Chartering Cuba

Opportunities for chartering in Cuba are improving for US Sailing hoping to pursue the tropical gem and its surrounding islands.

August 22, 2016
charter cuba
A Dream Yacht Charter cat rests at anchor off Cienfuegos, Cuba. Dream Yacht Charter

As ties between the U.S. and Cuba improve, so too do legal opportunities for U.S. sailors to pursue the tropical gem and its surrounding islands as a bareboat and crewed chartering destination.

Yet limitations persist, and it pays to work with providers who have a thorough understanding of the sailing conditions, the laws (including visa rules) as they apply to U.S. citizens, and perhaps most importantly, the Cuban people themselves. And whether you go with a provider or set out on your own, cut down on unwelcome surprises by finding out what’s expected of visitors to the Caribbean’s largest island.

Among those offering Cuba as a destination to U.S. citizens are broker Paul Madden, Harmony Yacht Vacations and International Expeditions. Madden specializes in crewed yacht itineraries from seven days to a month or longer aboard power, sail, expedition and cruise-type vessels from 43 to more than 200 feet long. These trips, offered on a per-boat basis (charter parties may fill the entire boat, or Madden will match clients to fill it) can include shoreside cultural excursions, gunkholing, and watersports such as diving. Cost per cabin ranges from $8,000 to $25,000 and beyond.


“True charter people, the ones who’ve been everywhere, want to go to Cuba for the art, the music, the culture and the spirit of the people,” Madden says. “That’s what people pick up on. It’s amazing.” Madden also offers paperwork and permit assistance, insurance, and tow-boat services to individual boat owners who intend to cruise on their own.

Brad and Margie Matheson’s Harmony Yacht Vacations, situated at Stock Island Marina Village in Key West, Florida, offers the 90-mile passage to Cuba as a charter, whether aboard the company’s fleet or the individual boats of qualified owners. Upon landfall, Harmony converts the adventure into a two-week land-based itinerary, with the boats functioning as floating hotels. The Mathesons are experienced sailors who have traveled to Cuba for decades for their own group-tour company. They’re also working with the International Seakeepers Society to sponsor flotillas with an environmental focus, and taking steps to open a charter base in the city of Cienfuegos for chartering the islands off Cuba’s southern coast.

International Expeditions, part of the TUI Travel umbrella group, which includes The Moorings, will offer a Moorings 5800 crewed catamaran in Cuba in spring 2017. As for The Moorings itself, the company is exploring plans for a base opening in Cuba in 2018.


Dream Yacht Charter now has a fleet of more than 15 monohulls and multihulls at a base in Cienfuegos. It caters to vacation sailors from countries that already have full relations with Cuba. The company plans to offer bookings directly to U.S. citizens as soon as possible, says director of marketing Brittany Riley. In the meantime, American sailors who acquire the required permits and paperwork independently are welcome to charter with Dream in Cuba.


U.S. Department of State — U.S. Passports and International Travel:
U.S. Department of the Treasury: (type “Cuba sanctions” in search window)
Cuba Yacht Arrangements (Paul Madden):
Harmony Yacht Vacations:
International Expeditions:
Dream Yacht Charter:
“Sailing in Cuba” by John Snyder:
Cuba Boating:


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