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Written by  Christopher P. Baker


President Obama’s reinstatement, in January 2011, of a Clinton-era license category-”People-to-People”-permitting any U.S. resident to participate in legal group travel to Cuba, combined with an end to Bush-era restrictions on island visits by Cuban-Americans, has sent U.S. visitor numbers to Cuba soaring.

In addition to the reinstatement of Specific Licenses for People to People organizations and a General license for visits with relatives by Cuban Americans, President Obama also issued a General license for academic travel by educational institutions which again allows travel by undergraduate and graduate classes with a ‘structured educational program’ in Cuba for any length of visit, as long as the students are receiving credit for their visit.

A General license was also issued for religious travel by any member or members of a ‘religious organization’ as authorized by that organization, and without the need for a separate application to OFAC.

Last year, the USA was second only to Canada as the largest source of Cuba’s 2.84 million visitors. And in March 2013, Miami outstripped Canada as the primary source of flights to the Communist Caribbean island nation.

Dozens of U.S. tour companies and academic and cultural organizations now offer People-to-People (P2P) programs on a regular basis, including Abercrombie & Kent, National Geographic Expeditions, and Tauck Tours, plus Cuba specialists such as Insight Cuba. Although most such programs focus on Cuban culture, special-interest trips span the spectrum from birding to photography workshops. Last year, Texas-based adventure motorcycle touring company MotoDiscovery was even licensed to offer the first U.S. group motorcycle tours of the Communist island since the Revolution in 1959. This winter Havana’s flagship hotels will resound to yanki accents, with only rarely another foreign language to be heard.

The P2P programs have opened the window to generic Cuba travel a crack. However, most U.S. restrictions on travel to Cuba remain in effect.

Legal travel by individuals, for example, is limited to a few narrowly defined categories, such as journalists, academics and students, or for professional research, religious or humanitarian purposes. Such individuals may travel under licenses issued-most on a case-by-case basis-by the U.S. Treasury Department’s Office of Foreign Assets Control (OFAC), which oversees all regulations related to Cuba travel and trade.

Except as specifically licensed by OFAC, arrangements and payments of any kind in connection with travel to Cuba are prohibited, including to companies in third countries. The restrictions (which are applied under the 1917 Trading With the Enemy Act) apply to all individuals and companies under U.S. jurisdiction, anywhere in the world.

Criminal penalties for violating the regulations include up to ten years in prison, one million dollars in corporate fines, and up to US$250,000 under the Trading with the Enemy Act, plus civil penalties up to $65,000 fine under provisions of the 1996 Cuban Liberty & Democratic Solidarity Act (Helms-Burton Bill).

Licensing Required
The travel industry’s involvement in Cuba-related travel is tightly regulated and policed.

OFAC regulations state: “Any person subject to U.S. jurisdiction who provides services akin to those of a travel agent with respect to Cuba (for example, arranging travel to, from, or within Cuba, selling tickets for flights to Cuba, or reserving and selling accommodations for authorized travelers within Cuba) must be specifically licensed by OFAC as a Travel Service Provider.”

Travel companies can apply to OFAC for a Travel Service Provider (TSP) license, permitting the holder to make commercial travel arrangements to Cuba on behalf of P2P and other authorized travelers:

People-to-People programs, for example, operate under tightly defined regulations, which preclude “tourism” and recreation and require “a full-time schedule of educational exchange activities that will result in meaningful interaction between the travelers and individuals in Cuba.” That means itineraries packed with formal encounters, from lecture-room presentations to visits with tobacco farmers, theatrical groups, and the like. Trip participants are not permitted to excuse themselves on a whim for what OFAC terms “self-directed” activities.

Any travel corporation or incorporated individual can apply for a license to operate P2P programs, which function as tours in all but name. (More than 140 entities hold P2P licenses.) Applicants for P2P licenses must provide a sample itinerary. Once approved, tour companies are free to design itineraries as they wish, as long as they adhere to the types of educational exchange activities described in the application. Companies that specialize in recreational activities, such as Backroads (which received a P2P license earlier this year), are specifically barred from including purely recreational activities.

P2P license holders are not permitted to make their own travel arrangements directly with Cuba - they may only make arrangements for travel to Cuba through a TSP license holder, or with travel service providers that are located outside the United States and not subject to U.S. jurisdiction. Nor may TSPs arrange or offer their own “educational exchange” tours. Thus, travel agents and tour operators can apply for a P2P or TSP license, but not both.

Bush-era restrictions on advertising and commissions have been eased to permit P2P license holders to publicly promote their programs. And such companies can now pay travel agent commissions for bookings. However, travel agents who are not licensed as TSPs or P2P providers remain barred from advertising or promoting Cuba-related programs and flights, although they may arrange and promote their own “educational exchange” programs to Cuba by piggy-backing with a P2P license holder.

How to Get There
Licensed travelers may fly direct to Cuba from the USA. About two dozen Carrier Service Providers (CSPs) are authorized by OFAC to fly direct charters to Cuba using aircraft operated by American Airlines, JetBlue, SkyKing, World Airways, and United Airlines. At press time, 12 U.S. airports were licensed to permit flights to Cuba, although Fort Lauderdale, Miami, New York, and Tampa are the only ones with flights currently in operation. (The average cost round-trip from Miami is about $450, including a Cuban tourist visa and mandatory travel insurance.)

Thousands of other U.S. citizens sidestep the restrictions to savor the frisson of the forbidden by traveling to Cuba through Canada, Mexico, the Caribbean, or Central America aboard foreign airlines. However, all returning citizens from other countries are required to fill out a U.S. Customs and Immigrations form which requires listing all countries visited during the trip abroad. Not answering truthfully may be considered a felony.

With regard to non-TSP travel agencies and tour operators: “They may be able to provide services for [non-licensed] travelers, such as travel arrangements to third countries, from where a traveler makes his or her own arrangements for travel to and within Cuba,” claims Michael Krinsky, a Cuba specialist in the New York-based law firm of Rabinowitz, Boudin, Standard, Krinsky & Lieberman. Treasury Department regulations do not “show a clear penalty against travel agents who book travel this way,” says Krinsky.

The regulations change frequently, however, and are open to interpretation by OFAC staff. Travel agents should double-check the regulations with OFAC before proceeding
with a reservation.

Except as specifically licensed by OFAC, it is illegal for any U.S. resident or company to make payments in connection with travel to Cuba through websites. Hence, U.S. websites such as and are barred from displaying Cuba-related flight information and from accepting reservations for Cuba flights. Even the U.S. websites of foreign-based airlines that serve Cuba, such as Air Jamaica, Copa and Grupo Taca, are tailored to please Uncle Sam and thus no longer display their Cuba flights.

Cuba Cruises
Meanwhile, cruise companies wait in the wings. U.S. law prohibits any vessel that carries passengers to or from Cuba from entering a U.S. port without OFAC authorization. It also prohibits any vessel that enters a Cuban port from entering a U.S. port for 180 days from the date the vessel departed Cuba, regardless of the ship’s registry. Thus foreign, as well as U.S., companies are effectively barred from a cruise destination that offers vast untapped potential.

Nonetheless, several foreign cruise ships have featured Cuba on their itineraries. Currently, England’s Fred Olsen Cruise Lines includes a two-day Havana stopover on its 15-day Caribbean cruises from Barbados aboard the Braemar; Thomson Holidays’ 1,500-passenger Thomson Dream stops in Cuba on its Caribbean itineraries; Germany’s Aida Cruises occasionally includes Havana on its peak-season programs; and Canadian newcomer Cuba Cruise launched in 2013 with week-long cruises December through March aboard the 970-passenger Louis Cristal (the ship departs Montego Bay, Jamaica, and calls at five Cuban ports).

U.S citizens, however, are barred from booking such cruises. Hence, earlier this year Boston-based tour operator Road Scholar was forced to cancel a launch of cruise-based P2P trips aboard the Louis Cristal after OFAC warned that such trips were illegal. Only 90 miles separate Key West from Havana, yet in many ways the Florida Straits is the widest moat in the world.

Cuba, however, seems to be betting that the metaphorical distance will soon be narrowed. In 2012, it initiated construction of a 1,200-slip marina and cruise port-one of the Caribbean’s largest marinas-at Varadero, the island’s main beach resort, 90 miles east of Havana. And in March 2013 the Cuban government announced plans to add 20,000 hotel rooms by 2020 to its current stock of 60,500 rooms. Meanwhile, Cuba’s five state-run hotel companies have been steadily upgrading their facilities to meet North American standards. And since 2011, when state-monopoly restrictions were lifted, the number of private restaurants-paladares-has exploded, adding vitality to a previously lackluster scene.

In 2006, gravely ill, Fidel relinquished the reins to his younger brother Raul. After skillfully shoving aside Fidel’s partisans, Raul initiated radical reforms in 2011 to promote private enterprise and kick the moribund Communist economy into gear.  A “new” quasi-capitalist Cuba is slowly emerging. Possibility hangs in the air like intoxicating aromas of anejo rum.

This winter’s U.S. visitors to Cuba do so at a fascinating historical moment.
Christopher P. Baker is the author of Moon Cuba Handbook and National Geographic Traveler Cuba. He promotes himself through his website,

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