According to Newsweek’s article: Don’t Stop Hoarding Those Cuban Cigars Just Yet, even though the U.S. and Cuba are working toward normalizing diplomatic relations, it doesn’t look like there will be an ample supply of legal Cuban Cigars anytime soon.
The new rules allow American travelers to return with up to $400 of Cuban goods, of which only $100 can be alcohol or tobacco for personal use. Secondly, many major cigar companies have created dual trademarks which will create legal conflicts with these companies. Lastly, the FDA may cause problems with the Tobacco Control Act unless they change regulatory power over cigars.
So it sounds like your best option is to shop Bobalu Cigar Co. and buy premium hand rolled cigars that rival any cigars from Cuba.