View from across the water at the ferry port in Regla
It is perfectly legal for Americans to travel to Cuba without applying for permission in advance as long as your trip falls within one of the 12 allowable reasons. If you are doing a self guided trip it may be more economical to travel through another country. Of all the Lonely Planet guides I have referenced for any of my travels the one on Cuba has been the most valuable. I would recommend obtaining a Cuba edition and reading through it during planning and well in advance of your trip. It outlines everything (visa requirement, money, etc). If however you have questions about my personal experience please feel free to ask.
San Francisco de AsisAs of this writing your American phone, iPad etc., will not work in Cuba even if you would be willing to pay roaming charges. It will say “no service” the entire time you are there unless you are connected to wi-fi and wi-fi is not readily available. I was fine other than the one hour of wi-fi time I purchased to let my family and friends know that I was alright I did without internet. I did all of my research prior to arrival and printed out whatever I thought I’d need. If you are someone who absolutely needs to be constantly digitally connected you may have a problem.
Cash is King. Your US credit card/debit card will not work in Cuba and if you exchange USD for Cuban currency you will pay a 10% penalty. At the time I was there the going rate for the USD was .96 cents to one CUC with the additional penalty it worked out to about .87 cents rounded up. I brought GBPs and Euros I had from some of my other travels and a non US debit card for use at the ATM. Plan carefully if you don’t want to run out of money because you’ll have to bring all the cash you think you’ll need with you. Although I did see a Western Union I would not plan on using it. Some people chose to purchase Canadians currency prior to going to Cuba instead of having to exchange US dollars.
Most everyone is friendly just be aware that the hustle is real. Cuba is a safe country and though you will probably not get mugged you should definitely look out for smooth talkers who want to separate you from your money (the technique is not as abrasive as I’ve encountered in other countries but it’s there) pay attention, you’ll recognize it. I almost wished I had visited prior to the internet age. I didn’t see any homeless people. Everyone seems to want more material things. In my opinion sometimes more is just more and not always better. (Maybe I think that because I’m working my way towards minimalism). But what do I know? I am just a visitor, I do not live there year round.