Can I sail to Cuba?

Yes, in fact, this may be the only way that you can travel to Cuba! Only group tours are permitted after recent changes in travel permissions by the United States.
For the last couple of months, Cubans have been renting out their houses “Airbnb-style” as “Paladars.” However, since Americans staying in these accommodations aren’t travelling with a certified group- this style of travel will no longer be permitted.
Cruises, on the other hand, provide people-to-people guided group tours that will still be permitted under the new rules. This means that as long as you book your group tour through the cruise line your tour will be in accordance with the law and you will be able to visit. This is very similar to the status of people cruising to Russia.