Went to a couple of SSCA seminars recently. In the past it was not to hard to get there and back. Soon it will be easy. Just now a LOT of attention is being paid in the area. The wet foot/dry foot policy is only in effect until relations are normalized. So BOTH sides are looking closely.
For US people/boats, the legal way is to fall into one of 12 categories (NOT hard to do) and you must depart the US, stay no longer than 14 days, and return to US directly.
Hope this helps.
Greg