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Here is the information from TIMATIC as of today for someone with an Indian passport traveling to Cuba on a flight or ship from the US. This is the system that airline personnel check to ensure you have your immigration documents in order before allowing you to check in for your flight. It clearly indicates that Cuba will require a visa and does not indicate that it can be bought upon arrival, so I would expect you'd need to show it at check in. I don't know if there are implications upon return to the US if they notice you're arriving from Cuba - I would hope not but I don't know. Talk to an immigration lawyer if you have questions on that.
Information as of 14JUN17 / 1520 UTC
National India (IN) /Embarkation USA (US)
Destination Cuba (CU)
Passport required.
- Passports and other documents accepted for entry must be valid on arrival.
Visa required.
Additional Information:
- The length of stay must be covered by USD
- Photocopies of visas are accepted for entry in Cuba. The sponsor must be at the airport upon arrival with the original visa.
- Residence permits issued by Malta must be biometric.
Warning:
- Visitors not holding return/onward tickets and other documents required for their destination could be refused entry.
- All visitors are required to hold travel insurance to cover their medical expenses while in Cuba. The travel insurance must be bought before departure to Cuba.