Stop Worrying...No American will be Prosecuted
This is part of the testimony under oath of Richard Newcomb, Director of the Treasury Department Office of Foreign Assets Control (OFAC) given to the Senate Foreign Relations Committee on February 11, 2002.
"Prior to 1992, OFAC lacked civil penalty authority to enforce the Cuban embargo. Criminal prosecution was extremely rare. In my experience, U.S. Attorneys often do not accept travel violations for criminal prosecution absent other illegal commercial or financial transactions by the traveler involving Cuba or Cuban Nationals. The lack of criminal prosecutions is widely reported in the media and in almost any travel publication that discusses Cuba.
With the passage of the CDA in 1992, the Trading With the Enemy Act ("TWEA") was amended to provide civil fines of up to $50,000 (now adjusted to $55,000 for inflation) could be levied for violations of the Regulations. The CDA also required that he Secretary of the Treasury impose such penalties "only on the record after opportunity for an agency hearing...with the right to pre-hearing discovery. In 1996, the LIBERTAD ACT increased the number of categories of violations for which civil penalties may be sought to include all travel related violations. In February 1997, OFAC promulgated proposed regulations to govern the hearings, and in March 1998 published the final regulations. Judicial review by Article III courts is available once the Administration Law Judge's civil penalty determination is made final.
As of 2014, no Americans have been prosecuted for traveling to Cuba for a vacation or to visit family.