Foremost, all travel excursions offered you by Bespoke Cuba Travel strictly adhere to the US State Department and US Treasury Department’s Cuba travel policy guidance and rules.

Many people are confused about if, and how, they can travel to Cuba legally.  The answer is, yes it is ‘very’ legal for US citizens and residents to visit Cuba.

Historically the rules for travel to Cuba from the United States have constantly shifted depending on which political party holds the US Presidency. Republican administrations use Presidential Orders to tighten the embargo restrictions while democratic presidents use the same to loosen them. It’s a political seesaw. On November 9, 2017 President Donald Trump’s administration revised President Barack Obama’s 2014 Cuba policy. Most of the revisions are related to conducting trade with and making investments in Cuba. The changes leave in place most of the travel measures that President Obama introduced. In fact, contrary to popular belief, little has changed for Americans interested in visiting Cuba. Renowned Travel blogger Ciara Johnson recently published that it was so easy to visit Cuba, “like any other trip out of the country.”

Despite what you may have read, in 2018 US airlines added more direct flights to Cuba. Cruise lines added new US departure ports and additional weekly cruises to the island. US Travelers are still able to spend unlimited amounts of money throughout the island and bring back nearly anything they wish, i.e. Cuban rum, cigars, souvenirs, textiles, furniture, art, etc. (provided they do not exceed standard US customs limitations).

Regardless of how minimal the changes to travel rules, there are guidelines you MUST keep in mind.

1- With few exceptions, Americans are prohibited from visiting Cuba on their own as was the case under Obama. The current administration ordered the Treasury Department to strike individual people-to-people travel to Cuba. Travelers may no longer visit Cuba independently, they must do so as part of an authorized Group tour.

2- Bespoke Cuba Travel provides travel services for any travelers who qualify for any of the 12 categories of authorized travel to Cuba which include: Family visits (§515.561); Official business of the U.S. government, foreign governments, and certain intergovernmental organizations (§515.562); Journalistic activity (§515.563); Professional research and professional meetings (§515.564); People to People Educational Travel (§515.565); Religious activities (§515.566); Public performances, clinics, workshops, athletic and other competitions, and exhibitions (§515.567); Support for the Cuban people (§515.574); Humanitarian projects (§515.575); Activities of private foundations or research or educational institutes (§515.576); Exportation, importation, or transmission of information or informational materials (§515.545); Certain export transactions that may be considered for authorization under existing Department of Commerce regulations and guidelines with respect to Cuba or engaged in by U.S.-owned or -controlled foreign firms (§§515.533 and 515.559).

Most US travelers who visit Cuba from the US under the People to People Educational Travel ( §515.565) Support for the Cuban People

(§515.574) and Humanitarian projects (§515.575) classifications.

3- Although BCT journeys provide you with opportunities to sit by the beach and sip mojitos, “tourism ” can no longer be the sole purpose of your trip. The new rules being that you must improve the lives of the Cuban people and engage in meaningful interactions with them. Activities such as staying at an Airbnb (casa particular) and shopping at stores and dining at private restaurants (paladares) owned and operated by self-employed Cubans (cuentapropistas) are first hand examples of financial support for the Cuban people. While visiting a film set and becoming acquainted with the actors, sharing your respective vocabulary with each other, planting an organic garden at a pediatric cancer clinic and cooking alongside Cubans all provide the rich engagement that is required. BCT’s motto alone, “More Cubans fewer tourists,” underscores those directives.

4-  Perhaps the most recent and paramount change to US Cuba Travel policy is the US State Department’s addition of Prohibited Financial Transactions with Cuba’s military and Communist party officials. This list forbids travelers from conducting business with certain entities. The objective is for travelers to do business directly with Cuban owners of small businesses as opposed to entities that would disproportionately benefit the regime at the expense of private enterprise.

The list includes 80 hotels (out of 4500+ hotels and Airbnbs available in Cuba) and approximately 100 businesses and government organizations. Examples are 2 jewelry stores, real estate companies (US law prevents you from buying property in Cuba anyway), certain government agencies such as the Ministry of Interior, one shopping mall, etc. One must be careful when heeding the list. What appears to be a small private business could easily be a business owned by a communist party leader. However, the tourism sector is largely  owned and managed by non-military Cuban organizations, multinational corporations and private Cuban individuals. This list represents less than 10% of all the businesses on the island.

5- One policy term Cuba travel companies and travelers often disregard, is the mandate that travelers keep records of their activities and expenses while in Cuba. It’s critical for all travelers to Cuba to maintain good records of their schedule, hold onto all receipts and be able to provide evidence proving they engaged “in meaningful interaction between the traveler and individuals in Cuba”  AND that they provided, “support for the Cuban people.”  US Immigration and Customs officers infrequently request this information from travelers upon arrival in the US. Further, the US Treasury Department mandates travelers hold onto those records for at least 5 years. Although Trump suggests he’ll stringently enforce his new rules, the chances of the US Government requesting this information from you years after your return from Cuba are low. The above makes traveling to Cuba a bit cumbersome if not a little risky for the disorganized. Rest assured, BCT keeps track of all of this information for you.

On your last night in Cuba, Bespoke Cuba Travel will provide you with a very comprehensive journal-like report detailing the schedule of your respective activities, copies of business cards of Cuban businesses the group patronized, pictures of your engagement with Cubans, receipts, proof of your donations, etc.  In addition we will email you a pdf version of the above for your electronic records. Bespoke Cuba Travel is the only Cuba travel provider that provides guests with such an exhaustive record.

Below are links to the Office of Foreign Assets Control websites associated with the US Government’s Travel Policy as related to the US -Cuban embargo:


2 (Section II)


4        The comprehensive Cuban Assets Control Regulations (Section 515); excerpt from the complete US Cuba Embargo Policy:[1]


If you have further questions on how to travel legally to Cuba, please

get in touch with us or call the Treasury Department directly at 1-800-540-6322 Press #1 for English & Option #6 for the Cuba Travel desk. They are very helpful (you will likely be asked to leave a message; they respond quickly).

Although Reading all 168 pages of Section 515 would be very informative, it is not required reading provided you peruse 1-3. Nevertheless, Sections 515.560 – 515.576 of the Cuban Assets Control Regulations deal explicitly with the travel policy.