Image: A boy cleans his father's car on a street in Havana
Desmond Boylan  /  Reuters
A boy cleans his father's car on a street in Havana. For the first time since the 1959 revolution, Cubans will have the right to buy and sell cars in a much-anticipated reform under President Raul Castro, another step toward greater economic freedom on the Communist-led island.
updated 10/13/2011 8:27:27 AM ET 2011-10-13T12:27:27

Despite its location 90 miles off the shores of Florida, Cuba remains, in the eyes of many Americans, one of the last great travel mysteries. Since 1961, when the U.S. government instituted a de facto Cuban travel ban, visits to the country by U.S. nationals have been problematic, if not impossible. American travelers without legal means of visiting the island have been compelled to choose other destinations or circumvent U.S. law by traveling via a third country.

Recent moves have widened the goalposts significantly. Since 2009, Cuban-Americans on family visits, plus any other interested parties traveling with a valid license, have been able to take advantage of less stringent Cuban travel restrictions when planning sorties to one of the world’s most unique, stoic and culturally vibrant societies. In January 2011, the license process became a lot easier with the re-introduction of government-sanctioned people-to-people trips that were discontinued in 2003.

But, before you iron the creases out of your guayabera shirt and get ready to reacquaint yourself with mambo dancing, Guantanameras and real cigars, it is important to do some pre-trip homework. To travel legally to Cuba, U.S. citizens must first be in possession of a valid license. The U.S. Department of the Treasury currently issues two types of license — "general" and "specific" — catering largely to academic institutions, religious organizations, journalists and people engaged in humanitarian work. "Specific" licenses must be applied for in writing and are dealt with on a case by case basis. Check the Treasury website to see if you qualify.

The recently reintroduced people-to-people program reflects efforts by the U.S. government to engage U.S. citizens in "purposeful travel" to Cuba by bringing them into contact with ordinary Cubans in the hope of bolstering trust and mutual understanding between the two countries. On these trips, authorized agents handle the license paperwork, leaving participants with fewer legal worries and more downtime to enjoy organized excursions in a similar way to vacationers from Canada and Europe.

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Already this year, the U.S. Treasury department has issued licenses to 35 travel companies to organize people-to-people trips, including travel pioneers Insight Cuba which first ran excursions to the country during the Clinton era and returned in September 2011 after an enforced seven-year hiatus. Insight’s guided trips focus on art, music, history and the outdoors, and prices start at around $3000 for seven-night itineraries.

Another recent development has been the introduction of more charter flights serving Cuba from the U.S. Prior to January 2011, only three U.S. airports (New York City, Los Angeles and Miami) ran regular Cuba charters, but in the last few months several new airports (including Chicago and Atlanta) have added authorized flights for licensed travelers.

Story: New Orleans airport approved for Cuba air service

To minimize disruption in a country which has no formal diplomatic relations with the U.S., various specialist organizations have grown up to smooth the way for first-time Cuba travelers seeking guidance and advice. One of the oldest and most trusted is Marazul, a travel agency founded in 1979 that helps both individuals and groups with license inquiries, flight bookings, hotel reservations and in-country transportation.

One of the most complicated issues for U.S. travelers in Cuba is money. U.S.-issued credit and debit cards are not accepted by Cuban banks and changing U.S. dollars incurs a 10 percent commission. Consequently, it is advisable to change sufficient cash funds into Canadian dollars or euros prior to your visit and store your money in a money belt and/or hotel safe-deposit box when in-country. Furthermore, licensed travelers are restricted to a State Department spending allowance set at $179 per day since 2008.

For most visitors the hassle of reaching Cuba is well worth it. Castro’s withered time-capsule promises to be like nowhere else you’ve ever visited: economically poor but culturally rich; visibly mildewed but architecturally magnificent; infuriating but at the same time strangely uplifting. Even better, most Americans are surprised to find that ordinary Cubans bear them no animosity. You will be welcomed with open arms — and by some of the best music on the planet.

This story, US to Cuba travel: widening the goalposts, originally appeared on

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