It appears that it is currently (as of May 2016) impossible to get a permission from the U.S. for a solo tourist visit to Cuba.

However, in various older questions, users have stated that you can easily avoid the strict US travel restrictions by flying into Cuba from another country (such as Mexico or Canada) and avoiding getting an entry stamp in your U.S. passport.

According to the Embassy of Cuba in USA website:

Tourist Visa (Tourist Card)

The Tourist Visa or Tourist Card is only for purposes of tourism to Cuba. It is valid for one single entrance into national territory for a 30-day trip and can be extended for an additional 30 days at the office in the hotel where one has accommodations or with the immigration authority.

To obtain this visa in person at the Consulate, these documents are needed:

-Valid Passport

-Plane Ticket with entry and return dates

-Payment of the Consular fee for this service

As far as I can tell, the Cubans don't seem have harsh tourist travel restrictions for U.S. citizens.

However, according to some very old information on Wikitravel,

While in the past Cuba did not stamp US passports, allowing US travelers to visit Cuba without detection from their government, Cuba recently started stamping US passports as a matter of policy.

In light of the recent diplomatic relations, have Cubans tightened loopholes for U.S. tourists traveling without the blessing of the U.S.? Does Cuban customs still exempt entry stamps for travelers with a U.S. passports?

  • Note: this isn't a dupe of the question I linked to, which was asking about tourist travel sanctioned by the White House. This question is about avoiding those restrictions, which have been routinely avoided by U.S. citizens Cuban customs up until a few years ago.
    – crypdick
    May 12 '16 at 0:39
  • 2
    Bring a bunch of books with you and give them away. Problem solved! May 12 '16 at 3:19
  • So you are asking about breaking the law and whether you can get away with it?
    – user102008
    May 12 '16 at 6:10
  • As I write this I am drinking a beer and browsing the net in Mexico, which is breaking laws in Saudi Arabia and North Korea. I'm ok with that. If I go to Cuba and I am not breaking any local laws I don't really care what any foreign government thinks about it. Cuban customs as of a few years ago had a different procedure for US citizens, and if you look, there are various up-voted answers on this very site instructing US citizens to travel via Canada or Mexico. See meta.travel.stackexchange.com/questions/3464/…
    – crypdick
    May 12 '16 at 16:44
  • 2
    That answer is an answer to the question "for what activities does the US permit US citizens travel to Cuba". That is not the question I'm asking now. I'm asking: if I, a US citizen, independently travel to Cuba (via Mexico, for example) will the Cuban customs let me in /regardless of what any foreign government thinks about that/ (given the context that US citizens have been able to travel like that for decades)
    – crypdick
    Jun 18 '16 at 23:16