Cruising Cuba’s North Coast: Practical Experiences and Tips for Visiting Sailors

After making a slow passage along Cuba’s northwestern coast, one correspondent reconsidered plans to continue across the South Pacific. If the short hop a few hundred miles from U.S. shores felt too isolated and demanding, the thought of many more remote islands after a 2,000-mile ocean crossing was unappealing.

“We have been here two months and can hardly believe that we had planned for three … that would have been way too much,” Wendy and Graham wrote aboard S/V Bravo 2, describing the realities of isolation, running aground, difficult provisioning, and constant contact with officials.

Their experience highlights one of the defining features of cruising the Cuban coast: strict in-country controls. The Guarda Frontera regularly boards visiting vessels, and cruisers must clear in and clear out at each port. There have been only a few official marinas along long stretches of coastline, so opportunities to step ashore are limited. At least, as sailors note, the guards generally remove their shoes when boarding.

These port-to-port clearance procedures are often assumed to be a modern product of Cuba’s political system, but their roots are older. Similar systems evolved under Spanish imperial administration to control movement and protect ships carrying treasure back to the mother country. Some nearby countries have modernized their rules: for example, Mexico now offers a one-stop cruising permit system, and the Bahamas has long been comparatively liberal. Other nations, like the Dominican Republic, still operate port-to-port clearance systems that many non–Spanish-speaking cruisers find frustrating, sometimes leading to misunderstandings over fees and procedures.

Author Bruce Van Sant, known for Gentleman’s Guide to Passages South, made multiple small-boat trips along Cuba’s north coast to study winds and develop cruising strategies. He evaluated 20 anchorages based on protection, marina access, provisioning, and whether a Guarda Frontera post was present. Van Sant advises that the absence of a Guarda post can be a positive factor when deciding where to anchor.

When I asked Van Sant for practical advice about interacting with Latin American officials, he drew on decades of experience. He recommends some Spanish ability but warns that full fluency can sometimes complicate interactions — it may create expectations or dynamics that work against you. His core suggestion: answer official questions plainly and directly.

“Answer official questions from Latinos as you would converse with your spouse — carefully but directly,” he says. “You answer trick questions not trickily but dead on. And you accept the consequences, which often [surpass] those that would have come had you answered deception with deception. It works.”

Don Barr, who spent two decades as skipper of the Canadian tall ship Bluenose II and later built a 62-foot Herreshoff schooner, Road to the Isles, has completed multiple cruises to Cuba. He has also coordinated foreign boats getting work done in Cuban shipyards. Barr reports generally positive experiences with Cuban officials, though he stresses the importance of understanding the system.

“Yes, I have seen a few people having problems in Cuba almost every year,” Barr says. “I think the main reason is they just do not understand the system. It is a strong totalitarian government, and we North Americans are just not used to those kinds of restrictions. If the answer is ‘no,’ we want to know the reason why. In dealing with the local officials, it is important to understand that they are just doing a job and also do not know themselves the reasons why. They are all very friendly, and when you understand the procedure you must go through entering or leaving etc., the time it takes, and just roll with it — we have never had a problem.”

Geert van der Kolk, a Dutch novelist and sailor, completed a semicircumnavigation of Cuba in 2007 aboard his 30-foot Dufour Arpège, Sea Scout. His voyage, like many Cuba cruises, was intimate and demanding: three people aboard a Spartan boat for extended stretches. He later summarized his experience in a short list of practical suggestions titled “Ten Tips for Cruising the Cuban Coast.”

Van der Kolk’s final tip is worth repeating as a reminder of the human side of cruising: “Love the people.” He recounts a simple interaction in Havana that illustrates how warmth and cultural references can ease an official encounter. When a uniformed official asked about his profession, van der Kolk said he was a writer. After a brief exchange mentioning Cuban literary names, the official’s assistant smiled — a small human connection amid formalities.

That anecdote underscores a broader point for anyone planning a cruise along the Cuban coast: prepare carefully, be patient with official procedures, keep interactions honest and straightforward, and remember that courteous personal contact often smooths practical challenges. For cruisers, success depends as much on seamanship and provisioning as on cultural awareness and respect for local rules.

Related story titles:

“The two faces of Cuba”

“An advocate in Havana”

This article originally appeared in the July 2009 issue.