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Hit the high seas to this top travel destination

Words: Lizbeth Scordo

With commercial flights from the U.S. finally available, Cuba is currently the hottest travel destination for Americans. But why fly to Cuba when you can sail? Here’s what you need to know to pull it off. 

1. Find a boat

Most sailing trips from the States originate from Florida, with Key West, just 95 miles from Havana, being especially popular. If you don’t have a boat docked there at the moment, chartering one from a reputable company is your best bet. As for boat size: “Any well-built sailboat 25 feet and up will do, with an emphasis on well-built,” says Wally Moran, a cruising expert, writer and author of Cuba Bound who’s made the trip multiple times. Brad Matheson, owner of the Key West-based Harmony Yacht Vacations says the boats he offers for Cuban charters are usually 45 to 55 feet and equipped with three cabins each. Catamarans start at around $9,000 for a week or you can save a few bucks and go with a monohull, which will run you closer to $7,500.  

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2. Know how to sail - Or find someone who does

The trip isn’t usually a difficult one, but it can be, says Moran, as you’ll be dealing with the Gulf Stream. “That current flows against the easterly trade winds and it can make for some very rough water at times,” he explains, adding that you should have a basic coastal cruising standard or better and be well-versed in basic navigation and procedures and how to handle a boat safely. Charter companies will typically send you a questionnaire asking about your experience, sailing credentials and completed courses, but if staffers have any doubts while going over the boat with you, they may ask you to take it for a spin to prove your mettle, says Matheson. (Though lying and then winging it all the way to Cuba sounds like the worst idea ever.) You can always hire a captain to sail the thing for you, which, says Moran, will cost you about $300 a day. 

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A charter boat reaches Havana, Cuba.

© Larry McCart

3. Do the paperwork

In early 2015, the Obama administration made it much easier for Americans to visit Cuba when it expanded the number of approved “general license categories” that citizens can use as reasons for traveling to Cuba. If you make sure your trip falls into one of these 12 (sometimes vague) categories - from education to professional research to support for the Cuban people - then you can visit without approval (though you’ll still need an easy-to-get visa.) Keep in mind that tourism is not a category and you’ll need to do a bit of research before declaring your reason, make sure your itinerary reflects it and have proof you actually did it. Sailors will also need a permit from the Coast Guard, special insurance (which you’ll have to handle yourself only if it’s your own boat) and valid passports for everyone on board.

4. Choose your destination

If you want a good taste of the culture, both guys recommend docking at Marina Hemingway, a 15-minute taxi ride from downtown Havana. Another option is Marina Gaviota, about 100 miles west, in the beach town of Varadero. “But that’s very much of a tourist resort. It’s not close to the communities or what I call the real Cuba,” says Moran. “Whereas if you walk off the grounds of Hemingway, you’ll be in a real Cuban community, away from the tourists.”

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The bright and colorful buildings on the streets of Havana.

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5. Stock your boat

“This is not a consumer society. You can’t just run down to the 7-11,” says Moran. While you can pick up plenty of good stuff at local markets, certain things such as beef, wine and even toilet paper can be hard to come by. You’ll want to bring anything you can’t live without with you. But leave any illegal matters at home (cough cough, pot) because your boat will be inspected upon arrival. Survival necessities would be more ideal. Or any tools you think are essential to survive a trip without WiFi.

6. Get sailing

As with any sailing trip, you’ll be looking at the weather conditions to make sure it’s a good time to go. The trip should take you around 16 hours in good conditions, but it can take up to 24 hours. “I’ve done it when it’s been like glass seas and there are literally no waves at all,” says Matheson. “But three days ago there were 25-knot winds and 4-to-6-foot waves.” He adds that most of his clients either like to leave around either at 2 or 3 a.m., so they’re sailing in daylight for most of the trip or closer to 6 or 7 p.m. so they’re traveling through the night and arriving late morning.

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Completed in 1929, the National Capitol Building is now home to the Cuban Academy of Sciences. 

7. Know what to do when you get there

You’ll radio ahead (English is fine) to the marina to let them know you’re close and then spend about 30 minutes dealing with customs. No need to book a slip ahead, says Moran. There’ll be room. Expect to pay about one dollar per foot per day for a slip. (It used to be 40 cents a foot, but fees skyrocketed thanks to the recent influx of American boats looking to dock.) You’ll want to use the same common sense you do at home, of course, but the Cuban people are renowned for making tourists feel welcome and safe. “I’ve been to 42 countries now and I’d say Cuba is the very safest country I’ve ever been to,” says Matheson, “including the United States.”

8. Heading back

First off, keep in mind that while you can stay in the country for 60 days, your boat is only allowed to stay 14. Fuel will be readily available at your marina, but you’ll probably have enough for the return trip if all you did was sail from Key West to Hemingway. You’ll notify the marina staff and the U.S. Coast Guard 24 hours before you plan to leave and settle your marina fees. Cuban officials will come aboard before departure to clear you to leave and do a final cursory search of your vessel. After you return to the U.S. you’ll need to check in with the closest customs facility (there’s one at the Key West airport). Then, sadly, it’s back to business as usual.

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