Cuba is one of the most restrictive countries in the Caribbean for drones. Import by arriving travelers is generally prohibited, and there's practically no legal way for tourists to fly their own drone. Bringing one anyway risks confiscation at the airport.
Importing drones and drone components as an arriving traveler is explicitly prohibited by Cuban customs. Legal private use is limited to members of the Cuban aviation club, commercial use ('Trabajo Aéreo') runs through the state enterprise GEOCUBA. There's no regular path for tourists to fly their own drone.
For special cases like professional film productions, a permit is theoretically possible, but requires sign-off from several institutions and takes 4 to 6 weeks or longer. This isn't practical for a normal vacation trip, the request would need to go through the Cuban embassy well in advance.
Flying is generally prohibited within 8 km of airports, in military zones, over crowds and at night without special permission. No public, complete map of all restricted zones exists.
If a drone is discovered at customs, it's usually confiscated. Storage is typically free for a few days, then fees apply. Getting it back on departure is possible but slow and not guaranteed, some travelers report nearly missing flights due to the bureaucratic process.
Unauthorized flights can be fined between 2,000 and 5,000 Cuban pesos, with a 50% increase for repeat offenses. The drone can additionally be seized.
Based on everything I researched, I'd leave the drone at home for a normal trip to Cuba. The risk of confiscation is high, and there's practically no legal path for tourists. Anyone needing professional footage should contact the Cuban embassy at least 6 to 8 weeks before departure.