Do yourself a favor and layover for a day in Mexico. Staying 24 hours reduces the chances the authorities in your transit country will send passenger manifests for incoming flights to the US. Mexico is just more lax as well.

http://www.visitlatam.com/latin-amer...us-safely.html

They don't need to follow you around a Canadian airport, as they have the full manifest long before you land. All they need to do is put names to faces.

Going through Mexico is one way to get to Cuba, but Costa Rica, El Salvador, any country is good. Just make sure the flights are separate, as far as laying over a day, that's not important. Fly American or whatever round trip to El Salvador, then TACA round trip from there to Havana. Don't use credit cards while there and your chances of getting "caught" are slim to none.

Travel to Cuba is a violation of OFAC unless you have specific permission. It used to be a $100 fine if we discovered your travel to Cuba upon entry into the U.S. There was a questionaire as well.

o CUBA-RELATED TRAVEL TRANSACTIONS - Only persons whose travel transactions fall
into the categories discussed below may be authorized to spend money related to
travel to, from, or within Cuba.

http://www.treas.gov/offices/enforce...ascii/cuba.txt

How to keep a dictatorship in power in one easy lesson...

Santo Domingo's a good bet, if you don't mind flying Cubana

Viva Fidel!

Generally, it's easier to go through Cancun or MEX since there are more flights and it's easier to match up to your eventual US destination. But these def will work as well.

OK, here's a different scenario that I don't think anyone has brought up.

What if you hold dual-citizenship?

Can US authorities still bust you even though you traveled to big bad Cuba on a non-US passport?

Yes, they can. No doubt about it. Dual citizenship does not provide any sort of pass with respect to your obligations as a U.S. national (citizen or resident alien).

Bruce

Here's an interesting "what-if": Suppose John Smith is a dual-citizen of an EU nation (jus sanguinis) and the US (jus soli) (and say his permanent residence is in the EU, but he does own a vacation home in Colorado - he likes to ski, but has an aversion to Switzerland ). Mr. Smith is a management consultant, and the majority of his income is earned in the EU. He's paid in euros, and his primary bank is EU-based. Mr. Smith, being a well-off globe-trotting sort of guy, has a US-based bank account as well (which he uses to pay the mortgage on his vacation home) - it's mostly funded by his EU work, but he does periodically consult with US-based folks who pay him in $, and he puts his US-earned income in this account.

Is he in violation of the policies if he flies from the EU to Havana, spends his euros, flies back to the EU, then comes to the US a few weeks later?

Is he still a US citizen when setting foot on Cuban soil?

That's your answer.

So, if my parents (non US) bought a ticket for me, and pre-paid room and board in Cuba, then I can proudly tell the CBP that I just went to Cuba and tell them to pound sand, right?

This Cuba embargo nonsense is as nonsensical as Daylight Savings. They both need to be scrapped. This whole thing's ridiculous.

If you have family in Cuba, you can easily get permission to visit. No need to be sneaky in that case.

Bruce

You don't need family in Cuba, as long as someone NOT from US paid everything for your Cuba trip, it should be ok.