BIS issued a new rule today, June 5 called “Restricting the Temporary Sojourn of Aircraft and Vessels to Cuba”
US Part 91 private flights: Effective June 5, you cannot operate an N-reg aircraft privately to Cuba for any reason. This includes Corporate. It doesn’t matter if your passengers meet the “category requirements”, it’s a no go.
Part 135 Air Ambulance: You can go, and you don’t need a license. From the rules: “Air ambulances operating under 14 CFR part 135, may depart from the United States under its own power for any destination”. “Air ambulances will remain eligible for the license exception when destined to Cuba”.
Part 135 Charter: The new rules are difficult to understand but as this type of operation is covered under the section referring to AOC Holders. You can operate as normal.
Part 129: Foreign operators can operate as normal, no change.
Part 121: Airlines can operate as usual, no change.