Because of the heavy regulation of direct flights to Cuba (licensed flights, especially for Cuban-Americans in Miami) most independent US travelers simply pass through Canada or Mexico. As Jackson says "Maybe I'll go through Mexico, Old Jesse Helms don't have to know". The Cubans, helpfully, issue visas on a loose slip of paper, so no stamp is placed in your passport.
The bans on US citizens or residents traveling to Cuba have been in place for almost 50 years, despite being opposed by most of the US population and, in recent years, most Cuban-Americans. They are enforced by the US Treasury's Office of Foreign Asset Control (OFAC), a body which supervises US sanctions on a number of countries, including Sudan, Iraq, Iran, Burma and Cuba.
However the shift in OFAC activity in recent years, regarding Cuba, has been from travelers to internet transactions and from individuals to companies. The change is striking under the Obama Administration, but it was already happening under the Bush Administration.
In 2003 (when 84,000 US citizens visited Cuba) 240 individuals were fined for Cuba-related offenses. This fell to 31 in 2008 and 3 in 2009, when there were only 40,000 US visitors each year. At the same time, the corporate focus increased. OFAC records tell us that the 99 fines in 2008 netted $3.5 million, while the 27 fines in 2009 netted a huge $772.4 million.
The total fines include some for other countries like Iraq and Iran, but in 2009 all the big fines were for companies doing Cuba-related business. Credit Suisse was fined a massive $563 million, Lloyds $217 million and the ANZ bank $5.75 million, in the latter case for transactions involving both Sudan and Cuba.
Of the individual fines in 2003, most were for attempting to
import Cuban cigars, along with some for financial and currency transactions. Even
the 240 fines that year meant that less than one in 300 of US travelers to
Cuba faced a fine, mostly for being silly enough to take a box of Cuban cigars
through US Customs.
Most fines result from "agreed' penalties or settlements, but occasionally there has was a hearing. A lawyer for the blockade-busting group "Pastors for Peace' said they had successfully contested several "fine for travel' cases, probably some of the five listed by OFAC in 2003.
In 2008, most of the 31 individuals fined for Cuba-related offenses were purchasing
Cuban cigars on the internet; travelers hardly appear in the 2008 lists. In
2009 the three fined individuals included one purchasing cigars on the
internet, one for a financial transaction and a third for a property
transaction. Important changes have taken place in OFAC enforcement.
Additional restrictions on travel were introduced by the Bush Administration in 2004, including measures which blocked many student groups and limited family visits by US citizens of Cuban origin. As a result, US visitors to Cuba almost halved between 2003 and 2004. While the Obama Administration removed many of the additional restrictions on family visits, it is not yet clear to what extent this has overcome the general fear of travel to Cuba, instilled by the Bush Administration measures.
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