Until recently, direct flights from the U.S. to Cuba were not available. And while it's still difficult to get a direct flight, travel restrictions have been reduced, allowing people to visit their relatives in Cuba or to travel there for a few other limited reasons. It's important to go through the proper channels, however, as flight to Cuba is still rather restricted.
Obtain the correct documents and licenses to visit Cuba legally. If the trip is to visit family living in Cuba, you can apply to obtain a Cuba Family Visa. If you are traveling there for other reasons, you may apply for correct documentation from the U.S. Department of the Treasury, Office of Foreign Assets Control (OFAC) or the United States Interest Section, Havana, Cuba. The U.S. Interest Section website offers all the forms necessary for a request under the Cuban Family Reunification Parole Program.
Find out if you qualify for travel to Cuba. It is illegal to travel to Cuba for a weekend fun trip, but you may qualify for another legal reason. Traveling to Cuba to visit family living there is now allowed with restrictions. You must apply for a visa, and you are limited to one trip every three years. Other qualifying factors include religious organizations, humanitarian work, journalism and some business travel. Check with the Office of Foreign Assets to ensure that you qualify.
Contact a travel agent to help plan your travel to Cuba, as there are few flights that fly direct. Most flights will take you out of the U.S. before flying to Cuba, but there are a few flights that fly from Miami to Havana.