When the United States imposed an embargo on Cuba in 1960, American travel to the Caribbean island that lay just 90 miles to the south began grinding to a halt. What had been a veritable playground for America's gangsters, celebrities, and the moneyed jet-set, as easily accessible for quick weekend trips as it was for longer leisure vacations, suddenly became frustratingly forbidden.

The language of the embargo is confusing; despite popular references to a “travel ban,” the embargo does not expressly prohibit travel. Instead, it forbids spending money “in transactions in which Cuba or a Cuban national has any interest... including transactions related to travel.” But many Americans aren't even familiar with the terms of the embargo; they are simply unaware they can travel to Cuba if they do so with an approved organization or tour operator that has been licensed by the US Department of the Treasury's Office of Foreign Assets Control, the body responsible for overseeing interpretation and enforcement of the embargo.

Under current terms of the embargo, there are eight categories of travel that are licensed; these categories range from family travel to travel for professional research and journalistic work. The licensed forms of travel also include a category popularly referred to as “people to people” travel, a category whose boundaries have expanded during the Obama administration. During the Bush administration, Americans could travel to Cuba with educational, religious, humanitarian, or cultural organizations holding a US government license. In 2011, Obama reinstated and then increased the scope of Clinton-era travel regulations to include licenses for nearly any type of non-profit organization or for-profit tour operator interested in leading Cuba trips as long as it could substantiate that it would implement “a full-time schedule of educational exchange activities that will result in meaningful interaction between the travelers and individuals in Cuba.”  

When the “people to people” category was reintroduced and expanded, more than 100 organizations and outfitters—many of which had never led Cuba trips previously—applied for licenses, and an unprecedented number of those licenses were granted. The (US) National Trust for Historic Preservation was one of the non-profits granted a license; National Geographic Expeditions and Friendly Planet were among the commercial tour operators who began leading Cuba trips.

Though Americans who want to travel to Cuba legally have more options than they have enjoyed in the past 50 years, as with any type of trip, it's important to know what your choices are and how to make smart decisions for a meaningful and memorable visit. Travelers who have been on authorized people-to-people trips offer some firsthand tips about how to choose an operator and what to prepare for in order to have the best experience.

Ask about the itinerary

Meta Reid, a children's librarian, traveled to Cuba with tour operator International Expeditions. She recommends that Americans who are interested in traveling to Cuba on a people-to-people tour ask the operators or organizations with which they are considering traveling for a detailed itinerary before booking. “You'll want to have at least one or two things that will really interest you,” says Reid, whose trip included a number of cultural and artistically-focused activities, such as seeing rehearsals of a ballet company and jazz group, having lunch at an organic farm, and meeting a librarian in Havana.

Choose an agency that will handle logistics for you

Donna Mikeska, who also traveled on an International Expeditions tour, says that choosing an organization or operator who handles your paperwork for you is preferable to handling logistics on your own. “The process seems difficult and we did not have to deal with any of this; it was done for us by IE,” she says. When considering an operator, ask what logistics they handle and what preparations you're responsible for.

Pack your patience

Mikeska also recommends packing patience and practicing flexibility. From clearing Customs at the airport to reacting to unforeseen schedule changes, Mikeska says attitude is everything. Challenges and frustrations are a feature of traveling in Cuba, and a good dose of patience and humor goes a long way.

Adjust your expectations

Mikeska's husband, Gerry, who long dreamed of traveling to Cuba and signed up with International Expeditions within 24 hours of receiving an email notification that the operator was offering a Cuba trip, urges prospective visitors to adjust their expectations. Given the economic impact of the embargo, he says, “some hotels were in need of paint [and] lost electricity,” though he notes, “others were very upscale.” The variety and quality of food are typically poor, so he advises travelers who seek creature comforts to consider another destination.

Engage in people-to-people encounters

Gerry Mikeska also recommends taking as much advantage as possible of the “people-to-people” contact with locals. Most operators pair with local guides, and for Mikeska, “the knowledge gained from being able to ask questions and converse with [local guide] Edelso was 50% of the trip for me.” Donna Mikeska and Meta Reid agree that one-on-one conversations provided some of the most meaningful memories from their Cuba trips.

Travel outside Havana

While Havana could be a destination in and of itself (and is for many people-to-people tours), Donna Mikeska recommends booking a trip with an operator who offers itinerary options beyond the Cuban capital. “It is important to travel to various towns to get a real feel for the country. There are so many other areas that deserve a visit, so selecting a tour group that travels about the island would be best,” she says. One of the trip highlights for her was SCUBA diving in the Bay of Pigs.

Don't be an ugly American

Curiosity and the desire to experience an “unspoiled” Cuba are what compel many Americans who travel to Cuba to visit the island. Be curious and ask questions, the Mikeskas urge, but act with the same courtesy you'd exhibit anywhere else. Their top tips? Don't take photos without asking permission and bring small gifts, especially art or school items or small toiletries, to share with hosts and locals you'll meet during your trip.

Share your stories

Travelers who have participated in people-to-people trips say they feel informed and inspired by their experiences, and enjoy sharing stories of their travels with others. Some even become involved in advocacy to call for an end to the embargo. “I hope with a little more effort from Cuba and the US that the embargo can be lifted, travel unrestricted, and a brighter future for Cuba can develop,” says Gerry Mikeska.

Julie Schwietert Collazo is a freelance writer based in New York City.

 

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