorized travel-related transactions may travel to Cuba from a third country or to a third country from Cuba. Persons subject to U.S. jurisdiction traveling to and from Cuba via a third country may only do so if their travel-related transactions are authorized by a general or specific license issued by OFAC, and are subject to the same restrictions and requirements as persons traveling directly from the United States.” It was accessed online on October 13, 2016, at

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