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I was there for work in 2005 with IBM and it was a major PITA as a US citizen, and I had a travel authorization/license from the state department since we went to a lot of countries like this.
None of your credit/debit cards will work by default, you need a pre-loaded debit card from an issuer outside of the US. The next issue was really nothing besides the hotel took our debit cards. I had to use borrowed Canadian dollars from a co-worker which he had to exchange at a nasty rate for local currency.
The Canadians and Euros in my group had an easy time, me, not so much. Without a "stamp" or a entry license you can get slapped with a nasty fine coming back to the states. The US travelers I had dinner with at the hotel came in from Mexico and were doing everything possible to leave no "trail" of their trip to Cuba, electronic or otherwise.
It was an interesting place on the days off I had, but I honestly had an easier time getting around the ME and China then I did in Cuba. If I was on vacation I don't think I would want this hassle. But again the Canadians in my group LOVED it there and were staying for an extra few days after the job was up.
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2021 Model Y
2005 Cayenne Turbo
2012 Panamera 4S
1980 911 SC
1999 996 Cab
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