The Cuban Civil Aviation Authority has for years very generously issued free permits for private pilots flying their own aircraft for pleasure. Effective immediately, these free permits are now available only to aircraft with a MTOW of 3,000 kgs or less (6,600 lbs or less). Heavier aircraft must pay the commercial overflight fees.
Pilots can contact Cuba directly for the permits and pay Cuba if charges apply, according to the U.S. Treasury Department. Most pilots, however, will not know how to apply for a permit nor how to pay for the permits. Please disregard AOPA and FltPlan.com warnings that pilots cannot contact Cuba directly for their permits. This is incorrect information. Do not pay $362 or more for a Cuban overflight permit that is available for $39.95.
For a $39.95 annual membership in the most widely used pilot's guide for the Bahamas and Caribbean, Caribbean Flying Adventures.com, private pilots flying their own aircraft with less than 3,000 kgs MTOW will receive a free roundtrip overflight permit. For aircraft with a MTOW above 3,000 kgs with the owner at the controls and flying strictly for pleasure, the roundtrip fee will be $235. This fee is essentially "at cost" plus a $40 service fee. Caribbean Flying Adventures will wire the fees to the Cubans in Euros on behalf of the pilot (the wire transfer fee alone can cost up to $100).
Cuba will likely limit the number of free permits for the same plane during the year but the frequency has not yet been specified. Down and back the same day or back the next day is not considered a pleasure flight.