We went via jamaica when we were on L1 2 years ago. No issues coming back in - the CBP officer didn't mention it when we had it on our customs form that we had visited

I know there are flights from Florida to Cuba, and American citizens of Cuban descent are permitted to visit family (maybe once a year).

I'm under the impression that a US citizen can also apply for a visa to visit Cuba, but must book through a travel agent for a package holiday, which does not permit free movement in Cuba.

I looked into visiting Cuba as a UK citizen, but it seems the visa is only valid if I fly from London (could be wrong, or things have changed since I looked).

You don't need a visa as a UK citizen, are you a PR in the US? If so you'd be under the same restrictions no matter where you arrived from.

Don't think you have to use a travel agent and package anymore. With the loosening of things and some scheduled flights now permitted, seems using Jetblues website anyhow, one can just book the flights directly on their website.

They start HAV to FLL in a couple weeks.

(Obviously one would still need to be allowed to go to Cuba, but doesn't appear you need to use a travel agent for these new scheduled flights.)


American will let you directly book as well but unlike Jetblue, they remind you before booking about the 12 reasons you would be permitted to go.

Family visits
Official business of the U.S. government, foreign governments and certain intergovernmental organizations
Journalistic activities
Professional research or professional meetings
Educational activities and people-to-people exchanges
Religious activities
Public performance, clinics, workshops, athletic or other competitions and exhibitions
Support for the Cuban people
Humanitarian projects
Activities of private foundations or research or educational institutes
Exportation, importation, or transmission of information or informational materials
Travel related to certain authorized export transactions

UK citizens do need a visa to travel to Cuba. It's called a tourist card and isn't permanently fixed to your passport (possibly because they're aware of the difficulties this might cause with US authorities on entry to the US, who knows!) but it's a visa nonetheless.

So realistically, a US resident / USC cannot easily take a holiday or go site seeing in Cuba.
"Criminal penalties for violating the Regulations range up to 10 years in prison, $1,000,000 in corporate fines, and $250,000 in individual fines. Civil penalties up to $65,000 per violation may also be imposed."

Easily? Yes they can, if they join an educational or cultural tour, which are offered by many providers. Considering the number of my friends and acquaintances who've been in recent years, some on an annual basis, I'm guessing it's fairly "realistic."

Just one example - 2017 International Book Fair of Havana: a Cuban Journey for Librarians, Bibliophiles and Writers