The recent loosening of restrictions on the right to travel to Cuba has permitted almost any American to go there. You no longer have to apply to the Treasury Department--or to anyone else, for that matter--for a "license" to do so. If you honestly and validly feel that you are going there for any of 12 non-touristic reasons--religious, educational, professional, humanitarian, and the like, and not to simply look around or lie on a beach--you can pick yourself up and go. No one will prosecute you for making that honest decision (and hardly anyone was ever prosecuted for going there even before the formal restrictions were largely lifted).
So how do you get there? In the immediate aftermath of the decision to loosen restrictions, a company called Cuba Travel Services announced that it would operate weekly flights every Tuesday from New York City to Havana. And by the time you read this, there will undoubtedly be other firms operating flights to Havana from several other U.S. cities.
But it isn't necessary to go there on a non-stop flight. You can already fly to Cuba from almost any U.S. city, by going via a stop in Kingston, Jamaica, in Cancun, Mexico, or in Nassau, The Bahamas. In those intermediate cities, you simply change planes to a local flight going from there to Havana. So the job of getting to Cuba isn't difficult at all.
Where do you stay once there? Nearly every major hotel in Cuba has a website listing its prices and, in many cases, enabling you to make a reservation online. Trouble is that the supply of non-resort hotels (namely the beachfront hotels for recreational stays) in Cuba is quite limited, and it is expected that a surge in American travel to Havana, in particular, will cause the Cuban hotel industry to show itself as sold-out on many dates.
Enter AirBnB.com. Just recently, the president of that firm that procures spare rooms in apartments for persons traveling to hundreds of cities both at home and abroad, announced with great fanfare that AirBnB.com has arranged to make no fewer than 1,000 apartment rooms available to Americans traveling to Cuba. These accommodations in private homes, known in Cuba as "casas particulares", are regarded as more than sufficient to house the early numbers of American tourists. Although the comfort of such lodgings may not equal what you'd find in a hotel, they should nonetheless prove sufficient for unpretentious Americans.
So that leaves one further possible step to take, as to which there is much confusion. When individual tour companies announced air packages to Cuba, they explained that the high price they were asking for round-trip flights was explained by the fact that those prices included a mandatory purchase of Cuban medical insurance, to cover health treatments and emergencies that might arise during your stay. One firm indicated--without specifically saying so-- that their round-trip price included as much as $400 for the purchase of mandaory medical insurance.
I seriously doubt--it's only my opinion, as yet without a factual basis--that explanation. In calls to such prestigious travel insurance firms as TravelGuard, I have been told that a very comprehensive policy of insurance for a trip to Cuba--one that involves not simply medical insurance, but every other sort of travel insurance like trip cancellation, interruption, and the like--will cost less than $200. And I have found other travel insurance firms that will charge you less than $30 for a medical insurance plan only, which they claim will enable you to enter Cuba.
I have found other firms stating that if you arrive in Cuba without medical insurance, the immigration officials will direct you to an airport office which will sell you a Cuban medical insurance policy priced at $4.50 for every day of your projected stay in Cuba. Once you pay that minor sum, you are permitted entrance to Cuba.
And I have found all sorts of Canadian air-and-land packages to Cuba that pose no requirement at all for medical insurance. The entire subject, in sum, seems to be confusion incarnate. Until the Cuban government announces specific requirements, if any, for medical insurance, I would simply purchase a standard policy from any recognized travel insurance company, and I would present proof of that policy to the Cuban immigration personnel on arrival. And if I were only slightly impetuous, I would fly to Cuba without any such policy, planning to purchase one--if necessary--on arrival at Havana airport. I very much doubt that the Cubans--desiring, as they do, additional tourism--will turn away any well-meaning person, or persons offering to buy such a nominally-priced policy on the spot.