One wild card is Havana. As some analysts have noted, this announcement puts the onus on Cuba to further open relations. In response, Fidel Castro seemed to downplay the significance of the move, noting that the Obama administration has limited some "odious restrictions" upon travel, but has not said a word about the trade embargo that has hamstrung the island nation. In context, the Cuban government's response seemed somewhat dismissive and petty.
In his Cuban Missile Crisis speech, President Kennedy famously referred to Cuba as "that imprisoned island." Over the years, the name has stuck, but it has become somewhat unclear as to who, exactly, is doing the imprisoning. For anybody who remembers the Cold War, it is easy to see why a Communist dictatorship would be inclined to limit visitors to and from its shores. After all, it's hard to maintain the sham of a worker's paradise when Cuban car owners are scrambling for makeshift parts and wealthy American visitors are wearing flashy consumer goods.
However, the biggest impediment to Cuban travel hasn't been the Castro regime. From 1962 to 1977, the United States legally barred its citizens from traveling to Cuba. President Carter allowed the travel restrictions to expire, but President Reagan reestablished the trade embargo. Combined with subsequent restrictions, it became all but illegal for U.S. citizens to spend money in Cuba, and thus nearly impossible to travel there.
While this policy has kept American dollars from entering the Cuban economy, it has also resulted in an embargo on American ideas and ideals. For a country that prides itself on the strength of its governing philosophy, this has undermined the United States' ability to act as a strong counter to Castro's Cuba.
For that matter, in the context of America's close economic relationship with China, its determination to give Cuba a 46-year "time out" is odd at best and startlingly hypocritical at worst. Under the circumstances, one has to wonder about the extent to which the Cuban-American community's alleged support of this policy is influenced by its impressive sugar cane holdings. After all, a Cuba that could freely trade would be be more politically open, but would also represent an economic threat to America's sugar farmers.
The Obama administration's willingness to crack open the door to Cuba seems to make both good political and good economic sense. It has the ability to rewrite the "America as bully" script that has characterized Cuban/American relations for the past 46 years, even as it offers hope for dissidents in Castro's crumbling island empire.