The 78ft Numarine yacht 'Still Water', docked in Marina Hemingway close to Havana last week, carrying 12 American guests having crossed the Straits of Florida, after a departure from Key West.
Relations between the two countries have evidently improved despite Paul Madden, a Palm Beach broker, having to spend the past eight months trying to get the green light to enter Cuban waters.
The passengers and crew on board had to enter the country on a person-to-person permit, one of 12 different ways American citizens can bypass the ban on visiting Cuba. Currently, non-American flagged yachts are free to visit but are then not permitted to enter US waters for the next six months.
Fifteen people are on board (12 guests and 3 crew members) with guests including a Wall Street Journal reporter and a documentary filmmaker. They are all staying on board the yacht and are hoping this week to enter Havana Harbour.
While Madden is clearly adventurous, he also knows the pitfalls and has gone on record to stay that he 'wants to tread very carefully'. Adhering to the 12 visa requirements has been a pre-requisite and he is elated to have made history with this journey.
It is hoped that tourism to the region will be boosted by this news, with ferries from the States hoping to capitalise on the opportunity and achieve the same result.
Mr Madden received his license on July 1 - which was the first license issued by the U.S. Office of Foreign Assets Control to operate ferries to Cuba.
According to reports, other companies have received their licenses including Carnival Cruise Line but it was Madden and his 78-foot yacht that was the first to sail between the United States and Cuba in more than fifty years.
Superyacht Still Water received a professional research license from OFAC and the U.S. Commerce Department and the whole trip was arranged by a New York educational tour guide called Academic Arrangements Abroad.
The Obama administration has sought to restore diplomatic ties with Cuba and as a result, cruise and ferry companies have been desperate to get their hands on government licenses. But a major logistical reason for the delay in commencing the service is that most Cuban ports have very shallow depths.
In addition, insurance costs have been a particularly grey area and Mr Madden and his maritime lawyer said that this was their biggest challenge. While they declined to say how much they paid, they did say that since the area is unknown and this is the first time a yacht has entered Cuban waters in more than half a century, the insurance rules were being written anew.
Madden declined to say how much the trip cost but said the average charter price for a yacht that size and the length of the trip is about $45,000.
If you are thinking of embarking on a yacht charter to Cuba, then considering the rules and regulations that must be adhered to, it would be wise to contact a yacht charter broker to do further investigation for you.
Take a look at the fleet currently available for a luxury yacht charter to Cuba.