For Americans (persons of U.S. jurisdiction), travel to Cuba for “tourist” activities remains prohibited by statute, but there is a lot of flexibility to enjoy Cuba within the boundaries of U.S. rules.
You do not have to fly to Cuba through Canada or Mexico as some people did years before the rules changed.
There are 12 categories of authorized travel to Cuba. The Department of Treasury’s Office of Foreign Assets Control (OFAC) has issued general licenses in all 12 categories of authorized travel, subject to appropriate conditions. This means that individuals who meet the regulatory conditions of the respective general license they seek to travel under do not need to apply for a specific license (ie. time consuming process) from OFAC to travel to Cuba.
Required Cuban travel visas can be easily obtained from your airline or tour operator for about US$75.
Mandatory Cuban health insurance is typically included in your flight or tour purchase.
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All you have to do is self-certify (ie. fill out a simple form typically given to you by your airline or tour operator).
The 12 categories of authorized travel to Cuba are: family visits; official business of the U.S. government, foreign governments, and certain intergovernmental organizations; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances, clinics, workshops, athletic and other competitions, and exhibitions; support for the Cuban people (this is the “people-to-people” category most travelers opt for); humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or informational materials; and certain authorized export transactions.
Cuban cigars and rum:
U.S. citizens, authorized to travel to Cuba, may purchase alcohol and tobacco products while in Cuba for personal consumption while there. Authorized travelers may return to the U.S. with up to $100 worth of alcohol or tobacco or a combination of both. Products acquired in Cuba may be in accompanied baggage, for personal use only.