Cuba Air Charters

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Cuba Charter Flights

A global leader in private jet charter, Windsor Jet Management offers flights all over the world including the United States, Asia, Africa, Canada, Europe, the Middle East, Central and South America. With a vast fleet of private aircraft based in South Florida, Windsor Jet is one of the select few operators now offering direct flights into the beautiful destination of Cuba. For many years Cuba has been inaccessible from the United States. Now with the recent rules and regulation changes, the country is now open for tourism and business travelers to come and explore the historic, beautiful island and we want to take you there.

We are proud to announce that Windsor Jet now offers inbound and outbound flights to the incredible island of Cuba direct through our home airport KFXE. Getting there has never been easier when you fly with us. So wherever you are in the world, we will pick you up and take you there on your time and in style.

Treat yourself to a getaway with beautiful landscapes, unforgettable sunsets, historic landmarks and where mojitos were born. Fly to Cuba with Windsor Jet and we guarantee you’ll have an amazing stay.



After arriving in Cuba via private jet charter, get yourself stationed and enjoy the history and the most beautiful beaches in the area.

Cuba’s colorful capital, Havana, is known for the Spanish colonial architecture of its 16th-century Old Havana core, including Castillo de la Real fort, now a maritime museum, and the pre-revolutionary Capitolio. American-made cars from the 1950s line the city’s streets and rumba groups play in the painted alley Callejón de Hamel. Salsa emanates from clubs and cabaret is still performed at the famed Tropicana.

Just 90 miles between U.S. and Cuba, visiting this island has been banned for U.S. Citizens for many years. Now you can get in touch with the people and the culture of Cuba through our cultural and educational programs.

Discover the way former U.S. President Carter met the people of Cuba; the spots visited by Beyonce and Jay-Z on the Island and get a revival of the days the American writer Ernest Hemingway lived in Cuba. You don’t need to be a superstar or a politician to travel legally to Cuba.

Join us in this journey to the biggest island in the Caribbean, where Cubans will present us with the best of their culture, history and the roots that make us so different, yet so close.


Passenger Considerations:
Current U.S. Department of the Treasury regulations, specifically administered under the Office of Foreign Assets Control (OFAC), permit crew and passengers to enter Cuba provided that the purpose of the trip falls into one of 12 approved categories of travel. Many of these categories are now vaguely defined, allowing a wide range of purposes of travel to qualify. Note that ‘tourism,’ for example pure sightseeing, going to the beach, etc., is not an authorized purpose of travel. Passengers must have an itinerary that meets one of the permitted reasons for travel. The reference and recent update to this policy can be found here:
Treasury and Commerce Announce Further Amendments to the Cuba Sanctions Regulations

Aircraft Operations:

Current U.S. Department of Commerce regulations, as defined in the Export Administration Regulations, allow for any US registered aircraft (Part 91 or 135) to fly directly to and from Cuba, provided the aircraft both depart from, and return from one of the 22 authorized airports (see below). Regulations further allow the export of equipment and spare parts (to be used only on another US registered aircraft that may have a mechanical issue in Cuba).

Approved U.S. Ports of Entry for Flights to and from Cuba

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