Hi there, and congrats on deciding on a DW! We never considered Cuba for our wedding, but we considered Mexico, Dominican, and Jamaica. We found that the requirements to legally get married in Mexico and Dominican were nearly the same. Jamaica however, seemed to have the easiest and cheapest process and no documents need to be translated to a different language. We eventually decided on Jamaica after finding a resort we fell in love with! It can be super overwhelming at first. Try making a list of what is important to you in a resort (ex, big vs small, free wedding vs non free wedding, price for guests etc). Also, try searching on here for different resorts and you will find tons of info! Good luck and happy planning:)