Sailing to Cuba

Navigating the Murky Waters of Red Tape Despite all the hullabaloo about how relaxed travel regulations regarding travel to Cuba will make the 90-mile voyage from the United States mainland to Havana a reality in the near future, it’s not that simple.

A diligent search of the internet, numerous phone calls with government officials, and even a chat with the commodore of the Havana International YC yielded little in the way of concrete information about when and how one might make this trip by private yacht without: a) being fined; b) losing one’s boat; c) ending up in jail; or d) all of the above.


If you yearn to savor a perfectly-iced Mojito and tightly-rolled Havana Cigar in Havana’s Plaza de Armas before the horde of polyester-clad American tourists turns the Malecon into South Beach, my best advice is to book a people-to-people tour now and wait until the picture regarding sailing to Cuba becomes clearer in the months ahead.

This much is fact: The U.S. government has relaxed its rules regarding what constitutes “legal” travel to Cuba and has eased charter flight requirements and spending limits. U.S. credit card companies will begin to process charges in Cuba in March. U.S. airlines are applying for permission to land regularly-scheduled, non-charter aircraft. Individuals who fit into one of a dozen “approved” travel categories can now travel via chartered airline to Cuba without having to obtain a formal “license.” Under these new rules, a U.S. citizen need only to attest that he/she participated in one of these “approved” endeavors in order to fall under the provisions of the general license category.


These categories include: family visits; official business of the U.S. government, foreign governments, and certain intergovernmental organizations; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic, and other competitions, and exhibitions; support for the Cuban people; humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or information materials; and certain authorized export transactions.

The new regulations remove the per diem rate previously imposed on authorized travelers, and there is no specific dollar limit on authorized expenses. (See resources at the end of this article.) So a sailboat regatta or a fishing tournament is an “athletic competition,” right?

Not so fast. To qualify under even the new regulations, participation in such an endeavor must conform to some specific criteria (see resources). Commodore Jose Eschrich of the Hemingway International YC, Cuba’s affable sailing ambassador, welcomes inquiries and is eager to host visiting yacht clubs from around the world. “We have no specific plans for a regatta this year,” Eschrich says,” but circumstances may change, and when they do, we will make sure our American yachting friends are alerted to our activities.”


Sailing to Cuba with a group may be the less burdensome way to make the trip. Several West Coast Florida yacht clubs have hosted and/or attempted to host races over the years. Check the websites of the Sarasota Yacht Club and St. Petersburg YC  for any news in this regard.

Taking one’s own boat to Cuba is not without some very real pitfalls. The biggest hurdle to overcome is the fact that under present regulations, each boat must obtain a temporary sojourn permit from the U.S. Department of Commerce. This is like an export/import license for your boat. You can make application for this permit at the U.S. Department of Commerce’s website. Expect a delay of up to six months prior to approval … if at all. As of this writing, permits “are reviewed on a case-by-case basis when they are used to deliver humanitarian goods or services or when their use is consistent with the foreign policy interests of the United States.”

Recently, several Cuba veterans have shared their experiences and knowledge with boaters and sailors at a number of forums and in SpinSheet. Annapolitans Duncan Spencer, Dave Dunigan, and Ashley Love completed a six-week trip to Cuba last year. They departed from West Palm Beach and spent significant time cruising the eastern coast of Cuba. Find their exploits in the October and November issues of SpinSheet.

Ashley introduced the trio’s movie “Bartering with Whiskey” to a packed house January 28 at the Boatyard Bar & Grill. “There was tons of interest in our trip,” says Ashley. “We traveled under a journalist’s permit. But that’s all changing now. If you want to go, keep your ear to the ground. Make sure you are appraised of all the current rules.”

Canadian Captain Cheryl Barr, a veteran of more than a dozen Cuba cruises, spoke at length at Passagemaker’s Riviera Beach Trawlerfest last month. She and her father are the authors of pair of the definitive Cuba cruising guides. She cautioned cruisers to “be prepared” with spare parts, fuel filters, and toilet paper! She and her father maintain a website. Check it out for charts, tips and current information.


The author at home

Sailing writer Wally Moran, another Cuba-cruising veteran, has also weighed in about how the new rules will affect cruising sailors. He calls the situation “complex” and “daunting,” yet he believes that at the end of the day, reasoned heads in the government will be convinced to permit cruising sailors and boaters a hassle-free Cuban experience. Wally’s blog, sailfeed page, and his new Facebook group will address issues of interest to the potential Cuban visitor.

If seeing Cuba from the deck of a cruise ship is more to your liking, at least one Canadian-based company offers seven-day luxury cruises to Cuba with weekly departures from Montego Bay. Prices start at $700 per person, double occupancy. With stops at five ports of call, this is a good way to get a feel for Cuba while enjoying the amenities a trip in a cruise ship affords. So close … and yet so far.

The best advice for a potential Cuba trip is to keep checking the sources in this article. At some point in the near future, expect the U.S. government to clarify the rules regarding private vessels going to and returning from Cuban waters. Until then, enjoy a Mojito at your local sailing pub and slurp some great black bean soup at a Latin American restaurant. With the speed at which Washington works, this may be as close as you get to Cuba for a long time!

Story and photos by Craig Ligibel

Resources FAQ on regulations Breaking Cuba travel news License to visit Cuba Upcoming events at Hemingway International YC Capt Cheryl Barr's website