Americans entering Cuba from Canada and then going through US Customs?

Bob the return thru Montreal is not quite so friendly, I still feel like a criminal even tho I have not actually been bothered for several years.... This might be true of all entries into the taciturn northern climes......

Hi beasamel! Can you follow up with a post on your experience? Did Cuba stamp your passport upon entry/exit? I've been reading that they are now doing so but was wondering if I could ask them to not stamp it.

Also, what did you end up saying to the custom's agents at the US border and how did it go? Thanks!

I've been reading that they are now doing so but was wondering if I could ask them to not stamp it.

Of course you can but no one can guarentee that request will be honoured.
Statistically one can almost guarantee all this is irrelevant.

Remember that the overwhelming majority of Americans who visit Cuba do so legally. If you are one of those small numbers who go without a license, do not tip them off by acting guilty when they are probably are assuming you are innocent.

But do people who go through legally with a license have to show the license to the US border people? I'm just wondering what the best course of action would be at the US border if Cuba does stamp my passport...

Dear Beasamel:

Use your head:

#1. You went to Cuba to visit "Family"
#2. You have a half sister who lives in Habana.
#3. You went to take your Family much needed medicine.
#4. You stayed with family NOT in a resort.
#5. You travel thru Montreal because you can't stand Miami.
End of story.

But do people who go through legally with a license have to show the license to the US border people?

I have never been questioned or asked to show my license. I also have never had anyone comment about my 3 full pages of Cuban immigration stamps.

But do people who go through legally with a license have to show the license to the US border people?

A general licence is not something that you actually apply for and receive as a bit of paper.
So IF someone e.g. has family in Cuba and choses to travel there via Mexico or Canada or the moon they are travelling under the general licence provisions of ODAC.
Why not actually read the actual OFAC regulations?

I have been to Cuba over 20 times and the last 2 times Cuba stamped my US passport (April and September).

I always lied to customs and I always looked forward to it but you can't lie with a stamp in the passport. My passport has extra pages and it full of stamps but still it is there if they look so I said I was in Cuba.

First time. "I met a girl on the internet". Agent said he "wasn't going to bust my balls" and advised me to get a permit if I plan to go back"

Second time. I was taken into the secondary inspection. Lots of questions. I filled out the OFAC forms. I joke that I have a girlfriend in Cuba and any fine you possibly give me is cheaper than my divorce. After 30 minutes I overhear an annoyed voice "I got a guy born in PA here who has been to Cuba 12 times, nobody cares, why should I?". Then after another 15 minutes "So are you going to prosecute or not? So you don't care? Should I just let him go?" Then he comes out and let me go. I never said I was there 12 times but that is approx. how many times I was there via Canada so they certainly have access to flight manifests, etc... (cuba->canada flights pass over US airspace so they know you were there if they want to look)

(Note: For me this is part of the adventure. I'm always super cooperative, positive, friendly, honest and open with customs officials because I have nothing to hide. I just think it is ridiculous I can't go to Cuba for something that happened 60 years ago)

Unless you have a very good excuse (your sister lives in Montreal for example) to explain yesterdays Canada entry stamp by air in your passport don't lie. Tell them you were in Cuba. It is illegal to go to Cuba but nobody cares. The worst they will do is question you for a while. Definitely don't bring any souvenirs and it would help to say something stupid like "Obama made it legal".

People on these Amtrak trains get stopped carrying dope/guns/slaves/etc every day. Maybe some questions if you admit travel but get caught lying and you are missing that train.

Dear Beasamel:

Use your head:

#1. You went to Cuba to visit "Family"
#2. You have a half sister who lives in Habana.
#3. You went to take your Family much needed medicine.
#4. You stayed with family NOT in a resort.
#5. You travel thru Montreal because you can't stand Miami.
End of story.

Lying to a federal officer is a felony and they are trained to tell if you are lying and ask follow up questions. Giving them an elaborate false back story is a terrible idea. Just tell them you went to Cuba as a tourist. Decline to answer any other questions and decline to fu=ill out any forms. As a US citizen, they have to let you in to the country. They worst that will happen is that they will yell at you and bluff and tell you that you are in big trouble if you don't answer this question or fill out this form, but it's an act.