South Florida Captain Takes Visitors to Cuba With First Legal Yacht Charter

You can now cross the Florida Straits on a yacht like this one.EXPAND
You can now cross the Florida Straits on a yacht like this one.
Photo licensed under the Creative Commons Attribution

Plotting your long-awaited travel to Havana now that American access to the island is getting easier? Forget traveling by plane or cruise ship. Now you can legally get to Cuba from South Florida on a yacht — as long as you’re willing to pay at least $100,000.

Last week, West Palm Beach-based yacht charter operator Paul Madden led the first officially sanctioned yacht charter to Cuba. The four-day roundtrip journey took 12 guests and three crew members from Key West to Havana and Matanzas for a high-style educational tour.

“You cross the Gulf Stream where Hemingway fished, and then you start to see the mountains and then the buildings, and then you come into the port in Havana, and you really feel like an adventurer,” Madden tells New Times. “You sure don’t get that in a plane.”

Madden has been chartering yachts for more than 20 years, through the Mediterranean, Alaska, the Pacific, and beyond. After President Obama’s historic December announcement restoring diplomatic ties with Cuba, he filed an application with the U.S. Treasury, under its amended Cuban Assets Control Regulations (CACR), to expand his charter offerings to the island. He expected the application to be rejected. But after seven months of back-and-forth with government agencies, two licenses arrived July 2, giving him the green light — the first in the nation for a yacht company. 

A CACR License allows for the transport of U.S. citizens and residents from the States to Cuba, within Cuba, and back. And a Department of Commerce export license allows Madden to export a vessel from the States to Cuba and back. The final step is permission from the U.S. Coast Guard to enter Cuban waters — which Madden must obtain separately for each trip.

He then launched Cuba Yacht Charter and began preparing for the first voyage. 

“I had people who had expressed interest in traveling to Cuba already, so I made a few calls and quickly had a charter,” Madden says. “There were people from Michigan, Texas, and Florida. They all wanted to see Cuba.”

The group went to Cuba using “people-to-people” visas, which are for education-based trips. The New York-based Academic Arrangements Abroad crafted the itinerary, which included meetings with artists (such as a sculptor named Manuel), an economic and political briefing, a tour of a chapel, and a choral performance. On land, the group drove around in convertible Fords and Chevys. At night, they headed back to the yacht to unwind, eat, and sleep.

“You go back to your yacht and it’s like a bubble; you’re inside the bubble and everything’s perfect,” he says. “You have food, drink, Wi-Fi, telephone. Also, you're with your friends, and you have a big, private dining experience. You decide exactly what you’re going to have. It’s phenomenal.”

Madden says about 60 charter boats work out of Florida and the Bahamas, and another 200 in the Caribbean. Not all want to travel to Cuba yet, but it’s “a reasonable fleet.”

Sound like luxury? That’s because it is. Madden says the trips cost from $100,000 to $750,000 per chartered boat. But in spite of the price tag, he’s receiving calls every day in "increasing numbers." Many people are interested in Christmas and New Year's trips, so he’s scrambling to find boats and begin the extensive paperwork and checks for passengers.

“People want to get to Cuba before it opens up,” he says, “and before they see fast food on every corner.” 


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