How many times can one travel to Cuba?

I'm currently using Support for the Cuban people. I met my girlfriend during my last trip, she's Cuban. Can I use family visits to visit her?

Strictly only if you marry her or have a child together.

But that is the category that is least likely to be subject to any checking.

However:

What about Cuban immigrations? When they see your US passport coming back and forth so often, do they ask you the reason why you keep going to the island?

• I would think that "visiting my girlfriend" would be a perfectly acceptable justification to Cuban immigration.

I'm currently using Support for the Cuban people. I met my girlfriend during my last trip, she's Cuban. Can I use family visits to visit her?

Strictly only if you marry her or have a child together.

But that is the category that is least likely to be subject to any checking.

Cool. Thank you.

@bobmichaels you never had any issue from CBP, OFAC or US authorities when returning from Cuba? I'm really thinking to keep going back and see all the island while Obama rules applies. I mostly spend time photographing their landscape, learning their culture and visiting their museums. I traveled under Support for the Cuban people. I wish I can go for more time, but I have to work. Lol.
What about Cuban immigrations? When they see your US passport coming back and forth so often, do they ask you the reason why you keep coming to the island?

@bobmichaels you never had any issue from CBP, OFAC or US authorities when returning from Cuba?

CBP has no responsibility for enforcing Cuban travel regulations. They are consumed with immigration issues.
OFAC is 200 employees in WDC consumed with Iran, Syria, Sudan, Afghanistan, North Korea, ISIS, Al Quaeda, and about 100 specifically named terrorists. They has no resources to devote to Cuban travel.

What about Cuban immigrations? When they see your US passport coming back and forth so often, do they ask you the reason why you keep going to the island?

Yes, they will ask. But returning to visit your girlfriend is perfectly acceptable. They will ask her name and details. Just make sure you never lie to them as they seem to know everything.

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