Advice for using points to Cuba

Actually AA just started allowing award flights to Cuba to be booked, unfortunately for OP they don't start flights there until the beginning of September.

http://thepointsguy.com/2016/06/redeem-aadvantage-miles-flights-to-cuba/

If you get lucky one of the other US airlines may open up award tickets shortly. I doubt they will get flights going before AA, but it's possible United will open up award ticket booking soon. Potentially, that would allow you to book a partner award on Copa routing through Panama.

The other option is to book a separate ticket to a 3rd country, like Mexico or Panama, and then book an award ticket to Cuba on from there using a foreign award program. Theoretically, you may even be able to do this on one award ticket. I've heard of at least one case where someone was able to get foreign airline to book them an award ticket from the US to Cuba via a 3rd party by calling a non-US call center. Technically this was against the rules because even foreign airlines weren't allowed to book flights from the US to Cuba on one ticket. However, with the recent changes, this rule may no longer be in effect. This route would probably involve some lengthy calls with foreign call centers since this is all very new and may not be possible.

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