[ofalkaed]

No, not even civilians need to do that. Ultimately the only time you have to is when there is documentation of your being in the a foreign country and if there is no documentation you probably don't want to draw attention to yourself. This is why so many people where able to go to and from Cuba when it was technically illegal, US and Cuba agreed to not document/stamp the passports of private citizens.

[umanwizard]

It is still technically illegal to go to Cuba without a specific whitelisted reason (and tourism isn’t on the list). It’s just not strictly enforced.

[ofalkaed]

So it is not illegal? you just need to go through the proper bureaucracy as you do with every countries. Last I looked into it a few years back it was easy to get the paper work, one person I found who went there just signed up for guitar lessons in Havana to study Cuban guitar, showed the paperwork for the guitar classes and was good to go because it was for educational reasons even if the guitar lessons only accounted for a tiny portion of their time there. The white listed reasons are fairly broad and easy to work within, sure you can't just hop on a plane for a weekend visit but that is true of many countries that no one would say it is illegal to go to.

[umanwizard]

The point is nothing has changed about the legality. It has always been allowed to go for one of these whitelisted reasons, you just had to apply in advance.

Now it is still legal to go for exactly the same set of reasons, they just don't bother actually checking. There's no "paperwork" you need to get; you just tell the check-in agent which legal reason you fall under.

[ofalkaed]

I have only researched this from the standpoint of going there by private boat which is different and has some extra work including getting approval from the USCG but what I picked up about general travel is that doing the paper work allows you to take a direct flight, can save you from headaches down the line and offers some protection from headaches caused by how this changes in the future. What changed is how the law is enforced, not the law itself and this changes every decade or so.