Travel to Cuba

A friend and I are planning a trip to Cuba later this year, our situations are slightly unique so i'm wondering how we'd go about entering, exiting and reentering the U.S.

Case 1-Me

I am a South African citizen that resides in the U.S. I hold a green card and of course use my South African passport to travel since they dont issue American passports to permanent residents.
My plan is to enter Mexico using my South African passport (do i need a visa to enter Mexico as a South African?) then travel to cancun and take a passenger liner to Cuba. I'll have them stamp my South African passport on entry and exit to Cuba and then cross back into Mexico and reenter the U.S using my green card. I'm worried about officials at the border asking to see my passport and seeing a mexican exit stamp and cuban entry/exit stamps in it, though i've heard to get back into the U.S all they ask to see is a green card.

Case 2-Friend

My friend is a dual Bulgarian/ American citizen, our plan was to have him enter mexico as a bulgarian (again, does he need a visa?) and then exit mexico as well as enter and exit cuba back to Mexico using that same Bulgarian passport. The problem i see with this is when we reenter the U.S, his American passport will have no stamp in it to say he entered mexico as he used his bulgarian passport to do that. And of course if he shows his bulgarian passport there'll be cuban stamps and a mexico exit stamp in it. Is there any way to get around this?

Also, i'm does anyone know of a decent passenger liner that travels between cancun (or any other mexican port close to the U.S border) and a port in cuba.

When I was in Cuba back in 2002, Cuba did not stamp passports. Therefore, there is no "proof" to the U.S. that you entered Cuba. Can anyone who has been recently confirm that?

Greg

Cuba does not stamp passports in or out, you are complicating everything. Bulgarian and South African passports from Cancun to Cuba and back, after you have your Cuban visas issued in Mexico. As far as a visa for South Africans travelling to Mexico, check with the nearest Mexican Consulate. Do you have solid reservations for this "steamboat" from Cancun..I have never heard of this service..is it new..or it is something another traveller told you about?

Yes, actually a college aquaintance told me that ships occasionally run between Mexican ports and Cuba, apparently he booked passage on one and recommended it as a cheap way to travel. I dont have class with him anymore so i cant get the details. I'm not sure if he somehow got passage on a cargo ship or just on a regular passenger ship.

Ships between Mexico and Cuba do not exist. Only way for you to travel here will be using either Click-Mexicana or Cubana Airlines.

Cuba does not stamp passports if you are coming with your tourist card (re: tourist entrance visa) which you can purchase while in Cancun for around $15.00. But just in case as your passports will not be Americans when landing in Cuba if you see that the Immigration officer is going to stamp your passport, explain to him your peculiar situation as a US resident. Cuban Customs and Immigration has special instructions not to stamp AMERICAN passports.

Keep in mind that you will need to avoid a second entry stamp to Mexico when going back from Cuba. Some bend a $20.00 bill inside the passport so Mexican officials get happy. It has been working for a lot of my American friends during the last 10 years.