With America’s historic relaxation of Cuban border restrictions, comes an opportunity for superyacht owners and charterers to explore its tropical cruising grounds.

However, it’s political landscape remains authoritarian, and its communist history has instilled widespread poverty among its masses, two factors which warrant caution for the trailblazers who intend to traverse this new superyacht frontier.

SuperyachtNews.com spoke exclusively to Ross Thompson, MD of Miami-based private security and intelligence services provider, Classified Worldwide Consulting.

“With the US embassy opening up in about two weeks in Cuba, it’s a signal to Americans that they can start visiting… but there’s a lot of things that still need to be considered”, Thompson explained. “We have a lot of big boats that will be looking to go down there for the great fishing, the beautiful reefs and everything else… South Florida, Cuba and the Caribbean is a very heavily patrolled area – the military, US Coast Guard, ICE and the DEA - so there’s a lot of movement and there are licences you’ll need if you want to operate your yacht there.”


Ross Thompson.

Thompson said that, while UHNW visitors would be seen as an incredibly valuable addition to the country’s tourist economy, yacht owners should be mindful of the levels of state intervention still taking place in Cuba. “Guests should know that nothing is secure in Cuba.

“All of your passwords need to be changed when you depart Cuba [because] the Cuban intelligence service will be picking up those passwords and they will be listening in your cellphone calls or landline calls that your crew might make…and that can be one of the highest risks for high-net-worth people.”

One way to circumvent prying state eyes is to anchor in international waters and tender into port but even this should be supplemented by the use of a local agent. “To have someone there who’s your English speaking local contact is extremely important”, Thompson explained. “There will be certain challenges on arrival; they’re very wary about video equipment, microphones, detailed charts of the coast – the ‘tools of espionage’ – they could be conceived as hostile.”

To the south of the island there is Guantanamo Bay, which is highly restricted. Anyone planning to transit the vicinity should make it abundantly clear to US authorities who they are in advance of their journey.


Could we one day see the return of large yachts to Cuban waters?

And there is also the spectre of the Russian intelligence service, which is active in the area. “A lot of people that own very big boats are of Eastern European origin and they might not want their information being captured by Russian government entities.”

But Thompson was at pains to emphasise that the country itself is “very safe” and that owners should not be put off by the prospect of visiting this destination. However, Cuba does remain a security state and visitors should be mindful of this. “I would stay away from allowing the crew to replenish the boat or repair anything but if you anchor off the coast, tender in and see the sights, it’s a beautiful place with wonderful people…it’s definitely worth it but there are things you should definitely take advantage of before going into Cuban waters and putting passengers on dry land in Cuban waters and it’s not that costly.”