The United States first placed an embargo on Cuba in 1960. Since then there has been an economic, financial and/or commercial embargo in place in full or partially. Each President and each year brings changes either tightening or loosening the restrictions, recently the Obama administration has agreed to allow Cuban Americans with relatives in Cuba to travel to the country to visit family.
Since we don't have any relatives in Cuba we had to figure out another way in. And although Cuba wants tourists and has no problems with Americans entering the country they aren't able to accept US credit cards which throws a big wrench into trying to make hotel and air reservations.
This also meant that we had to take as much cash as we would will need for our entire vacation, no debit cards or ATMs are available to Americans. Additionally US dollars are being taken out of circulation there so the charge to exchange them is very expensive. We chose to bring both Canadian and Mexican currencies with us to exchange which seemed to work out well but did involve some pre-planning.
Most people assume that flying through Canada is the best way to go since Canadians can legally travel there but what many people don't know is that Canada shares flight manifests with the US. The best ways of entry are Mexico or the Caribbean Islands. We chose a non stop flight from Seattle to Cancun on Alaska Airlines. Earning mileage for travel to the Forbidden Island? Priceless! There are only 2 flights a day to Havana and since there is a 3 hour layover required to fly the same day, we chose an inexpensive hotel and spent the night. We flew on Christmas day, met Forest at the hotel and that evening was spent in warm Cancun, drinking margaritas decorated with gum drops and eating tacos and ceviche.
We took the advice from a friend who had gone a couple of years ago and had a really good experience using a US based travel agent who specializes in helping Americans into the country. Don't ask me how all this works, I'm sure we don't want to know! I really can't say enough about our agent Madison and all she did to help us out. She arranged our flights from Cancun to Havana and gave us options of sending a check or using a credit card that she would run through another agent in the Caribbean. She told us which counter to go to and the name of the person to ask for to pick up our tickets in the Cancun airport. I won't lie, this was the first time I felt uneasy and unsure, what if we got ripped off? Doesn't this all sound so clandestine?
But everything was just as she had said and our tickets and tourist visas were all there. The only glitch we encountered while checking in for our flight was that Forest had to pay a departure tax since she had been there for more than 24 hours which we still aren't really clear about.
On to lodging... our friend's sister had recently stayed in Havana at a private casa particular and had contacted her family. Although they didn't have any availability they recommended and contacted Luis and Luisa for us. We paid cash upon arrival for our room. Our travel mates Forest and Tim booked their casa online, also paying in cash upon arrival. We arranged for a driver to meet us at the airport and drive us into town using that site too.
Booking a hotel for our last couple of days proved to be a bit more complicated as no one could take a US credit card. We booked our stay at the Hotel Sevilla thru this site but had to use our French friend's credit card. Madison could have also booked our room but since it was the high season her connections just didn't have anything available in our price range.
Our worries were completely unnecessary though, the passport control in Seattle barely glanced at our passport as he welcomed us home and customs agents waved us and our suitcases packed with rum through lickety split.
Hope this information helps! I'm happy to answer any other questions you might have.