You can travel to Cuba many different ways. Some folks prefer a group tour and others like traveling alone. There are benefits to each style of traveling. The complexities of traveling to Cuba (especially as an American) can be hard to figure out on your own.
If you are traveling from America under a “Support for the Cuban People” general license from OFAC (U.S. Treasury Department) you will have to fulfill a few obligations. For example, you are required to have a full-time itinerary, abide by the restricted list, and keep all of your receipts for at least 5 years. Most licenses have the same basic requirements, but some details vary within each license. Having an itinerary professionally designed will help you find the best happenings and most importantly keep you legal in your travels to Cuba.